CID 2554 Carbamazepine

Structures Structure depictions of this compound, including computationally generated two-dimensional (2D) and three-dimensional (3D) structures, as well as experimentally determined 3D single-crystal structures.

2D Structure A two-dimensional (2D) structure representation of the compound. Because this structure is processed through chemical structure standardization (Hähnke et al., J. Cheminform. 2018, 10, 36), it is not necessarily the same as the structures provided by individual data contributors. https://doi.org/10.1186/s13321-018-0293-8 true 199 true

3D Conformer A three-dimensional (3D) structure representation of the compound. This 3D structure is not experimentally determined, but computed by PubChem. This structure may or may not be the same as the inherent structure of the compound you would expect to see in vacuum or in the gas phase, because the underlying computational algorithm aims to generate a protein-bound structure, which would be observed in a protein-ligand complex. More detailed information on this conformer model can be found in Kim et al., J. Cheminform. 2013, 5, 1. https://doi.org/10.1186/1758-2946-5-1 true 199 Carbamazepine 2554

Crystal Structures This section provides links to crystallographic information from various sources. Subsections 2 Name Value true 1

CCDC Number A 6- or 7-digit-long numeric identifier assigned to the crystal structure in the Cambridge Crystallographic Data Centre (CCDC). https://www.ccdc.cam.ac.uk 180 CCDC Number http://doi.org/10.5517/cc67gd8 185919 181 CCDC Number http://doi.org/10.5517/cc8d2d3 249934 182 CCDC Number http://doi.org/10.5517/ccnfx43 609185 183 CCDC Number http://doi.org/10.5517/ccpbnd1 635853 184 CCDC Number http://doi.org/10.5517/ccvkx4f 791775 185 CCDC Number http://doi.org/10.5517/ccwb9q6 814268 186 CCDC Number http://doi.org/10.5517/cc1178yh 960316 187 CCDC Number http://doi.org/10.5517/cc1178zj 960317 188 CCDC Number http://doi.org/10.5517/cc11790l 960318

COD Number An identifier assigned to the crystal structure in the Crystallography Open Database (COD). https://www.crystallography.net/cod Columns 13 COD Number https://www.crystallography.net/cod/2107460.html 2107460 14 COD Number https://www.crystallography.net/cod/2300327.html 2300327 15 COD Number https://www.crystallography.net/cod/2311081.html 2311081 16 COD Number https://www.crystallography.net/cod/2311083.html 2311083 17 COD Number https://www.crystallography.net/cod/4509215.html 4509215 18 COD Number https://www.crystallography.net/cod/4509220.html 4509220 19 COD Number https://www.crystallography.net/cod/4509221.html 4509221 20 COD Number https://www.crystallography.net/cod/4509222.html 4509222 21 COD Number https://www.crystallography.net/cod/4510731.html 4510731 22 COD Number https://www.crystallography.net/cod/4510732.html 4510732 23 COD Number https://www.crystallography.net/cod/4510733.html 4510733 24 COD Number https://www.crystallography.net/cod/7106548.html 7106548 25 COD Number https://www.crystallography.net/cod/7227180.html 7227180 26 COD records with this CID as component 1505213 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=1505213 1505214 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=1505214 1506790 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=1506790 2019240 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2019240 2021730 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2021730 2107456 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2107456 2108741 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2108741 2205799 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2205799 2205821 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2205821 2205976 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2205976 2216052 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=2216052 4500002 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500002 4500003 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500003 4500004 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500004 4500005 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500005 4500007 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500007 4500008 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500008 4500010 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500010 4500011 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500011 4500012 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4500012 4502452 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4502452 4503359 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4503359 4508997 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4508997 4509211 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509211 4509212 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509212 4509213 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509213 4509214 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509214 4509216 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509216 4509218 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509218 4509219 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509219 4509223 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4509223 4512300 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4512300 4512301 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4512301 4512302 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=4512302 7201712 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7201712 7201984 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7201984 7203285 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7203285 7206693 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7206693 7209625 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7209625 7209657 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7209657 7212585 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7212585 7228537 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7228537 7228538 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7228538 7228539 0 7 https://pubchem.ncbi.nlm.nih.gov/substance/?source=Crystallography+Open+Database&sourceid=7228539

Associated Article Publication associated with the crystal structure of the compound. Typically it is the paper in which the crystal structure was originally reported. 13 Associated Article Sovago, Ioana; Gutmann, Matthias J.; Senn, Hans Martin; Thomas, Lynne H.; Wilson, Chick C.; Farrugia, Louis J.. Electron density, disorder and polymorphism: high-resolution diffraction studies of the highly polymorphic neuralgic drug carbamazepine. Acta Crystallographica Section B 2016;72(1):39-50. DOI: 10.1107/S2052520615019538 305 40 http://doi.org/10.1107/S2052520615019538 234 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 14 Associated Article Eccles, Kevin S.; Stokes, Stephen P.; Daly, Carla A.; Barry, Nicola M.; McSweeney, Sharon P.; O'Neill, Damian J.; Kelly, Dawn M.; Jennings, W. Brian; Ní Dhubhghaill, O. M.; Moynihan, Humphrey A.; Maguire, Anita R.; Lawrence, Simon E.. Evaluation of the Bruker SMART X2S: crystallography for the nonspecialist?. Journal of Applied Crystallography 2011;44(1):213-215. DOI: 10.1107/S0021889810042561 371 40 http://doi.org/10.1107/S0021889810042561 15 Associated Article van Genderen, E.; Clabbers, M. T. B.; Das, P. P.; Stewart, A.; Nederlof, I.; Barentsen, K. C.; Portillo, Q.; Pannu, N. S.; Nicolopoulos, S.; Gruene, T.; Abrahams, J. P.. Ab initio structure determination of nanocrystals of organic pharmaceutical compounds by electron diffraction at room temperature using a Timepix quantum area direct electron detector. Acta Crystallographica Section A 2016;72(2):236-242. DOI: 10.1107/S2053273315022500 170 9 Italics 413 40 http://doi.org/10.1107/S2053273315022500 16 Associated Article van Genderen, E.; Clabbers, M. T. B.; Das, P. P.; Stewart, A.; Nederlof, I.; Barentsen, K. C.; Portillo, Q.; Pannu, N. S.; Nicolopoulos, S.; Gruene, T.; Abrahams, J. P.. Ab initio structure determination of nanocrystals of organic pharmaceutical compounds by electron diffraction at room temperature using a Timepix quantum area direct electron detector. Acta Crystallographica Section A 2016;72(2):236-242. DOI: 10.1107/S2053273315022500 170 9 Italics 413 40 http://doi.org/10.1107/S2053273315022500 17 Associated Article Childs, Scott L.; Wood, Peter A.; Rodríguez-Hornedo, Naír; Reddy, L. Sreenivas; Hardcastle, Kenneth I.. Analysis of 50 Crystal Structures Containing Carbamazepine Using theMaterialsModule ofMercury CSD. Crystal Growth & Design 2009;9(4):1869-. DOI: 10.1021/cg801056c 249 32 http://doi.org/10.1021/cg801056c 149 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 18 Associated Article Childs, Scott L.; Wood, Peter A.; Rodríguez-Hornedo, Naír; Reddy, L. Sreenivas; Hardcastle, Kenneth I.. Analysis of 50 Crystal Structures Containing Carbamazepine Using theMaterialsModule ofMercury CSD. Crystal Growth & Design 2009;9(4):1869-. DOI: 10.1021/cg801056c 249 32 http://doi.org/10.1021/cg801056c 149 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 19 Associated Article Childs, Scott L.; Wood, Peter A.; Rodríguez-Hornedo, Naír; Reddy, L. Sreenivas; Hardcastle, Kenneth I.. Analysis of 50 Crystal Structures Containing Carbamazepine Using theMaterialsModule ofMercury CSD. Crystal Growth & Design 2009;9(4):1869-. DOI: 10.1021/cg801056c 249 32 http://doi.org/10.1021/cg801056c 149 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 20 Associated Article Childs, Scott L.; Wood, Peter A.; Rodríguez-Hornedo, Naír; Reddy, L. Sreenivas; Hardcastle, Kenneth I.. Analysis of 50 Crystal Structures Containing Carbamazepine Using theMaterialsModule ofMercury CSD. Crystal Growth & Design 2009;9(4):1869-. DOI: 10.1021/cg801056c 249 32 http://doi.org/10.1021/cg801056c 149 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 21 Associated Article El Hassan, Nouha; Ikni, Aziza; Gillet, Jean-Michel; Spasojevic-de Biré, Anne; Ghermani, Nour Eddine. Electron Properties of Carbamazepine Drug in Form III. Crystal Growth & Design 2013;13(7):2887-. DOI: 10.1021/cg4002994 203 32 http://doi.org/10.1021/cg4002994 124 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 22 Associated Article El Hassan, Nouha; Ikni, Aziza; Gillet, Jean-Michel; Spasojevic-de Biré, Anne; Ghermani, Nour Eddine. Electron Properties of Carbamazepine Drug in Form III. Crystal Growth & Design 2013;13(7):2887-. DOI: 10.1021/cg4002994 203 32 http://doi.org/10.1021/cg4002994 124 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 23 Associated Article El Hassan, Nouha; Ikni, Aziza; Gillet, Jean-Michel; Spasojevic-de Biré, Anne; Ghermani, Nour Eddine. Electron Properties of Carbamazepine Drug in Form III. Crystal Growth & Design 2013;13(7):2887-. DOI: 10.1021/cg4002994 203 32 http://doi.org/10.1021/cg4002994 124 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 24 Associated Article Jean-Baptiste Arlin; Louise S. Price; Sarah L. Price; Alastair J. Florence. A strategy for producing predicted polymorphs: catemeric carbamazepine form V. Chem.Commun. 2011;47:7074-. DOI: 10.1039/c1cc11634g 188 33 http://doi.org/10.1039/c1cc11634g 133 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 25 Associated Article Nievergelt, Philipp P.; Spingler, Bernhard. Growing single crystals of small molecules by thermal recrystallization, a viable option even for minute amounts of material?. CrystEngComm 2017;19(1):142-. DOI: 10.1039/C6CE02222G 206 33 http://doi.org/10.1039/C6CE02222G 180 Associated Article doi:10.1002/jps.10455 http://doi.org/10.1002/jps.10455 DOI:10.1002/jps.10455 181 Associated Article doi:10.1002/jps.10093 http://doi.org/10.1002/jps.10093 DOI:10.1002/jps.10093 182 Associated Article doi:10.1039/b610317k http://doi.org/10.1039/b610317k DOI:10.1039/b610317k 183 Associated Article doi:10.1002/jps.20942 http://doi.org/10.1002/jps.20942 DOI:10.1002/jps.20942 184 Associated Article doi:10.1039/c1cc11634g http://doi.org/10.1039/c1cc11634g DOI:10.1039/c1cc11634g 185 Associated Article doi:10.1107/S0021889810042561 http://doi.org/10.1107/S0021889810042561 DOI:10.1107/S0021889810042561 186 Associated Article doi:10.1021/cg4002994 http://doi.org/10.1021/cg4002994 DOI:10.1021/cg4002994 187 Associated Article doi:10.1021/cg4002994 http://doi.org/10.1021/cg4002994 DOI:10.1021/cg4002994 188 Associated Article doi:10.1021/cg4002994 http://doi.org/10.1021/cg4002994 DOI:10.1021/cg4002994

Crystal Structure Data Information about this crystal structure record. 13 Crystal Structure Depiction https://www.crystallography.net/cod/2107460.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30618783_1 image/png 13 Hermann-Mauguin space group symbol P 1 21/n 1 13 Hall space group symbol -P 2yn 13 Space group number 14 13 a 7.4980 Å 13 b 11.058 Å 13 c 13.789 Å 13 α 90 ° 13 β 92.838 ° 13 γ 90 ° 13 Z 4 13 Z' 1 13 Residual factor 0.0679 14 Crystal Structure Depiction https://www.crystallography.net/cod/2300327.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30655266_1 image/png 14 Hermann-Mauguin space group symbol P 1 21/n 1 14 Hall space group symbol -P 2yn 14 Space group number 14 14 a 7.5500 Å 14 b 11.186 Å 14 c 13.954 Å 14 α 90.00 ° 14 β 92.938 ° 14 γ 90.00 ° 14 Z 4 14 Z' 1 14 Residual factor 0.0594 15 Crystal Structure Depiction https://www.crystallography.net/cod/2311081.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30655626_1 image/png 15 Hermann-Mauguin space group symbol P 1 21/n 1 15 Hall space group symbol -P 2yn 15 Space group number 14 15 a 7.578 Å 15 b 11.176 Å 15 c 13.991 Å 15 α 90 ° 15 β 93.08 ° 15 γ 90 ° 15 Z 4 15 Z' 1 15 Residual factor 0.2803 16 Crystal Structure Depiction https://www.crystallography.net/cod/2311083.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30655628_1 image/png 16 Hermann-Mauguin space group symbol P 1 21/n 1 16 Hall space group symbol -P 2yn 16 Space group number 14 16 a 7.576 Å 16 b 11.188 Å 16 c 13.967 Å 16 α 90 ° 16 β 87.03 ° 16 γ 90 ° 16 Z 4 16 Z' 1 16 Residual factor 0.4316 17 Crystal Structure Depiction https://www.crystallography.net/cod/4509215.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30729906_1 image/png 17 Hermann-Mauguin space group symbol C 1 2/c 1 17 Hall space group symbol -C 2yc 17 Space group number 15 17 a 20.4438 Å 17 b 5.1527 Å 17 c 26.5197 Å 17 α 90.00 ° 17 β 95.264 ° 17 γ 90.00 ° 17 Z 8 17 Z' 1 17 Residual factor 0.0460 18 Crystal Structure Depiction https://www.crystallography.net/cod/4509220.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30729910_1 image/png 18 Hermann-Mauguin space group symbol P 1 21/c 1 18 Hall space group symbol -P 2ybc 18 Space group number 14 18 a 10.3006 Å 18 b 26.972 Å 18 c 5.0718 Å 18 α 90.00 ° 18 β 104.235 ° 18 γ 90.00 ° 18 Z 4 18 Z' 1 18 Residual factor 0.0507 19 Crystal Structure Depiction https://www.crystallography.net/cod/4509221.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30729911_1 image/png 19 Hermann-Mauguin space group symbol P 1 21/c 1 19 Hall space group symbol -P 2ybc 19 Space group number 14 19 a 10.4207 Å 19 b 26.168 Å 19 c 5.2089 Å 19 α 90.00 ° 19 β 104.346 ° 19 γ 90.00 ° 19 Z 4 19 Z' 1 19 Residual factor 0.1169 20 Crystal Structure Depiction https://www.crystallography.net/cod/4509222.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30729912_1 image/png 20 Hermann-Mauguin space group symbol P 1 21/c 1 20 Hall space group symbol -P 2ybc 20 Space group number 14 20 a 10.330 Å 20 b 26.24 Å 20 c 5.110 Å 20 α 90.00 ° 20 β 104.21 ° 20 γ 90.00 ° 20 Z 4 20 Z' 1 20 Residual factor 0.3254 21 Crystal Structure Depiction https://www.crystallography.net/cod/4510731.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30730464_1 image/png 21 Hermann-Mauguin space group symbol P 1 21/n 1 21 Hall space group symbol -P 2yn 21 Space group number 14 21 a 7.487 Å 21 b 11.041 Å 21 c 13.775 Å 21 α 90.0 ° 21 β 92.9 ° 21 γ 90.0 ° 21 Z 4 21 Z' 1 22 Crystal Structure Depiction https://www.crystallography.net/cod/4510732.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30730465_1 image/png 22 Hermann-Mauguin space group symbol P 1 21/n 1 22 Hall space group symbol -P 2yn 22 Space group number 14 22 a 7.4874 Å 22 b 11.0406 Å 22 c 13.7754 Å 22 α 90 ° 22 β 92.9390 ° 22 γ 90 ° 22 Z 4 22 Z' 1 22 Residual factor 0.0364 23 Crystal Structure Depiction https://www.crystallography.net/cod/4510733.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30730466_1 image/png 23 Hermann-Mauguin space group symbol P 1 21/n 1 23 Hall space group symbol -P 2yn 23 Space group number 14 23 a 7.4874 Å 23 b 11.0406 Å 23 c 13.7754 Å 23 α 90 ° 23 β 92.9390 ° 23 γ 90 ° 23 Z 4 23 Z' 1 23 Residual factor 0.0114 24 Crystal Structure Depiction https://www.crystallography.net/cod/7106548.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30768396_1 image/png 24 Hermann-Mauguin space group symbol P b c a 24 Hall space group symbol -P 2ac 2ab 24 Space group number 61 24 a 9.1245 Å 24 b 10.4518 Å 24 c 24.8224 Å 24 α 90.00 ° 24 β 90.00 ° 24 γ 90.00 ° 24 Z 8 24 Z' 1 24 Residual factor 0.0872 25 Crystal Structure Depiction https://www.crystallography.net/cod/7227180.html https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/30796710_1 image/png 25 Hermann-Mauguin space group symbol P 1 21/n 1 25 Hall space group symbol -P 2yn 25 Space group number 14 25 a 7.49441 Å 25 b 11.06430 Å 25 c 13.80360 Å 25 α 90 ° 25 β 92.9142 ° 25 γ 90 ° 25 Z 4 25 Z' 1 25 Residual factor 0.0549 180 Crystal Structure Data doi:10.5517/cc67gd8 http://doi.org/10.5517/cc67gd8 DOI:10.5517/cc67gd8 180 Crystal Structure Depiction http://doi.org/10.5517/cc67gd8 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3319280_1 image/png 181 Crystal Structure Data doi:10.5517/cc8d2d3 http://doi.org/10.5517/cc8d2d3 DOI:10.5517/cc8d2d3 181 Crystal Structure Depiction http://doi.org/10.5517/cc8d2d3 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3331437_1 image/png 182 Crystal Structure Data doi:10.5517/ccnfx43 http://doi.org/10.5517/ccnfx43 DOI:10.5517/ccnfx43 182 Crystal Structure Depiction http://doi.org/10.5517/ccnfx43 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3342954_1 image/png 183 Crystal Structure Data doi:10.5517/ccpbnd1 http://doi.org/10.5517/ccpbnd1 DOI:10.5517/ccpbnd1 183 Crystal Structure Depiction http://doi.org/10.5517/ccpbnd1 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3348366_1 image/png 184 Crystal Structure Data doi:10.5517/ccvkx4f http://doi.org/10.5517/ccvkx4f DOI:10.5517/ccvkx4f 184 Crystal Structure Depiction http://doi.org/10.5517/ccvkx4f https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3378436_1 image/png 185 Crystal Structure Data doi:10.5517/ccwb9q6 http://doi.org/10.5517/ccwb9q6 DOI:10.5517/ccwb9q6 185 Crystal Structure Depiction http://doi.org/10.5517/ccwb9q6 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3382620_1 image/png 186 Crystal Structure Data doi:10.5517/cc1178yh http://doi.org/10.5517/cc1178yh DOI:10.5517/cc1178yh 186 Crystal Structure Depiction http://doi.org/10.5517/cc1178yh https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3407123_1 image/png 187 Crystal Structure Data doi:10.5517/cc1178zj http://doi.org/10.5517/cc1178zj DOI:10.5517/cc1178zj 187 Crystal Structure Depiction http://doi.org/10.5517/cc1178zj https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3407124_1 image/png 188 Crystal Structure Data doi:10.5517/cc11790l http://doi.org/10.5517/cc11790l DOI:10.5517/cc11790l 188 Crystal Structure Depiction http://doi.org/10.5517/cc11790l https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/3407125_1 image/png

Chemical Safety Link to the Safety and Hazard section of this page and link to the Laboratory Chemical Safety Summary (LCSS) datasheet for this compound. true true 199 Chemical Safety 0 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS07.svg Icon Irritant 1 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS08.svg Icon Health Hazard

Names and Identifiers Chemical names, synonyms, identifiers, and descriptors.

Record Description Summary Information true true 7 Record Description Ontology Summary Carbamazepine is a dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant. It has a role as an anticonvulsant, an EC 3.5.1.98 (histone deacetylase) inhibitor, a mitogen, a glutamate transporter activator, an antimanic drug, an analgesic, a non-narcotic analgesic, an environmental contaminant, a xenobiotic, a drug allergen and a sodium channel blocker. It is a dibenzoazepine and a member of ureas. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 19 14 https://pubchem.ncbi.nlm.nih.gov/compound/dibenzoazepine PubChem Internal Link CID-3964 42 22 https://pubchem.ncbi.nlm.nih.gov/compound/5H-dibenzo%5Bb%2Cf%5Dazepine PubChem Internal Link CID-9212 247 9 https://pubchem.ncbi.nlm.nih.gov/compound/glutamate PubChem Internal Link CID-4525487 405 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 437 14 https://pubchem.ncbi.nlm.nih.gov/compound/dibenzoazepine PubChem Internal Link CID-3964 30 Carbamazepine, also known as Tegretol, is an anticonvulsant drug and analgesic drug used to control seizures and to treat pain resulting from trigeminal neuralgia. It was initially approved by the FDA in 1965. Aside from the above uses, this drug is also given to control the symptoms of bipolar 1. Interestingly, carbamazepine was the first anticonvulsant used to treat individuals with bipolar disorder. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 29 8 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol PubChem Internal Link CID-2554 314 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 58 FDA Pharmacology Summary Carbamazepine is a Mood Stabilizer. The mechanism of action of carbamazepine is as a Cytochrome P450 3A4 Inducer, and Cytochrome P450 1A2 Inducer, and Cytochrome P450 2B6 Inducer, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer. The physiologic effect of carbamazepine is by means of Decreased Central Nervous System Disorganized Electrical Activity. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 63 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 273 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 73 LiverTox Summary Carbamazepine is an aromatic anticonvulsant that is widely used in therapy of epilepsy and trigeminal neuralgia and is a well established cause of clinically apparent liver injury which can be severe and even fatal. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 146 Carbamazepine is a tricyclic compound chemically related to tricyclic antidepressants (TCA) with anticonvulsant and analgesic properties. Carbamazepine exerts its anticonvulsant activity by reducing polysynaptic responses and blocking post-tetanic potentiation. Its analgesic activity is not understood; however, carbamazepine is commonly used to treat pain associated with trigeminal neuralgia. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 87 3 https://pubchem.ncbi.nlm.nih.gov/compound/TCA PubChem Internal Link CID-6421 138 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 313 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 191 An anticonvulsant used to control grand mal and psychomotor or focal seizures. Its mode of action is not fully understood, but some of its actions resemble those of phenytoin; although there is little chemical resemblance between the two compounds, their three-dimensional structure is similar. 165 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 198 A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.

Computed Descriptors Structural descriptors generated or computed for the structures of this compound, including the IUPAC name, InChI/InChIKey, and canonical/isomeric SMILES.

IUPAC Name Chemical name of this compound, computed from its structure based on the International Union of Pure and Applied Chemistry (IUPAC) nomenclature standards. https://iupac.org/what-we-do/nomenclature/ 199 Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14) benzo[b][1]benzazepine-11-carboxamide

InChI The International Chemical Identifier (InChI) is a computed, non-proprietary identifier for a chemical structure. The InChI is an International Union of Pure and Applied Chemistry (IUPAC) standard. https://iupac.org/who-we-are/divisions/division-details/inchi/ 199 Computed by InChI 1.0.6 (PubChem release 2021.10.14) InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

InChIKey An InChIKey is a 27-character hash code derived from an InChI. The International Chemical Identifier (InChI) is a computed, non-proprietary identifier for a chemical structure. The InChI is an International Union of Pure and Applied Chemistry (IUPAC) standard. https://iupac.org/who-we-are/divisions/division-details/inchi/ 199 Computed by InChI 1.0.6 (PubChem release 2021.10.14) FFGPTBGBLSHEPO-UHFFFAOYSA-N

Canonical SMILES The Simplified Molecular-Input Line-Entry System (SMILES) is a widely-used line notation for chemical structures. PubChem computes two kinds of SMILES strings for compounds: canonical SMILES (computed from chemical structures devoid of isotopic and stereochemical information), and isomeric SMILES (computed from chemical structures containing isotopic and stereochemical information). This section shows the canonical SMILES of the compound. https://www.daylight.com/dayhtml/doc/theory/theory.smiles.html 199 Computed by OEChem 2.3.0 (PubChem release 2021.10.14) C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N

Molecular Formula A chemical formula is a way of expressing information about the proportions of atoms that constitute a particular chemical compound, using a single line of chemical element symbols and numbers. PubChem uses the Hill system, whereby the number of carbon atoms in a molecule is indicated first, the number of hydrogen atoms second, and then the number of all other chemical elements in alphabetical order. When the formula contains no carbon, all the elements, including hydrogen, are listed alphabetically. Sources other than PubChem may include a variant of the formula that is more structural or natural to chemists, for example, H2SO4 for sulfuric acid, rather than the Hill version H2O4S. https://pubs.acs.org/doi/abs/10.1021/ja02046a005 true 195 Molecular Formula C15H12N2O 199 Computed by PubChem 2.2 (PubChem release 2021.10.14) C15H12N2O

Other Identifiers Other identifiers assigned to this chemical.

CAS A CAS Registry Number (also called CAS RN or CAS Number) is a proprietary registry number assigned by the Chemical Abstracts Service (CAS) division of the American Chemical Society (ACS). It is a numeric identifier that can contain up to 10 digits, divided by hyphens into three parts. https://www.cas.org/support/documentation/chemical-substances/faqs 2 https://commonchemistry.cas.org/detail?cas_rn=298-46-4 298-46-4 9 298-46-4 30 298-46-4 43 CAS 298-46-4 44 CAS 298-46-4 46 298-46-4 49 298-46-4 50 298-46-4 59 298-46-4 60 298-46-4 147 298-46-4

Related CAS The Chemical Abstract Service (CAS) registry numbers for related chemicals (e.g., parents, components, mixtures, salt forms, etc.) 3 9 85756-57-6 (di-hydrate)

European Community (EC) Number The European Community (EC) number is a seven-digit identifier assigned by the European Chemicals Agency (ECHA) to substances for regulatory purposes within the European Union. EC numbers are sometimes referred to as EINECS, ELINCS, or NLP numbers, because the EC Inventory comprises three individual inventories (EINECS, ELINCS, and the NLP list). https://echa.europa.eu/information-on-chemicals/ec-inventory 49 https://echa.europa.eu/substance-information/-/substanceinfo/100.005.512 206-062-7

UNII UNique Ingredient Identifier (UNII) code for this chemical. It is a non-proprietary registry number assigned by the U.S. Food and Drug Administration (FDA). https://www.fda.gov/industry/fda-data-standards-advisory-board/fdas-global-substance-registration-system 50 https://gsrs.ncats.nih.gov/ginas/app/beta/substances/33CM23913M 33CM23913M

ChEBI ID Identifier from database and ontology of molecular entities focused on 'small' chemical compounds used by the Chemical Entities of Biological Interest (ChEBI) https://www.ebi.ac.uk/chebi/ 7 https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3387 CHEBI:3387

ChEMBL ID ChEMBL compound identifier https://www.ebi.ac.uk/chembl/ 8 https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL108/ CHEMBL108

DrugBank ID Drug identifier used by the DrugBank database https://go.drugbank.com/ 30 https://www.drugbank.ca/drugs/DB00564 DB00564

DSSTox Substance ID Substance identifier used in the Distributed Structure-Searchable Toxicity (DSSTox) Database. https://www.epa.gov/chemical-research/distributed-structure-searchable-toxicity-dsstox-database 46 https://comptox.epa.gov/dashboard/DTXSID4022731 DTXSID4022731

HMDB ID A chemical substance identifier from the HMDB database https://hmdb.ca/ 60 https://hmdb.ca/metabolites/HMDB0014704 HMDB0014704

KEGG ID KEGG compound/drug identifier https://www.kegg.jp/ 70 https://www.kegg.jp/entry/C06868 C06868 71 https://www.kegg.jp/entry/D00252 D00252

Metabolomics Workbench ID Registration number used by Metabolomics Workbench https://www.metabolomicsworkbench.org/ 139 https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=42899 42899

NCI Thesaurus Code Stable, unique code for biomedical concept https://ncithesaurus.nci.nih.gov 146 https://ncithesaurus.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=ncit&code=C341 C341

Nikkaji Number Substance identifier used in the Japan Chemical Substance Dictionary (Nikkaji). https://jglobal.jst.go.jp/en/ 69 http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J8.590A J8.590A

NSC Number The National Service Center (NSC) number is a numeric identifier for substances submitted to the National Cancer Institute (NCI) for testing and evaluation. It is a registration number for the Developmental Therapeutics Program (DTP) repository. https://dtp.cancer.gov/organization/dscb/compoundSubmission/faqs.htm 3 43 NSC Number https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=755920 755920 44 NSC Number https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=169864 169864

Pharos Ligand ID Ligand identifier used by Pharos https://pharos.nih.gov/ 164 https://pharos.nih.gov/ligands/7U7WXCCPXPYL 7U7WXCCPXPYL

RXCUI RxNorm concept unique identifier (RXCUI) https://www.nlm.nih.gov/research/umls/rxnorm/index.html 162 https://rxnav.nlm.nih.gov/id/rxnorm/2002 2002

Wikidata Wikidata entity identifier for the given compound. https://www.wikidata.org/w/index.php?title=Special:WhatLinksHere/Property:P662 194 https://www.wikidata.org/wiki/Q410412 Q410412

Wikipedia Wikidata entity identifier for this compound. 195 https://en.wikipedia.org/wiki/Carbamazepine Carbamazepine 196 https://en.wikipedia.org/wiki/Carbamazepine Carbamazepine

Synonyms Alternative names for this PubChem Compound record. A compound can have many different names. For example, acetone (CH3C(=O)CH3) is also known as propanone, propan-2-one, or dimethyl ketone. The brand name of a product is commonly used to indicate the primary chemical ingredient(s) in the product (e.g., Tylenol, a common pain killer, is often used for acetaminophen, its active ingredient). Another example of common synonyms is record identifiers used in different data collections, such as Chemical Abstract Service (CAS) registry numbers, FDA UNII (Unique Ingredient Identifiers), and many others. All these various names and identifiers that designate this compound are organized under the Synonyms section.

MeSH Entry Terms Medical Subject Heading (MeSH) names or identifiers matching this PubChem Compound record. The matching between the MeSH and compound records is performed by name matching (i.e., identical common names), as described in Kim et al., J. Cheminform., 2016, 8, 32. http://doi.org/10.1186/s13321-016-0142-6 Columns 198 Amizepine Carbamazepine Carbamazepine Acetate Carbamazepine Anhydrous Carbamazepine Dihydrate Carbamazepine Hydrochloride Carbamazepine L-Tartrate (4:1) Carbamazepine Phosphate Carbamazepine Sulfate (2:1) Carbazepin Epitol Finlepsin Neurotol Tegretol

Depositor-Supplied Synonyms Chemical names provided by individual data contributors. Synonyms of Substances corresponding to a PubChem Compound record are combined. Some contributed names may be considered erroneous and filtered out. The link on each synonym shows which depositors provided that particular synonym for this structure. Columns true 199 carbamazepine 298-46-4 Tegretol Carbamazepen Biston Finlepsin Equetro Tegretal 5H-Dibenzo[b,f]azepine-5-carboxamide 5H-Dibenz[b,f]azepine-5-carboxamide Carbazepine Timonil Carbamezepine Karbamazepin Carbatrol Neurotol Stazepine Telesmin Epitol Lexin Tegretol-Xr Carbamazepinum Carbamazepin Teril Geigy 32883 Carbamazepina Amizepin Bipotrol Carnexiv Sirtal benzo[b][1]benzazepine-11-carboxamide 5H-Dibenz(b,f)azepine-5-carboxamide 5-Carbamyl-5H-dibenzo(b,f)azepine 5-Carbamoyl-5H-dibenzo(b,f)azepine Calepsin 5-Carbamoyl-5H-dibenz(b,f)azepine Karbelex Neurotop G-32883 Carbamazepine Anhydrous 5-Carbamoyl-5H-dibenz[b,f]azepine G 32883 NSC 169864 CHEBI:3387 HSDB 3019 Carbatrol extended-release Carbamazepinum [INN-Latin] EINECS 206-062-7 MFCD00005073 Carbamazepina [INN-Spanish] Carbamazepine extended release 5-Carbamyldibenzo(b,f)azepine NSC-169864 BRN 1246090 5-Carbamoyldibenzo(b,f)azepine DTXSID4022731 UNII-33CM23913M NSC169864 CHEMBL108 33CM23913M MLS000069652 DTXCID902731 CBZ NCGC00015234-11 Carbamazepine [USAN:USP:INN:BAN:JAN] CAS-298-46-4 SMR000058201 Stazepin Carbamazepinum (INN-Latin) Carbamazepina (INN-Spanish) CARBAMAZEPINE (MART.) CARBAMAZEPINE [MART.] CARBAMAZEPINE (USP-RS) CARBAMAZEPINE [USP-RS] 5H-dibenzo[b,f]azepine-5-carboxamide;Oxcarbazepine IMpurity A Carbelan CARBAMAZEPINE (EP MONOGRAPH) CARBAMAZEPINE (USP IMPURITY) CARBAMAZEPINE [EP MONOGRAPH] CARBAMAZEPINE [USP IMPURITY] CARBAMAZEPINE (USP MONOGRAPH) CARBAMAZEPINE [USP MONOGRAPH] Tegretol Cr 5H-dibenzo(b,f)azepine-5-carboxamide Carbamazepine (USAN:USP:INN:BAN:JAN) SMR001227191 OXCARBAZEPINE IMPURITY A (EP IMPURITY) OXCARBAZEPINE IMPURITY A [EP IMPURITY] SR-01000000229 Carbmazepine Trimonil CarbamazepineER Neurotop retard TegretolXR Carbamazepine ER dibenzo[b,f]azepine-5-carboxamide Tegretol (TN) N6W Prestwick_104 Equetro (TN) Carbamazepine, powder Opera_ID_72 Spectrum_000096 Prestwick0_000052 Prestwick1_000052 Prestwick2_000052 Prestwick3_000052 Spectrum2_000125 Spectrum3_000325 Spectrum4_000262 Spectrum5_000936 Carbamazepine (Carbatrol) Lopac-C-4024 ChemDiv1_018966 CARBAMAZEPINE [MI] CBChromo1_000350 Epitope ID:174842 Iminostilbene-N-carboxamide CARBAMAZEPINE [INN] CARBAMAZEPINE [JAN] CARBAMAZEPINE [HSDB] CARBAMAZEPINE [USAN] Lopac0_000292 Oprea1_790775 SCHEMBL21639 BSPBio_000203 BSPBio_001929 CARBAMAZEPINE [VANDF] KBioGR_000724 KBioSS_000516 MLS001055475 MLS001074172 MLS002548877 BIDD:GT0479 DivK1c_000388 DivK1c_003750 SPECTRUM1500159 SPBio_000170 SPBio_002124 CARBAMAZEPINE [WHO-DD] CARBAMAZEPINE [WHO-IP] BPBio1_000225 GTPL5339 SCHEMBL19838283 HMS501D10 HMS640O02 KBio1_000388 KBio2_000516 KBio2_003084 KBio2_005652 KBio3_001149 WLN: T C676 BNJ BVZ Carbamazepine (JP17/USP/INN) CBZ;NSC 169864 N03AF01 SPD-417 Carbamazepine, analytical standard NINDS_000388 Carbamazepine, 1mg/ml in Methanol HMS1568K05 HMS1920I17 HMS2090M07 HMS2091O19 HMS2095K05 HMS2233G16 HMS3039K09 HMS3259B21 HMS3260L06 HMS3372J13 HMS3657G03 HMS3712K05 HMS3747E03 Pharmakon1600-01500159 CARBAMAZEPINE [ORANGE BOOK] BCP21380 HY-B0246 5-Carbomoyl-5H-dibenzo(b,f)azepine Tox21_110104 Tox21_202273 Tox21_300195 Tox21_500292 AC2074 BDBM50003659 CCG-38931 NSC755920 s1693 STK177357 STL453548 11-benzo[b][1]benzazepinecarboxamide 5H-Dibenz[b,f]azepine-5-carboxamine 5H-Dibenzo(b,f)azepin-5-carboxamide Carbamazepine 1.0 mg/ml in Methanol CARBAMAZEPINUM [WHO-IP LATIN] AKOS003235644 AKOS025397243 Tox21_110104_1 AC-9538 DB00564 KS-5146 LP00292 NC00679 NSC-755920 SDCCGSBI-0050280.P005 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide CDS1_002710 IDI1_000388 5H-Dibenzo[b,f]azepine-5-carboxamide # NCGC00015234-01 NCGC00015234-02 NCGC00015234-03 NCGC00015234-04 NCGC00015234-05 NCGC00015234-06 NCGC00015234-07 NCGC00015234-08 NCGC00015234-09 NCGC00015234-10 NCGC00015234-12 NCGC00015234-13 NCGC00015234-14 NCGC00015234-15 NCGC00015234-16 NCGC00015234-18 NCGC00015234-19 NCGC00015234-33 NCGC00023877-03 NCGC00023877-04 NCGC00023877-05 NCGC00023877-06 NCGC00023877-07 NCGC00023877-08 NCGC00253982-01 NCGC00259822-01 NCGC00260977-01 BC166161 SY002823 (z)-5h-dibenzo[b,f]azepine-5-carboxamide SBI-0050280.P004 5H-dibenzo[b,f]azepine-5-carboximidic acid DB-047659 Dibenzo[b,f]azepine-5-carboxylic acid amide EU-0100292 NS00000207 SW220141-1 EN300-21678 BIM-0050280.0001 C 4024 C06868 Carbamazepine, meets USP testing specifications D00252 5H-Dibenz(b,f)azepine-5-carboxamide maleic acid 5H-Dibenz(b,f)azepine-5-carboxamide oxalic acid AB00051931-17 AB00051931-18 AB00051931_19 AB00051931_20 A820074 Q410412 carbamazepine host structure with maleic acid removed carbamazepine host structure with oxalic acid removed Q-200792 SR-01000000229-2 SR-01000000229-4 SR-01000000229-7 5H-Dibenz(b,f)azepine-5-carboxamide DL-tartaric acid BRD-K71799949-001-06-7 F0348-2551 Z104508594 carbamazepine host structure with DL-tartaric acid removed Dibenzo[b,f]azepine-5-carboxylic acid amide(Carbamazepine) carbamazepine host structure with 4-hydroxybenzoic acid removed Carbamazepine, British Pharmacopoeia (BP) Reference Standard Carbamazepine, European Pharmacopoeia (EP) Reference Standard Carbamazepine, United States Pharmacopeia (USP) Reference Standard 2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide Carbamazepine, Pharmaceutical Secondary Standard; Certified Reference Material

Removed Synonyms Potentially erroneous chemical names and identifiers provided by PubChem Substance records for the same chemical structure that were removed by name/structure consistency filtering. true 199 Carbamazepan Carbazepin Amizepine captopril Atretol Carbamazepine-D10 Novo-Carbamaz Nu-Carbamazepine Tegretol XR Apo-Carbamazepine Tegretol Chewtabs Taro-Carbamazepine Carbamazepine dihydrate Carbamazepine Phosphate carbamazepine hydrate carbamazepine sulfate Carbamazepine Acetate carbamazepine tartrate Carbamazepine-d2 (Major) Taro-Carbamazepine Cr Carbamazepine Hydrochloride carbamazepine (Tegretol) AC1L1DXT AC1Q4ZSU AC1Q4ZSV C15H12N2O FFGPTBGBLSHEPO-UHFFFAOYSA-N D04MSM Carbamazepine (iv, epilepsy) Carbamazepine Sulfate (2:1) CARBAMAZEPINE, U.S.P. ZINC4785 ERK5-1O15 AOB5783 Carbamazepine [USAN:INN:BAN:JAN] Carbamazepine L-Tartrate (4:1) CID2554 ACT02606 KS-00000KI8 c1095 C15-H12-N2-O Carbamazepine [USAN:BAN:INN:JAN] 5H-Dibenz[b,f]azepine-5- carboxamide AN-6325 Carbamazepine (iv, epilepsy), Lundbeck Carbamazepine, 98% - 100G 100g CS-2225 5H-Dibenz[ b, f]azepine-5-carboxamide 5H-Dibenz[b,f]-nu-azepine-5-carboxamide AJ-08227 AJ-08230 AK116064 BC200975 CPD001227191 H495 LS-60362 SAM002264603 SC-16243 ST075773 ZB000594 AB0070254 AB1009530 ST2418853 B1390 FT-0602927 FT-0696814 H2605 5-20-08-00247 (Beilstein Handbook Reference) A10179 Carbamazepine (<lt/> 100 microg/ml) in methanol D002220 I06-0863 5,6-dideuteriobenzo[b][1]benzazepine-11-carboxamide Carbamazepine (iv, epilepsy), Ovation Pharmaceuticals 5H-Dibenzo[b,f]azepine-5-(~13~C,~15~N)carboxamide Carbamazepine, 97%, a sodium channel blocker - 1g 1g 5H-Dibenz(b,f)azepine-5-carboxamide 4-hydroxybenzoic acid 1189902-21-3 Carbamazepine solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material 1173022-00-8 132183-78-9 5H-Dibenzo[b,f]azepine-5-carboxamide; Carbamazepine; Oxcarbazepine Imp. A (EP); 5-Carbamoyl-5H-dibenz[b,f]azepine; Amizepin; Biston; CBZ; Calepsin; Carbamazepen; Carbamazepin; Carbatrol; Carbazepine; Carbelan; Epitol; Finlepsin; G 32883; Geigy 32883; Karbamazepin; Karbelex; Karberol; NSC 169864; Neurotol; Neurotop; Sirtal; Stazepine; Tegretal; Tegretol; Tegretol XR; Telesmin; Timonil; Oxcarbazepine Impurity A 63918-70-7 Azapentacene; Sodium 5,12-dihydroazapentacene disulfonate; 5,12-Dihydroquinoxalino[2,3-b]phenazine sulfonate sodium salt

Create Date Date when this compound record was created. For more information on various dates for PubChem records, visit the PubChem Record Dates help page. https://pubchem.ncbi.nlm.nih.gov/docs/record-dates true true 199 2005-03-25

Modify Date Date when this compound record was last modified. For more information on various dates for PubChem records, visit the PubChem Record Dates help page. https://pubchem.ncbi.nlm.nih.gov/docs/record-dates true true 199 2024-05-03

Chemical and Physical Properties Various chemical and physical properties that are experimentally determined for this compound. See also the Safety and Hazard Properties section (if available), which has additional properties pertinent to chemical safety and hazards.

Computed Properties Properties of this compound computed from its molecular formula and structure. Subsections 3 Property Name Property Value Reference Name Value Reference

Molecular Weight Molecular weight or molecular mass refers to the mass of a molecule. It is calculated as the sum of the mass of each constituent atom multiplied by the number of atoms of that element in the molecular formula. The molecular weight is also called the relative molar mass, because molecular weights are reported in daltons, which is defined relative to the mass of the isotope 12C (carbon 12). https://www.degruyter.com/document/doi/10.1515/pac-2017-1002/html?lang=en true 199 Computed by PubChem 2.2 (PubChem release 2021.10.14) 236.27 g/mol

XLogP3 XLogP3 is a predicted octanol-water partition coefficient, computed using the algorithm described in J. Chem. Inf. Model. 2007, 47, 6, 2140-2148. It is used as a measure of hydrophilicity or hydrophobicity of a molecule. https://pubmed.ncbi.nlm.nih.gov/17985865/ 199 Computed by XLogP3 3.0 (PubChem release 2021.10.14) 2.5

Hydrogen Bond Donor Count The number of hydrogen bond donors in this compound. 199 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 1

Hydrogen Bond Acceptor Count The number of hydrogen bond acceptors in this compound. 199 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 1

Rotatable Bond Count A rotatable bond is defined as any single-order non-ring bond, where atoms on either side of the bond are in turn bound to nonterminal heavy (i.e., non-hydrogen) atoms. That is, where rotation around the bond axis changes the overall shape of the molecule, and generates conformers which can be distinguished by standard fast spectroscopic methods. 199 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 0

Exact Mass The exact mass of an isotopic species is obtained by summing the masses of the individual isotopes of the molecule. 199 Computed by PubChem 2.2 (PubChem release 2021.10.14) 236.094963011 g/mol

Monoisotopic Mass The monoisotopic mass is the sum of the masses of the atoms in a molecule using the unbound, ground-state, rest mass of the principal (most abundant) isotope for each element instead of the isotopic average mass. 199 Computed by PubChem 2.2 (PubChem release 2021.10.14) 236.094963011 g/mol

Topological Polar Surface Area The topological polar surface area (TPSA) is an estimate of the polar surface area (in Angstroms^2) of a molecule, computed as the surface sum over polar atoms in the molecule. The implementation follows the paper by Ertl et al. [J. Med. Chem. 2000, 43, 3714-3717]: only N and O are considered, 3D coordinates are not used, and there are various precomputed factors for different hybridizations, charges and participation in aromatic systems. https://pubmed.ncbi.nlm.nih.gov/11020286/ 199 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 46.3 Å²

Heavy Atom Count The number of heavy atoms (i.e., non-hydrogen atoms) in this compound. 199 Computed by PubChem 18

Formal Charge Formal charge is the difference between the number of valence electrons of each atom and the number of electrons the atom is associated with. Formal charge assumes any shared electrons are equally shared between the two bonded atoms. 199 Computed by PubChem 0

Complexity The complexity rating of a compound is a rough estimate of how complicated a structure is, seen from both the point of view of the elements contained and the displayed structural features including symmetry. This complexity rating is computed using the Bertz/Hendrickson/Ihlenfeldt formula. https://pubchem.ncbi.nlm.nih.gov/docs/glossary#section=Complexity 199 Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14) 326

Isotope Atom Count Isotope atom count is the number of isotopes that are not most abundant for the corresponding chemical elements. Isotopes are variants of a chemical element which differ in neutron number. For example, among three isotopes of carbon (i.e., C-12, C-13, and C-14), the isotope atom count considers the C-13 and C-14 atoms, because C-12 is the most abundant isotope of carbon. 199 Computed by PubChem 0

Defined Atom Stereocenter Count An atom stereocenter, also known as a chiral center, is an atom that is attached to four different types of atoms (or groups of atoms) in the tetrahedral arrangement. It can have either (R)- or (S)- configurations. Some compounds, such as racemic mixtures, have an undefined atom stereocenter, whose (R/S)-configuration is not specifically defined. The "defined atom stereocenter count" is the number of atom stereocenters whose configurations are specifically defined. 199 Computed by PubChem 0

Undefined Atom Stereocenter Count The number of atom stereocenters whose configurations are not specifically defined. For the definition of atom stereocenters, see the "defined atom stereocenter count" above. 199 Computed by PubChem 0

Defined Bond Stereocenter Count A bond stereocenter is a non-rotatable bond around which two atoms can have different arrangement (as in cis- and trans-forms of butene around its double bond). Some compounds have an undefined bond stereocenter, whose stereochemistry is not specifically defined. The "defined bond stereocenter count" is the number of bond stereocenters whose configurations are specifically defined. 199 Computed by PubChem 0

Undefined Bond Stereocenter Count The number of bond stereocenters whose configurations are not specifically defined. For the definition of bond stereocenters, see the "defined bond stereocenter count" above. 199 Computed by PubChem 0

Covalently-Bonded Unit Count A covalently-bonded unit is a group of atoms connected by covalent bonds, ignoring other bond types (or a single atom without covalent bonds). The "covalently-bonded unit count" property is the number of such units in this compound compound. 199 Computed by PubChem 1

Compound Is Canonicalized Whether the compound has successfully passed PubChem's valence bond canonicalization procedure. Some large, complex, or highly symmetric structures may fail this process. 199 Computed by PubChem (release 2021.10.14) Yes

Experimental Properties Various experimentally determined properties for this compound. See also the Safety and Hazard Properties section (if available), which has additional properties pertinent to chemical safety and hazards.

Physical Description The appearance or features of this compound, including color, odor, state, taste and more in general. 60 Solid

Color/Form Color is the aspect of any object that may be described in terms of hue, lightness, and saturation. https://www.britannica.com/science/color 59 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 298 Crystals from absolute ethanol and benzene 23 7 https://pubchem.ncbi.nlm.nih.gov/compound/ethanol PubChem Internal Link CID-702 35 7 https://pubchem.ncbi.nlm.nih.gov/compound/benzene PubChem Internal Link CID-241 59 PEER REVIEWED Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3171 White to off-white powder

Boiling Point The temperature at which this compound changes state from liquid to gas at a given atmospheric pressure. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_Lab_Techniques_(Nichols)/06%3A_Miscellaneous_Techniques/6.02%3A_Boiling_Point 30 https://www.lookchem.com/Carbamazepine/ 399.6±45.0

Melting Point This section provides the melting point and/or freezing point. The melting point is the temperature at which a substance changes state from solid to liquid at atmospheric pressure. When considered as the temperature of the reverse change (from liquid to solid), it is referred to as the freezing point. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_Lab_Techniques_(Nichols)/06%3A_Miscellaneous_Techniques/6.01%3A_Melting_Point 30 https://www.lookchem.com/Carbamazepine/ 189-192 59 PEER REVIEWED Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-140 190.2 °C 60 190.2 °C

Solubility The solubility of a substance is the amount of that substance that will dissolve in a given amount of solvent. The default solvent is water, if not indicated. https://chem.libretexts.org/Courses/Purdue/Purdue%3A_Chem_26505%3A_Organic_Chemistry_I_(Lipton)/Chapter_4._Intermolecular_Forces_and_Physical_Properties/4.4_Solubility 1 >35.4 [ug/mL] (The mean of the results at pH 7.4) 59 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 298 Sol in alcohol, acetone, propylene glycol; practically insol in water 16 7 https://pubchem.ncbi.nlm.nih.gov/compound/acetone PubChem Internal Link CID-180 25 16 https://pubchem.ncbi.nlm.nih.gov/compound/propylene%20glycol PubChem Internal Link CID-1030 64 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 59 PEER REVIEWED Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA3 : 18 (1985) Soluble in chloroform, dimethylformamide, ethylene glycol monomethyl ether, or methanol; only slightly soluble in ethanol or glacial acetic acid 11 10 https://pubchem.ncbi.nlm.nih.gov/compound/chloroform PubChem Internal Link CID-6212 23 17 https://pubchem.ncbi.nlm.nih.gov/compound/dimethylformamide PubChem Internal Link CID-6228 42 32 https://pubchem.ncbi.nlm.nih.gov/compound/ethylene%20glycol%20monomethyl%20ether PubChem Internal Link CID-8019 79 8 https://pubchem.ncbi.nlm.nih.gov/compound/methanol PubChem Internal Link CID-887 114 7 https://pubchem.ncbi.nlm.nih.gov/compound/ethanol PubChem Internal Link CID-702 133 11 https://pubchem.ncbi.nlm.nih.gov/compound/acetic%20acid PubChem Internal Link CID-176 60 1.52e-01 g/L

LogP Log P is the partition coefficient expressed in logarithmic form. The partition coefficient is the ratio of concentrations of a compound in a mixture of two immiscible solvents at equilibrium. This ratio is therefore used to compare the solubilities of the solute in these two solvents. Because octanol and water are the most commonly used pair of solvents for measuring partition coefficients, the Log P values listed in this section refer to octanol/water partition coefficients, unless indicated otherwise. 30 http://www.t3db.ca/toxins/T3D2826 2.77 59 PEER REVIEWED Dal Pozzo A et al; Int J Pharm 50: 97-101 (1989) log Kow = 2.45 60 2.3

LogS The base-10 logarithm of the aqueous solubility of this compound. https://chem.libretexts.org/Courses/Purdue/Purdue%3A_Chem_26505%3A_Organic_Chemistry_I_(Lipton)/Chapter_4._Intermolecular_Forces_and_Physical_Properties/4.4_Solubility 30 http://www.t3db.ca/toxins/T3D2826 -3.2

Stability/Shelf Life Tendency of a material to resist change or decomposition due to internal reaction, or due to the action of air, heat, light, pressure, etc. See also the Stability and Reactivity subsection under the Safety and Hazards section on this page (when available). 59 PEER REVIEWED PMID:8027920 Matsuda Y et al; J Pharm Pharmacol 46: 162-7 (1994) To study the photostability of carbamazepine polymorphs, the pure materials on the tablet surface were evaluated without physical damage by means of Fourier-transform infrared reflection-absorption infrared spectrometry (FT-IR-RAS) and colorimetric measurement of the carbamazepine polymorphs I, II, and III, after photodegradation at 2 irradiation intensities under a near-UV fluorescent lamp. The surface of sample pellets of all crystalline forms turned gradually from white to yellow-orange upon exposure to light, and the discoloration rate of form II was faster than that of forms I and III, indicating that form II was the most unstable of the three. The semilogarithmic plots of the photodegradation profiles of the various polymorphs were straight lines, including the induction period, indicating that degradation of the drug on the surface followed first-order kinetics. The induction periods of all forms were not significantly different. However, the degradation rate constant of form II was 5.1 and 1.5 times larger than those of forms I and III, respectively. 31 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 268 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Ionization Efficiency The ratio of the number of ions formed to the number of electrons or photons used in an ionization process. https://goldbook.iupac.org/terms/view/I03196 ThisSection 2 Name Value CommaSeparated 72 Ionization mode Positive 72 logIE 2.4 72 pH 2.7 72 Instrument Agilent XCT 72 Ion source Electrospray ionization 72 Additive formic acid (5.3nM) 72 Organic modifier MeCN (80%) 72 Reference DOI: 4 1 https://doi.org/

Dissociation Constants A specific type of equilibrium constant that measures the propensity of a larger object to separate (dissociate) reversibly into smaller components, as when a complex falls apart into its component molecules, or when a salt splits up into its component ions. This includes pKa (the negative logarithm of the acid dissociation constant) and pKb (the negative logarithm of the base dissociation constant). 30 pKa http://www.t3db.ca/toxins/T3D2826 15.96, -3.8 59 PEER REVIEWED PMID:12448549 Jones OAH et al; Water Res 36: 5013-22 (2002) pKa = 13.9

Collision Cross Section Collision cross section (CCS) represents the effective area for the interaction between an individual ion and the neutral gas through which it is traveling (e.g., in ion mobility spectrometry (IMS) experiments). It quantifies the probability of a collision taking place between two or more particles. https://pubmed.ncbi.nlm.nih.gov/28035808/ 3 Ross et al. JASMS 2022, 33, 1061-1072. DOI:10.1021/jasms.2c00111 148.42 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] 15 1 Superscript 156.95 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] 16 1 Superscript 157.16 Å² [M+K]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] 15 1 Superscript 145.94 Å² [M+H-H2O]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] 19 1 Superscript 4 https://www.sciencedirect.com/science/article/pii/S0021967318301894 150.3 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)] 14 1 Superscript 5 https://pubs.rsc.org/en/content/articlelanding/2018/ay/c7ay02808c 150 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated] 12 1 Superscript 6 https://pubs.acs.org/doi/abs/10.1021/acs.analchem.7b01709 149 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] 12 1 Superscript 163 S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476 158.54 Å² [M+Na]+ 16 1 Superscript 149.11 Å² [M+H]+ 15 1 Superscript

Kovats Retention Index The Kovats retention index is a dimensionless quantity that characterizes the rate at which a compound is processed through a gas chromatography column. https://goldbook.iupac.org/terms/view/R05360 ThisSection 2 Name Value CommaSeparated 161 Standard non-polar 2296 2259 2259 2290 2285 2310 2337 2340 2280.2 2316.8 2275 2270 2290 2310 2290 161 Semi-standard non-polar 2397.4 2332.5 2306.3 2347.5 2335.1 2312 2314

Other Experimental Properties Other experimental properties of this chemical. 59 PEER REVIEWED Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 148 STABLE TO HYDROLYSIS

SpringerMaterials Properties List of properties available in SpringerMaterials, which has chemical and physical property data pertinent to materials science, physics, chemistry and engineering. https://pubchem.ncbi.nlm.nih.gov/docs/springermaterials Columns 179 15N nuclear magnetic resonance spectrum 0 39 https://materials.springer.com/search?searchTerm=Dibenzo%5Bb%2Cf%5Dazepine-5-carboxylic+acid+amide&propertyFacet=15N%20nuclear%20magnetic%20resonance%20spectrum&substanceId=smsid_bneuthoaaluflmue Chemical shift 0 14 https://materials.springer.com/search?searchTerm=Dibenzo%5Bb%2Cf%5Dazepine-5-carboxylic+acid+amide&propertyFacet=chemical%20shift&substanceId=smsid_bneuthoaaluflmue Spin-spin coupling constant 0 27 https://materials.springer.com/search?searchTerm=Dibenzo%5Bb%2Cf%5Dazepine-5-carboxylic+acid+amide&propertyFacet=spin-spin%20coupling%20constant&substanceId=smsid_bneuthoaaluflmue

Chemical Classes Chemical classes are groupings that relate chemicals by similar features. Chemicals can be classified by their structure (e.g., hydrocarbons), uses (e.g., pesticides), physical properties, radiological properties, or other factors.

Human Drugs Chemicals are used as active ingredients in human drug products. 35 Human drug -> Prescription 36 Human drug -> Prescription 37 Human drug -> Prescription 38 Human drug -> Prescription; None (Tentative Approval); Discontinued; Active ingredient (CARBAMAZEPINE) 88 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554 39 Human drug -> Prescription; Discontinued 40 Human drug -> Discontinued 41 Human drug -> Prescription; Discontinued 42 Human drug -> Prescription 163 S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664 Pharmaceuticals

Spectral Information Spectral data for this compound, including 1-D and 2-D nuclear magnetic resonance (NMR), Infrared (IR), Raman, and Ultraviolet (UV) spectroscopy, mass spectrometry (MS), and chromatography.

1D NMR Spectra One-dimensional (1D) nuclear magnetic resonance (NMR) spectra. ThisSection 2 Name Value 2

1H NMR Spectra Hydrogen-1 nuclear magnetic resonance (NMR) spectroscopy (also known as H1 NMR or proton NMR) is a version of NMR spectroscopy used to elucidate the structure of hydrogen-containing compounds. ThisSection 2 Name Value 2 61 Spectra ID https://hmdb.ca/spectra/nmr_one_d/2324 2324 61 Instrument Type JEOL 61 Frequency 400 MHz 61 Solvent CDCl3 61 Shifts [ppm]:Intensity 7.36:153.00, 7.35:198.00, 7.33:361.00, 7.30:264.00, 7.29:284.00, 6.91:1000.00, 7.40:387.00, 7.40:328.00, 4.96:47.00, 7.34:428.00, 7.38:167.00, 7.28:112.00, 7.46:202.00, 7.46:186.00, 7.32:340.00, 7.41:31.00, 7.44:432.00, 7.41:288.00, 7.42:271.00, 7.29:181.00, 7.39:163.00, 7.31:329.00, 7.38:216.00, 7.44:435.00, 7.28:114.00 61 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/nmr.cgi?peaks=7.36:153.00,7.35:198.00,7.33:361.00,7.30:264.00,7.29:284.00,6.91:1000.00,7.40:387.00,7.40:328.00,4.96:47.00,7.34:428.00,7.38:167.00,7.28:112.00,7.46:202.00,7.46:186.00,7.32:340.00,7.41:31.00,7.44:432.00,7.41:288.00,7.42:271.00,7.29:181.00,7.39:163.00,7.31:329.00,7.38:216.00,7.44:435.00,7.28:114.00 https://pubchem.ncbi.nlm.nih.gov/image/nmr.cgi?peaks=7.36:153.00,7.35:198.00,7.33:361.00,7.30:264.00,7.29:284.00,6.91:1000.00,7.40:387.00,7.40:328.00,4.96:47.00,7.34:428.00,7.38:167.00,7.28:112.00,7.46:202.00,7.46:186.00,7.32:340.00,7.41:31.00,7.44:432.00,7.41:288.00,7.42:271.00,7.29:181.00,7.39:163.00,7.31:329.00,7.38:216.00,7.44:435.00,7.28:114.00 image/svg 177 Source of Spectrum Sigma-Aldrich Co. LLC. 177 Source of Sample Sigma-Aldrich Co. LLC. 177 Catalog Number 309486 177 Copyright Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved. 177 Thumbnail https://spectrabase.com/spectrum/12aC1lu8DXK https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/13594817_1 image/png

13C NMR Spectra Carbon-13 nuclear magnetic resonance (NMR) spectroscopy (also known as 13C NMR) is a version of NMR spectroscopy used to elucidate the structure of carbon-containing compounds. ThisSection 2 Name Value 2 173 Copyright Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved. 173 Thumbnail https://spectrabase.com/spectrum/9dvbiAkhs0c https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4772156_1 image/png 176 Source of Spectrum Sigma-Aldrich Co. LLC. 176 Source of Sample Sigma-Aldrich Co. LLC. 176 Catalog Number 309486 176 Copyright Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved. 176 Thumbnail https://spectrabase.com/spectrum/C4UFfo9EkbB https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/13594816_1 image/png

Mass Spectrometry Mass spectrometry (MS or mass spec) is a technique to determine molecular structure through ionization and fragmentation of the parent compound into smaller components. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Spectroscopy/Mass_Spectrometry ThisSection 2 Name Value 2

GC-MS Data from gas chromatography-mass spectrometry (GC-MS) experiments. https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Structure_and_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_(Schaller)/II%3A_Practical_Aspects_of_Structure_-_Purification_and_Spectroscopy/06%3A_Introductory_Mass_Spectrometry/6.03%3A_GC-MS_and_LC-MS ThisSection 2 Name Value 2 149 NIST Number 236284 149 Library Main library 149 Total Peaks 90 149 m/z Top Peak 193 149 m/z 2nd Highest 192 149 m/z 3rd Highest 236 149 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/185235_1 image/png 150 NIST Number 286365 150 Library Replicate library 150 Total Peaks 109 150 m/z Top Peak 193 150 m/z 2nd Highest 192 150 m/z 3rd Highest 165 150 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275714_1 image/png 151 NIST Number 113838 151 Library Replicate library 151 Total Peaks 67 151 m/z Top Peak 193 151 m/z 2nd Highest 192 151 m/z 3rd Highest 191 151 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275718_1 image/png 152 NIST Number 417061 152 Library Replicate library 152 Total Peaks 124 152 m/z Top Peak 193 152 m/z 2nd Highest 192 152 m/z 3rd Highest 191 152 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275719_1 image/png 153 NIST Number 247761 153 Library Replicate library 153 Total Peaks 86 153 m/z Top Peak 193 153 m/z 2nd Highest 192 153 m/z 3rd Highest 236 153 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275723_1 image/png 154 NIST Number 250712 154 Library Replicate library 154 Total Peaks 110 154 m/z Top Peak 193 154 m/z 2nd Highest 192 154 m/z 3rd Highest 236 154 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275724_1 image/png 155 NIST Number 312908 155 Library Replicate library 155 Total Peaks 84 155 m/z Top Peak 193 155 m/z 2nd Highest 192 155 m/z 3rd Highest 236 155 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275725_1 image/png 156 NIST Number 379526 156 Library Replicate library 156 Total Peaks 85 156 m/z Top Peak 193 156 m/z 2nd Highest 192 156 m/z 3rd Highest 236 156 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/275726_1 image/png 168 Source of Spectrum Mass Spectrometry Committee of the Toxicology Section of the American Academy of Forensic Sciences 168 Copyright Copyright © 2012-2024 John Wiley & Sons, Inc. Portions provided by AAFS, Toxicology Section. All Rights Reserved. 168 Thumbnail https://spectrabase.com/spectrum/Hm9SRztRxaB https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4772149_1 image/png 169 Source of Spectrum Mass Spectrometry Committee of the Toxicology Section of the American Academy of Forensic Sciences 169 Copyright Copyright © 2012-2024 John Wiley & Sons, Inc. Portions provided by AAFS, Toxicology Section. All Rights Reserved. 169 Thumbnail https://spectrabase.com/spectrum/KpxcONsO0mx https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4772150_1 image/png

MS-MS Data from tandem mass spectrometry (MS-MS) experiments. https://goldbook.iupac.org/terms/view/T06250 ThisSection 2 Name Value 2 62 Spectra ID https://hmdb.ca/spectra/ms_ms/2226189 2226189 62 Ionization Mode Positive 62 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query==exists(splash.splash:%27splash10-000i-0090000000-01c635992f1dc0325f99%27) splash10-000i-0090000000-01c635992f1dc0325f99 62 Top 5 Peaks 237.102 100 238.1052 14.48 194.0964 8.57 62 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.102:100,238.1052:14.48,194.0964:8.57 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.102:100,238.1052:14.48,194.0964:8.57 image/svg 63 Spectra ID https://hmdb.ca/spectra/ms_ms/2228533 2228533 63 Ionization Mode Positive 63 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query==exists(splash.splash:%27splash10-0006-0910000000-9ca4cd5a8ec9aea2fed3%27) splash10-0006-0910000000-9ca4cd5a8ec9aea2fed3 63 Top 5 Peaks 194.0963 100 237.1021 19.98 192.0806 15.60 195.0941 11.56 193.0883 3.39 63 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:100,237.1021:19.98,192.0806:15.60,195.0941:11.56,193.0883:3.39 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:100,237.1021:19.98,192.0806:15.60,195.0941:11.56,193.0883:3.39 image/svg 64 Spectra ID https://hmdb.ca/spectra/ms_ms/2228583 2228583 64 Ionization Mode Positive 64 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query==exists(splash.splash:%27splash10-0006-0900000000-19fd4587bbfb341238aa%27) splash10-0006-0900000000-19fd4587bbfb341238aa 64 Top 5 Peaks 194.0958 100 193.0882 97.96 192.0804 49.09 179.0726 38.70 165.0694 20.24 64 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:100,193.0882:97.96,192.0804:49.09,179.0726:38.70,165.0694:20.24 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:100,193.0882:97.96,192.0804:49.09,179.0726:38.70,165.0694:20.24 image/svg 65 Spectra ID https://hmdb.ca/spectra/ms_ms/2230845 2230845 65 Ionization Mode Positive 65 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query==exists(splash.splash:%27splash10-0006-0900000000-4c95ec21e004e0175176%27) splash10-0006-0900000000-4c95ec21e004e0175176 65 Top 5 Peaks 194.0958 100 193.0873 15.77 195.0994 13.83 165.0695 1.41 65 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:100,193.0873:15.77,195.0994:13.83,165.0695:1.41 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:100,193.0873:15.77,195.0994:13.83,165.0695:1.41 image/svg 66 Spectra ID https://hmdb.ca/spectra/ms_ms/2231046 2231046 66 Ionization Mode Positive 66 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query==exists(splash.splash:%27splash10-000l-0690000000-664bce4bf598cb05bbf1%27) splash10-000l-0690000000-664bce4bf598cb05bbf1 66 Top 5 Peaks 237.1008 100 194.0952 60.29 192.0788 10.40 220.074 1.97 66 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1008:100,194.0952:60.29,192.0788:10.40,220.074:1.97 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1008:100,194.0952:60.29,192.0788:10.40,220.074:1.97 image/svg 67 Spectra ID https://hmdb.ca/spectra/ms_ms/2231288 2231288 67 Ionization Mode Positive 67 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query==exists(splash.splash:%27splash10-0006-0900000000-1bd5544bba91616cb27c%27) splash10-0006-0900000000-1bd5544bba91616cb27c 67 Top 5 Peaks 194.0964 100 193.0888 59.89 192.081 41.20 179.073 29.57 165.07 15.23 67 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:100,193.0888:59.89,192.081:41.20,179.073:29.57,165.07:15.23 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:100,193.0888:59.89,192.081:41.20,179.073:29.57,165.07:15.23 image/svg 157 NIST Number 1000311 157 Instrument Type IT/ion trap 157 Collision Energy 0 157 Spectrum Type MS2 157 Precursor Type [M+H]+ 157 Precursor m/z 237.1022 157 Total Peaks 5 157 m/z Top Peak 194 157 m/z 2nd Highest 220 157 m/z 3rd Highest 237 157 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/284843_1 image/png 158 NIST Number 1000376 158 Instrument Type IT/ion trap 158 Collision Energy 0 158 Spectrum Type MS2 158 Precursor Type [M+H]+ 158 Precursor m/z 237.1022 158 Total Peaks 8 158 m/z Top Peak 194 158 m/z 2nd Highest 220 158 m/z 3rd Highest 237 158 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/284902_1 image/png 159 NIST Number 1000746 159 Instrument Type IT/ion trap 159 Collision Energy 0 159 Spectrum Type MS2 159 Precursor Type [M+H]+ 159 Precursor m/z 237.1022 159 Total Peaks 5 159 m/z Top Peak 237 159 m/z 2nd Highest 194 159 m/z 3rd Highest 195 159 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/285028_1 image/png 160 NIST Number 1053460 160 Instrument Type IT/ion trap 160 Collision Energy 0 160 Spectrum Type MS2 160 Precursor Type [M+H]+ 160 Precursor m/z 237.1022 160 Total Peaks 6 160 m/z Top Peak 194.1 160 m/z 2nd Highest 220 160 m/z 3rd Highest 192.1 160 Thumbnail https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/287578_1 image/png

LC-MS Data from liquid chromatography-mass spectrometry (LC-MS) experiments. https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Structure_and_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_(Schaller)/II%3A_Practical_Aspects_of_Structure_-_Purification_and_Spectroscopy/06%3A_Introductory_Mass_Spectrometry/6.03%3A_GC-MS_and_LC-MS ThisSection 2 Name Value 2 75 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-ACES_SU-AS000160 MSBNK-ACES_SU-AS000160 75 Authors ACESx, Jonathan W. Martin Group 75 Instrument QExactive Orbitrap HF-X (Thermo Scientific) 75 Instrument Type LC-ESI-QFT 75 MS Level MS2 75 Ionization Mode POSITIVE 75 Ionization ESI 75 Collision Energy Ramp 20%-70% (nominal) 75 Fragmentation Mode HCD 75 Column Name Waters; Acquity UPLC BEH C18, 2.1 x 100 mm, 1.7 um, Waters 75 Retention Time 13.9213 75 Top 5 Peaks 237.10194 999 194.09634 994 192.08101 268 193.08852 234 179.07309 104 75 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000f-0950000000-c8b6bbff2c2a1597cc91 splash10-000f-0950000000-c8b6bbff2c2a1597cc91 75 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.10194:999,194.09634:994,192.08101:268,193.08852:234,179.07309:104 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.10194:999,194.09634:994,192.08101:268,193.08852:234,179.07309:104 image/svg 75 License CC BY 76 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Athens_Univ-AU112001 MSBNK-Athens_Univ-AU112001 76 Authors Nikiforos Alygizakis, Anna Bletsou, Nikolaos Thomaidis, University of Athens 76 Instrument Bruker maXis Impact 76 Instrument Type LC-ESI-QTOF 76 MS Level MS2 76 Ionization Mode POSITIVE 76 Ionization ESI 76 Collision Energy 10 eV 76 Fragmentation Mode CID 76 Column Name Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo 76 Retention Time 7.3 min 76 Precursor m/z 237.1022 76 Precursor Adduct [M+H]+ 76 Top 5 Peaks 237.102 999 238.1052 144 194.0964 85 195.0996 9 239.1081 6 76 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0090000000-be63f70e101a786a369b splash10-000i-0090000000-be63f70e101a786a369b 76 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.102:999,238.1052:144,194.0964:85,195.0996:9,239.1081:6 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.102:999,238.1052:144,194.0964:85,195.0996:9,239.1081:6 image/svg 76 License CC BY-SA 77 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Athens_Univ-AU112002 MSBNK-Athens_Univ-AU112002 77 Authors Nikiforos Alygizakis, Anna Bletsou, Nikolaos Thomaidis, University of Athens 77 Instrument Bruker maXis Impact 77 Instrument Type LC-ESI-QTOF 77 MS Level MS2 77 Ionization Mode POSITIVE 77 Ionization ESI 77 Collision Energy 20 eV 77 Fragmentation Mode CID 77 Column Name Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo 77 Retention Time 7.3 min 77 Precursor m/z 237.1022 77 Precursor Adduct [M+H]+ 77 Top 5 Peaks 194.0963 999 237.1021 199 192.0806 155 195.0941 115 193.0883 33 77 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0910000000-f171a56d3bbeaef24ff4 splash10-0006-0910000000-f171a56d3bbeaef24ff4 77 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,237.1021:199,192.0806:155,195.0941:115,193.0883:33 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,237.1021:199,192.0806:155,195.0941:115,193.0883:33 image/svg 77 License CC BY-SA 78 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Athens_Univ-AU112003 MSBNK-Athens_Univ-AU112003 78 Authors Nikiforos Alygizakis, Anna Bletsou, Nikolaos Thomaidis, University of Athens 78 Instrument Bruker maXis Impact 78 Instrument Type LC-ESI-QTOF 78 MS Level MS2 78 Ionization Mode POSITIVE 78 Ionization ESI 78 Collision Energy 30 eV 78 Fragmentation Mode CID 78 Column Name Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo 78 Retention Time 7.3 min 78 Precursor m/z 237.1022 78 Precursor Adduct [M+H]+ 78 Top 5 Peaks 194.0958 999 193.0873 157 195.0994 138 165.0695 14 191.0727 9 78 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-a82def037961e9b94a9a splash10-0006-0900000000-a82def037961e9b94a9a 78 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:999,193.0873:157,195.0994:138,165.0695:14,191.0727:9 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:999,193.0873:157,195.0994:138,165.0695:14,191.0727:9 image/svg 78 License CC BY-SA 79 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Athens_Univ-AU112004 MSBNK-Athens_Univ-AU112004 79 Authors Nikiforos Alygizakis, Anna Bletsou, Nikolaos Thomaidis, University of Athens 79 Instrument Bruker maXis Impact 79 Instrument Type LC-ESI-QTOF 79 MS Level MS2 79 Ionization Mode POSITIVE 79 Ionization ESI 79 Collision Energy 40 eV 79 Fragmentation Mode CID 79 Column Name Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo 79 Retention Time 7.3 min 79 Precursor m/z 237.1022 79 Precursor Adduct [M+H]+ 79 Top 5 Peaks 194.0958 999 193.0882 978 192.0804 490 179.0726 386 165.0694 202 79 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-484ce005b4ae5d01fc2a splash10-0006-0900000000-484ce005b4ae5d01fc2a 79 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:999,193.0882:978,192.0804:490,179.0726:386,165.0694:202 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:999,193.0882:978,192.0804:490,179.0726:386,165.0694:202 image/svg 79 License CC BY-SA 80 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Athens_Univ-AU112005 MSBNK-Athens_Univ-AU112005 80 Authors Nikiforos Alygizakis, Anna Bletsou, Nikolaos Thomaidis, University of Athens 80 Instrument Bruker maXis Impact 80 Instrument Type LC-ESI-QTOF 80 MS Level MS2 80 Ionization Mode POSITIVE 80 Ionization ESI 80 Collision Energy 50 eV 80 Fragmentation Mode CID 80 Column Name Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo 80 Retention Time 7.3 min 80 Precursor m/z 237.1022 80 Precursor Adduct [M+H]+ 80 Top 5 Peaks 193.088 999 192.0803 627 165.0693 437 179.0724 431 191.0728 343 80 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-a6992953eac16c120e74 splash10-0006-0900000000-a6992953eac16c120e74 80 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.088:999,192.0803:627,165.0693:437,179.0724:431,191.0728:343 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.088:999,192.0803:627,165.0693:437,179.0724:431,191.0728:343 image/svg 80 License CC BY-SA 81 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Athens_Univ-AU112006 MSBNK-Athens_Univ-AU112006 81 Authors Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens 81 Instrument Bruker maXis Impact 81 Instrument Type LC-ESI-QTOF 81 MS Level MS2 81 Ionization Mode POSITIVE 81 Ionization ESI 81 Collision Energy Ramp 19.3-29.0 eV 81 Fragmentation Mode CID 81 Column Name Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo 81 Retention Time 7.504 min 81 Precursor m/z 237.1022 81 Precursor Adduct [M+H]+ 81 Top 5 Peaks 194.0963 999 192.0802 297 237.102 267 195.0991 200 193.0867 124 81 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0910000000-3c1c311102f09cdbc413 splash10-0006-0910000000-3c1c311102f09cdbc413 81 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0802:297,237.102:267,195.0991:200,193.0867:124 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0802:297,237.102:267,195.0991:200,193.0867:124 image/svg 81 License CC BY 82 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107610 MSBNK-BAFG-CSL2311107610 82 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 82 Instrument TripleTOF 5600 SCIEX 82 Instrument Type LC-ESI-QTOF 82 MS Level MS2 82 Ionization Mode POSITIVE 82 Ionization ESI 82 Collision Energy 150 82 Fragmentation Mode CID 82 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 82 Retention Time 8.87 min 82 Precursor m/z 237.1022 82 Precursor Adduct [M+H]+ 82 Top 5 Peaks 74.0183 999 86.0167 659 98.016 615 85.0108 320 110.0147 320 82 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0079-9400000000-1cfe6a77ed24d54d2490 splash10-0079-9400000000-1cfe6a77ed24d54d2490 82 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=74.0183:999,86.0167:659,98.016:615,85.0108:320,110.0147:320 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=74.0183:999,86.0167:659,98.016:615,85.0108:320,110.0147:320 image/svg 82 License dl-de/by-2-0 83 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107611 MSBNK-BAFG-CSL2311107611 83 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 83 Instrument TripleTOF 5600 SCIEX 83 Instrument Type LC-ESI-QTOF 83 MS Level MS2 83 Ionization Mode POSITIVE 83 Ionization ESI 83 Collision Energy 40 83 Fragmentation Mode CID 83 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 83 Retention Time 8.87 min 83 Precursor m/z 237.1022 83 Precursor Adduct [M+H]+ 83 Top 5 Peaks 194.0963 999 192.0806 704 193.0885 601 179.0727 319 165.0697 234 83 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-b0610ffbd5df0b1b7a95 splash10-0006-0900000000-b0610ffbd5df0b1b7a95 83 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:704,193.0885:601,179.0727:319,165.0697:234 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:704,193.0885:601,179.0727:319,165.0697:234 image/svg 83 License dl-de/by-2-0 84 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107612 MSBNK-BAFG-CSL2311107612 84 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 84 Instrument TripleTOF 5600 SCIEX 84 Instrument Type LC-ESI-QTOF 84 MS Level MS2 84 Ionization Mode POSITIVE 84 Ionization ESI 84 Collision Energy 100 84 Fragmentation Mode CID 84 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 84 Retention Time 8.87 min 84 Precursor m/z 237.1022 84 Precursor Adduct [M+H]+ 84 Top 5 Peaks 163.0541 999 190.0646 645 164.058 528 139.0537 515 89.04 485 84 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-03du-1900000000-1a937eac6270c0ca5724 splash10-03du-1900000000-1a937eac6270c0ca5724 84 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0541:999,190.0646:645,164.058:528,139.0537:515,89.04:485 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0541:999,190.0646:645,164.058:528,139.0537:515,89.04:485 image/svg 84 License dl-de/by-2-0 85 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107613 MSBNK-BAFG-CSL2311107613 85 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 85 Instrument TripleTOF 5600 SCIEX 85 Instrument Type LC-ESI-QTOF 85 MS Level MS2 85 Ionization Mode POSITIVE 85 Ionization ESI 85 Collision Energy 20 85 Fragmentation Mode CID 85 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 85 Retention Time 8.87 min 85 Precursor m/z 237.1022 85 Precursor Adduct [M+H]+ 85 Top 5 Peaks 237.1022 999 194.0962 890 192.0808 176 193.0881 24 85 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000f-0980000000-a0218572124efa0d6302 splash10-000f-0980000000-a0218572124efa0d6302 85 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0962:890,192.0808:176,193.0881:24, https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0962:890,192.0808:176,193.0881:24, image/svg 85 License dl-de/by-2-0 86 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107614 MSBNK-BAFG-CSL2311107614 86 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 86 Instrument TripleTOF 5600 SCIEX 86 Instrument Type LC-ESI-QTOF 86 MS Level MS2 86 Ionization Mode POSITIVE 86 Ionization ESI 86 Collision Energy 80 86 Fragmentation Mode CID 86 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 86 Retention Time 8.87 min 86 Precursor m/z 237.1022 86 Precursor Adduct [M+H]+ 86 Top 5 Peaks 191.0736 999 190.0655 683 165.0698 681 163.0548 526 164.0611 489 86 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-01ox-0900000000-7ba47794454d2a89e9fe splash10-01ox-0900000000-7ba47794454d2a89e9fe 86 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=191.0736:999,190.0655:683,165.0698:681,163.0548:526,164.0611:489 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=191.0736:999,190.0655:683,165.0698:681,163.0548:526,164.0611:489 image/svg 86 License dl-de/by-2-0 87 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107615 MSBNK-BAFG-CSL2311107615 87 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 87 Instrument TripleTOF 5600 SCIEX 87 Instrument Type LC-ESI-QTOF 87 MS Level MS2 87 Ionization Mode POSITIVE 87 Ionization ESI 87 Collision Energy 70 87 Fragmentation Mode CID 87 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 87 Retention Time 8.87 min 87 Precursor m/z 237.1022 87 Precursor Adduct [M+H]+ 87 Top 5 Peaks 191.0727 999 165.0693 821 192.0808 601 190.0648 469 178.0653 400 87 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-00kf-0900000000-6bd970c25300ec70efa8 splash10-00kf-0900000000-6bd970c25300ec70efa8 87 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=191.0727:999,165.0693:821,192.0808:601,190.0648:469,178.0653:400 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=191.0727:999,165.0693:821,192.0808:601,190.0648:469,178.0653:400 image/svg 87 License dl-de/by-2-0 88 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107616 MSBNK-BAFG-CSL2311107616 88 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 88 Instrument TripleTOF 5600 SCIEX 88 Instrument Type LC-ESI-QTOF 88 MS Level MS2 88 Ionization Mode POSITIVE 88 Ionization ESI 88 Collision Energy 60 88 Fragmentation Mode CID 88 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 88 Retention Time 8.87 min 88 Precursor m/z 237.1022 88 Precursor Adduct [M+H]+ 88 Top 5 Peaks 192.0812 999 191.0733 911 165.0702 724 193.0889 720 179.0729 472 88 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-54e4b54707f347a7c8e2 splash10-0006-0900000000-54e4b54707f347a7c8e2 88 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=192.0812:999,191.0733:911,165.0702:724,193.0889:720,179.0729:472 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=192.0812:999,191.0733:911,165.0702:724,193.0889:720,179.0729:472 image/svg 88 License dl-de/by-2-0 89 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107617 MSBNK-BAFG-CSL2311107617 89 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 89 Instrument TripleTOF 5600 SCIEX 89 Instrument Type LC-ESI-QTOF 89 MS Level MS2 89 Ionization Mode POSITIVE 89 Ionization ESI 89 Collision Energy 30 89 Fragmentation Mode CID 89 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 89 Retention Time 8.87 min 89 Precursor m/z 237.1022 89 Precursor Adduct [M+H]+ 89 Top 5 Peaks 194.0958 999 192.081 266 193.0884 92 237.1031 33 179.0728 31 89 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-bd9fcd1baca65453380c splash10-0006-0900000000-bd9fcd1baca65453380c 89 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:999,192.081:266,193.0884:92,237.1031:33,179.0728:31 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0958:999,192.081:266,193.0884:92,237.1031:33,179.0728:31 image/svg 89 License dl-de/by-2-0 90 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107618 MSBNK-BAFG-CSL2311107618 90 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 90 Instrument TripleTOF 5600 SCIEX 90 Instrument Type LC-ESI-QTOF 90 MS Level MS2 90 Ionization Mode POSITIVE 90 Ionization ESI 90 Collision Energy 140 90 Fragmentation Mode CID 90 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 90 Retention Time 8.87 min 90 Precursor m/z 237.1022 90 Precursor Adduct [M+H]+ 90 Top 5 Peaks 74.0192 999 98.0159 682 86.017 668 89.0409 537 87.0246 475 90 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-9500000000-8cc698563fc3420ecd6e splash10-000i-9500000000-8cc698563fc3420ecd6e 90 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=74.0192:999,98.0159:682,86.017:668,89.0409:537,87.0246:475 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=74.0192:999,98.0159:682,86.017:668,89.0409:537,87.0246:475 image/svg 90 License dl-de/by-2-0 91 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107619 MSBNK-BAFG-CSL2311107619 91 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 91 Instrument TripleTOF 5600 SCIEX 91 Instrument Type LC-ESI-QTOF 91 MS Level MS2 91 Ionization Mode POSITIVE 91 Ionization ESI 91 Collision Energy 90 91 Fragmentation Mode CID 91 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 91 Retention Time 8.87 min 91 Precursor m/z 237.1022 91 Precursor Adduct [M+H]+ 91 Top 5 Peaks 163.0546 999 190.0653 951 191.0726 827 139.0543 646 164.0603 646 91 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-01p6-1900000000-8e72bed11d65c186a646 splash10-01p6-1900000000-8e72bed11d65c186a646 91 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0546:999,190.0653:951,191.0726:827,139.0543:646,164.0603:646 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0546:999,190.0653:951,191.0726:827,139.0543:646,164.0603:646 image/svg 91 License dl-de/by-2-0 92 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107620 MSBNK-BAFG-CSL2311107620 92 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 92 Instrument TripleTOF 5600 SCIEX 92 Instrument Type LC-ESI-QTOF 92 MS Level MS2 92 Ionization Mode POSITIVE 92 Ionization ESI 92 Collision Energy 50 92 Fragmentation Mode CID 92 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 92 Retention Time 8.87 min 92 Precursor m/z 237.1022 92 Precursor Adduct [M+H]+ 92 Top 5 Peaks 193.0881 999 192.0804 661 179.0725 530 194.0964 451 165.0695 428 92 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-422eaa210630abcc7148 splash10-0006-0900000000-422eaa210630abcc7148 92 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0881:999,192.0804:661,179.0725:530,194.0964:451,165.0695:428 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0881:999,192.0804:661,179.0725:530,194.0964:451,165.0695:428 image/svg 92 License dl-de/by-2-0 93 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107621 MSBNK-BAFG-CSL2311107621 93 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 93 Instrument TripleTOF 5600 SCIEX 93 Instrument Type LC-ESI-QTOF 93 MS Level MS2 93 Ionization Mode POSITIVE 93 Ionization ESI 93 Collision Energy 120 93 Fragmentation Mode CID 93 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 93 Retention Time 8.87 min 93 Precursor m/z 237.1022 93 Precursor Adduct [M+H]+ 93 Top 5 Peaks 163.0539 999 89.04 655 74.0184 483 113.038 387 162.0451 383 93 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-03dr-4900000000-025df769dc8bd2b824f4 splash10-03dr-4900000000-025df769dc8bd2b824f4 93 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0539:999,89.04:655,74.0184:483,113.038:387,162.0451:383 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0539:999,89.04:655,74.0184:483,113.038:387,162.0451:383 image/svg 93 License dl-de/by-2-0 94 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107622 MSBNK-BAFG-CSL2311107622 94 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 94 Instrument TripleTOF 5600 SCIEX 94 Instrument Type LC-ESI-QTOF 94 MS Level MS2 94 Ionization Mode POSITIVE 94 Ionization ESI 94 Collision Energy 110 94 Fragmentation Mode CID 94 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 94 Retention Time 8.87 min 94 Precursor m/z 237.1022 94 Precursor Adduct [M+H]+ 94 Top 5 Peaks 163.0541 999 89.04 558 139.0545 432 150.0465 397 190.0655 392 94 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-03dr-3900000000-e17d0b25d78625c3c495 splash10-03dr-3900000000-e17d0b25d78625c3c495 94 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0541:999,89.04:558,139.0545:432,150.0465:397,190.0655:392 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=163.0541:999,89.04:558,139.0545:432,150.0465:397,190.0655:392 image/svg 94 License dl-de/by-2-0 95 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107623 MSBNK-BAFG-CSL2311107623 95 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 95 Instrument TripleTOF 5600 SCIEX 95 Instrument Type LC-ESI-QTOF 95 MS Level MS2 95 Ionization Mode POSITIVE 95 Ionization ESI 95 Collision Energy 40 95 Fragmentation Mode CID 95 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 95 Retention Time 8.87 min 95 Precursor m/z 237.1022 95 Precursor Adduct [M+H]+ 95 Top 5 Peaks 194.0959 999 193.0885 528 192.081 429 179.0732 240 165.0699 129 95 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-30b6e1fce78a0c843da0 splash10-0006-0900000000-30b6e1fce78a0c843da0 95 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0959:999,193.0885:528,192.081:429,179.0732:240,165.0699:129 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0959:999,193.0885:528,192.081:429,179.0732:240,165.0699:129 image/svg 95 License dl-de/by-2-0 96 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107624 MSBNK-BAFG-CSL2311107624 96 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 96 Instrument TripleTOF 5600 SCIEX 96 Instrument Type LC-ESI-QTOF 96 MS Level MS2 96 Ionization Mode POSITIVE 96 Ionization ESI 96 Collision Energy 10 96 Fragmentation Mode CID 96 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 96 Retention Time 8.87 min 96 Precursor m/z 237.1022 96 Precursor Adduct [M+H]+ 96 Top 5 Peaks 237.1023 999 194.0968 72 96 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0090000000-6e669d93add47bc33437 splash10-000i-0090000000-6e669d93add47bc33437 96 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1023:999,194.0968:72, https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1023:999,194.0968:72, image/svg 96 License dl-de/by-2-0 97 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-BAFG-CSL2311107625 MSBNK-BAFG-CSL2311107625 97 Authors Kevin S. Jewell; Björn Ehlig; Arne Wick 97 Instrument TripleTOF 5600 SCIEX 97 Instrument Type LC-ESI-QTOF 97 MS Level MS2 97 Ionization Mode POSITIVE 97 Ionization ESI 97 Collision Energy 130 97 Fragmentation Mode CID 97 Column Name Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent 97 Retention Time 8.87 min 97 Precursor m/z 237.1022 97 Precursor Adduct [M+H]+ 97 Top 5 Peaks 74.0188 999 163.0546 896 89.0406 793 98.0158 712 87.0253 675 97 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-03dr-8900000000-59ff4c620260a007463f splash10-03dr-8900000000-59ff4c620260a007463f 97 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=74.0188:999,163.0546:896,89.0406:793,98.0158:712,87.0253:675 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=74.0188:999,163.0546:896,89.0406:793,98.0158:712,87.0253:675 image/svg 97 License dl-de/by-2-0 98 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019401 MSBNK-Eawag-EA019401 98 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 98 Instrument LTQ Orbitrap XL Thermo Scientific 98 Instrument Type LC-ESI-ITFT 98 MS Level MS2 98 Ionization Mode POSITIVE 98 Ionization ESI 98 Collision Energy 35 % (nominal) 98 Fragmentation Mode CID 98 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 98 Retention Time 7.8 min 98 Precursor m/z 237.1022 98 Precursor Adduct [M+H]+ 98 Top 5 Peaks 194.0963 999 220.0754 87 192.0807 53 98 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-7a1010be5231131649eb splash10-0006-0900000000-7a1010be5231131649eb 98 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,220.0754:87,192.0807:53, https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,220.0754:87,192.0807:53, image/svg 98 License CC BY 99 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019402 MSBNK-Eawag-EA019402 99 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 99 Instrument LTQ Orbitrap XL Thermo Scientific 99 Instrument Type LC-ESI-ITFT 99 MS Level MS2 99 Ionization Mode POSITIVE 99 Ionization ESI 99 Collision Energy 15 % (nominal) 99 Fragmentation Mode HCD 99 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 99 Retention Time 7.8 min 99 Precursor m/z 237.1022 99 Precursor Adduct [M+H]+ 99 Top 5 Peaks 237.1022 999 194.0961 20 192.0808 2 193.0876 1 179.0732 1 99 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0090000000-51ef94c86cca9b541780 splash10-000i-0090000000-51ef94c86cca9b541780 99 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0961:20,192.0808:2,193.0876:1,179.0732:1 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0961:20,192.0808:2,193.0876:1,179.0732:1 image/svg 99 License CC BY 100 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019403 MSBNK-Eawag-EA019403 100 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 100 Instrument LTQ Orbitrap XL Thermo Scientific 100 Instrument Type LC-ESI-ITFT 100 MS Level MS2 100 Ionization Mode POSITIVE 100 Ionization ESI 100 Collision Energy 30 % (nominal) 100 Fragmentation Mode HCD 100 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 100 Retention Time 7.8 min 100 Precursor m/z 237.1022 100 Precursor Adduct [M+H]+ 100 Top 5 Peaks 237.1022 999 194.0964 490 192.0807 67 220.0751 16 191.0733 2 100 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0490000000-4484ac1671912bc60ba9 splash10-000i-0490000000-4484ac1671912bc60ba9 100 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0964:490,192.0807:67,220.0751:16,191.0733:2 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0964:490,192.0807:67,220.0751:16,191.0733:2 image/svg 100 License CC BY 101 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019404 MSBNK-Eawag-EA019404 101 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 101 Instrument LTQ Orbitrap XL Thermo Scientific 101 Instrument Type LC-ESI-ITFT 101 MS Level MS2 101 Ionization Mode POSITIVE 101 Ionization ESI 101 Collision Energy 45 % (nominal) 101 Fragmentation Mode HCD 101 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 101 Retention Time 7.8 min 101 Precursor m/z 237.1022 101 Precursor Adduct [M+H]+ 101 Top 5 Peaks 194.0964 999 192.0807 214 237.1021 180 193.0885 15 220.0752 6 101 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0910000000-e5ca06888593ada95f15 splash10-0006-0910000000-e5ca06888593ada95f15 101 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,192.0807:214,237.1021:180,193.0885:15,220.0752:6 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,192.0807:214,237.1021:180,193.0885:15,220.0752:6 image/svg 101 License CC BY 102 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019405 MSBNK-Eawag-EA019405 102 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 102 Instrument LTQ Orbitrap XL Thermo Scientific 102 Instrument Type LC-ESI-ITFT 102 MS Level MS2 102 Ionization Mode POSITIVE 102 Ionization ESI 102 Collision Energy 60 % (nominal) 102 Fragmentation Mode HCD 102 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 102 Retention Time 7.8 min 102 Precursor m/z 237.1022 102 Precursor Adduct [M+H]+ 102 Top 5 Peaks 194.0963 999 192.0806 273 193.0883 59 179.073 15 237.1021 11 102 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-5742023f1e263fb40066 splash10-0006-0900000000-5742023f1e263fb40066 102 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:273,193.0883:59,179.073:15,237.1021:11 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:273,193.0883:59,179.073:15,237.1021:11 image/svg 102 License CC BY 103 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019406 MSBNK-Eawag-EA019406 103 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 103 Instrument LTQ Orbitrap XL Thermo Scientific 103 Instrument Type LC-ESI-ITFT 103 MS Level MS2 103 Ionization Mode POSITIVE 103 Ionization ESI 103 Collision Energy 75 % (nominal) 103 Fragmentation Mode HCD 103 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 103 Retention Time 7.8 min 103 Precursor m/z 237.1022 103 Precursor Adduct [M+H]+ 103 Top 5 Peaks 194.0962 999 192.0807 342 193.0883 281 179.0727 125 165.0698 54 103 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-f27fb9d17b228cc328b8 splash10-0006-0900000000-f27fb9d17b228cc328b8 103 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0962:999,192.0807:342,193.0883:281,179.0727:125,165.0698:54 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0962:999,192.0807:342,193.0883:281,179.0727:125,165.0698:54 image/svg 103 License CC BY 104 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019407 MSBNK-Eawag-EA019407 104 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 104 Instrument LTQ Orbitrap XL Thermo Scientific 104 Instrument Type LC-ESI-ITFT 104 MS Level MS2 104 Ionization Mode POSITIVE 104 Ionization ESI 104 Collision Energy 90 % (nominal) 104 Fragmentation Mode HCD 104 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 104 Retention Time 7.8 min 104 Precursor m/z 237.1022 104 Precursor Adduct [M+H]+ 104 Top 5 Peaks 193.0884 999 194.0962 897 179.0728 538 192.0806 478 165.0697 253 104 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-63c554c485fd1d117082 splash10-0006-0900000000-63c554c485fd1d117082 104 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0884:999,194.0962:897,179.0728:538,192.0806:478,165.0697:253 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0884:999,194.0962:897,179.0728:538,192.0806:478,165.0697:253 image/svg 104 License CC BY 105 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019408 MSBNK-Eawag-EA019408 105 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 105 Instrument LTQ Orbitrap XL Thermo Scientific 105 Instrument Type LC-ESI-ITFT 105 MS Level MS2 105 Ionization Mode POSITIVE 105 Ionization ESI 105 Collision Energy 15 % (nominal) 105 Fragmentation Mode HCD 105 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 105 Retention Time 7.8 min 105 Precursor m/z 237.1022 105 Precursor Adduct [M+H]+ 105 Top 5 Peaks 237.1021 999 194.0961 25 192.0807 2 220.0751 1 105 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0090000000-c6c89d3e663885fcc080 splash10-000i-0090000000-c6c89d3e663885fcc080 105 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1021:999,194.0961:25,192.0807:2,220.0751:1, https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1021:999,194.0961:25,192.0807:2,220.0751:1, image/svg 105 License CC BY 106 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019409 MSBNK-Eawag-EA019409 106 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 106 Instrument LTQ Orbitrap XL Thermo Scientific 106 Instrument Type LC-ESI-ITFT 106 MS Level MS2 106 Ionization Mode POSITIVE 106 Ionization ESI 106 Collision Energy 30 % (nominal) 106 Fragmentation Mode HCD 106 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 106 Retention Time 7.8 min 106 Precursor m/z 237.1022 106 Precursor Adduct [M+H]+ 106 Top 5 Peaks 237.1022 999 194.0963 463 192.0806 64 220.0756 13 193.0884 7 106 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0490000000-8a1d8d7b932f1b0ad45e splash10-000i-0490000000-8a1d8d7b932f1b0ad45e 106 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0963:463,192.0806:64,220.0756:13,193.0884:7 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0963:463,192.0806:64,220.0756:13,193.0884:7 image/svg 106 License CC BY 107 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019410 MSBNK-Eawag-EA019410 107 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 107 Instrument LTQ Orbitrap XL Thermo Scientific 107 Instrument Type LC-ESI-ITFT 107 MS Level MS2 107 Ionization Mode POSITIVE 107 Ionization ESI 107 Collision Energy 45 % (nominal) 107 Fragmentation Mode HCD 107 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 107 Retention Time 7.8 min 107 Precursor m/z 237.1022 107 Precursor Adduct [M+H]+ 107 Top 5 Peaks 194.0963 999 192.0806 217 237.1019 173 193.0882 17 220.0757 6 107 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0910000000-843efaf5294cb110e0b9 splash10-0006-0910000000-843efaf5294cb110e0b9 107 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:217,237.1019:173,193.0882:17,220.0757:6 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:217,237.1019:173,193.0882:17,220.0757:6 image/svg 107 License CC BY 108 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019411 MSBNK-Eawag-EA019411 108 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 108 Instrument LTQ Orbitrap XL Thermo Scientific 108 Instrument Type LC-ESI-ITFT 108 MS Level MS2 108 Ionization Mode POSITIVE 108 Ionization ESI 108 Collision Energy 60 % (nominal) 108 Fragmentation Mode HCD 108 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 108 Retention Time 7.8 min 108 Precursor m/z 237.1022 108 Precursor Adduct [M+H]+ 108 Top 5 Peaks 194.0964 999 192.0807 261 193.0885 55 179.0728 13 167.0854 9 108 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-7eb2855f73a1ed729181 splash10-0006-0900000000-7eb2855f73a1ed729181 108 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,192.0807:261,193.0885:55,179.0728:13,167.0854:9 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,192.0807:261,193.0885:55,179.0728:13,167.0854:9 image/svg 108 License CC BY 109 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019412 MSBNK-Eawag-EA019412 109 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 109 Instrument LTQ Orbitrap XL Thermo Scientific 109 Instrument Type LC-ESI-ITFT 109 MS Level MS2 109 Ionization Mode POSITIVE 109 Ionization ESI 109 Collision Energy 75 % (nominal) 109 Fragmentation Mode HCD 109 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 109 Retention Time 7.8 min 109 Precursor m/z 237.1022 109 Precursor Adduct [M+H]+ 109 Top 5 Peaks 194.0963 999 192.0806 329 193.0884 267 179.0728 132 165.0696 50 109 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-8a4709b0e827021ff3f9 splash10-0006-0900000000-8a4709b0e827021ff3f9 109 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:329,193.0884:267,179.0728:132,165.0696:50 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0806:329,193.0884:267,179.0728:132,165.0696:50 image/svg 109 License CC BY 110 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019413 MSBNK-Eawag-EA019413 110 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 110 Instrument LTQ Orbitrap XL Thermo Scientific 110 Instrument Type LC-ESI-ITFT 110 MS Level MS2 110 Ionization Mode POSITIVE 110 Ionization ESI 110 Collision Energy 90 % (nominal) 110 Fragmentation Mode HCD 110 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 110 Retention Time 7.8 min 110 Precursor m/z 237.1022 110 Precursor Adduct [M+H]+ 110 Top 5 Peaks 193.0884 999 194.0962 878 179.0727 497 192.0805 466 165.0696 256 110 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-1df850c9bb30bdd7c2e8 splash10-0006-0900000000-1df850c9bb30bdd7c2e8 110 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0884:999,194.0962:878,179.0727:497,192.0805:466,165.0696:256 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0884:999,194.0962:878,179.0727:497,192.0805:466,165.0696:256 image/svg 110 License CC BY 111 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Eawag-EA019414 MSBNK-Eawag-EA019414 111 Authors Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag 111 Instrument LTQ Orbitrap XL Thermo Scientific 111 Instrument Type LC-ESI-ITFT 111 MS Level MS2 111 Ionization Mode POSITIVE 111 Ionization ESI 111 Collision Energy 35 % (nominal) 111 Fragmentation Mode CID 111 Column Name XBridge C18 3.5um, 2.1x50mm, Waters 111 Retention Time 7.8 min 111 Precursor m/z 237.1022 111 Precursor Adduct [M+H]+ 111 Top 5 Peaks 194.0963 999 220.0754 72 192.0806 45 179.0737 1 190.0652 1 111 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-13a692d2c13ee8b68c2b splash10-0006-0900000000-13a692d2c13ee8b68c2b 111 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,220.0754:72,192.0806:45,179.0737:1,190.0652:1 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,220.0754:72,192.0806:45,179.0737:1,190.0652:1 image/svg 111 License CC BY 112 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Fiocruz-FIO01104 MSBNK-Fiocruz-FIO01104 112 Authors Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil) 112 Instrument maXis (Bruker Daltonics) 112 Instrument Type LC-ESI-QTOF 112 MS Level MS2 112 Ionization Mode POSITIVE 112 Ionization ESI 112 Collision Energy 10 eV 112 Fragmentation Mode CID 112 Column Name Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm 112 Precursor Adduct [M+H]+ 112 Top 5 Peaks 237.1028 999 238.1058 153 194.0967 122 195.0999 17 192.0809 15 112 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0190000000-6940c1a4f622ea18fc1f splash10-000i-0190000000-6940c1a4f622ea18fc1f 112 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1028:999,238.1058:153,194.0967:122,195.0999:17,192.0809:15 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1028:999,238.1058:153,194.0967:122,195.0999:17,192.0809:15 image/svg 112 License CC BY 113 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Fiocruz-FIO01105 MSBNK-Fiocruz-FIO01105 113 Authors Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil) 113 Instrument maXis (Bruker Daltonics) 113 Instrument Type LC-ESI-QTOF 113 MS Level MS2 113 Ionization Mode POSITIVE 113 Ionization ESI 113 Collision Energy 20 eV 113 Fragmentation Mode CID 113 Column Name Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm 113 Precursor Adduct [M+H]+ 113 Top 5 Peaks 194.097 999 237.1028 231 192.0811 189 195.1002 151 193.0868 52 113 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0910000000-09656fac96a5c0f74c12 splash10-0006-0910000000-09656fac96a5c0f74c12 113 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.097:999,237.1028:231,192.0811:189,195.1002:151,193.0868:52 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.097:999,237.1028:231,192.0811:189,195.1002:151,193.0868:52 image/svg 113 License CC BY 114 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Fiocruz-FIO01106 MSBNK-Fiocruz-FIO01106 114 Authors Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil) 114 Instrument maXis (Bruker Daltonics) 114 Instrument Type LC-ESI-QTOF 114 MS Level MS2 114 Ionization Mode POSITIVE 114 Ionization ESI 114 Collision Energy 30 eV 114 Fragmentation Mode CID 114 Column Name Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm 114 Precursor Adduct [M+H]+ 114 Top 5 Peaks 194.0966 999 192.0809 296 193.0877 166 195.0998 151 179.0727 54 114 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-173c09c99cafa6f96149 splash10-0006-0900000000-173c09c99cafa6f96149 114 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0966:999,192.0809:296,193.0877:166,195.0998:151,179.0727:54 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0966:999,192.0809:296,193.0877:166,195.0998:151,179.0727:54 image/svg 114 License CC BY 115 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Fiocruz-FIO01107 MSBNK-Fiocruz-FIO01107 115 Authors Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil) 115 Instrument maXis (Bruker Daltonics) 115 Instrument Type LC-ESI-QTOF 115 MS Level MS2 115 Ionization Mode POSITIVE 115 Ionization ESI 115 Collision Energy 40 eV 115 Fragmentation Mode CID 115 Column Name Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm 115 Precursor Adduct [M+H]+ 115 Top 5 Peaks 194.096 999 193.0884 881 192.0804 554 179.0728 449 165.0696 246 115 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-ae291f3d9dae18d04868 splash10-0006-0900000000-ae291f3d9dae18d04868 115 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.096:999,193.0884:881,192.0804:554,179.0728:449,165.0696:246 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.096:999,193.0884:881,192.0804:554,179.0728:449,165.0696:246 image/svg 115 License CC BY 116 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Fiocruz-FIO01108 MSBNK-Fiocruz-FIO01108 116 Authors Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil) 116 Instrument maXis (Bruker Daltonics) 116 Instrument Type LC-ESI-QTOF 116 MS Level MS2 116 Ionization Mode POSITIVE 116 Ionization ESI 116 Collision Energy 50 eV 116 Fragmentation Mode CID 116 Column Name Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm 116 Precursor Adduct [M+H]+ 116 Top 5 Peaks 193.0883 999 192.0804 739 179.0726 569 165.0698 511 191.0728 495 116 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-cd8906ffc92d813ed7f1 splash10-0006-0900000000-cd8906ffc92d813ed7f1 116 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0883:999,192.0804:739,179.0726:569,165.0698:511,191.0728:495 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0883:999,192.0804:739,179.0726:569,165.0698:511,191.0728:495 image/svg 116 License CC BY 117 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-LCSB-LU126601 MSBNK-LCSB-LU126601 117 Authors Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E. 117 Instrument Q Exactive Orbitrap (Thermo Scientific) 117 Instrument Type LC-ESI-QFT 117 MS Level MS2 117 Ionization Mode POSITIVE 117 Ionization ESI 117 Collision Energy 15 117 Fragmentation Mode HCD 117 Column Name Acquity BEH C18 1.7um, 2.1x150mm (Waters) 117 Retention Time 15.734 min 117 Precursor m/z 237.1022 117 Precursor Adduct [M+H]+ 117 Top 5 Peaks 237.1022 999 194.0965 286 192.0808 23 220.0758 20 193.0887 2 117 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0290000000-7f5c6e0ed0ee141d98da splash10-000i-0290000000-7f5c6e0ed0ee141d98da 117 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0965:286,192.0808:23,220.0758:20,193.0887:2 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.1022:999,194.0965:286,192.0808:23,220.0758:20,193.0887:2 image/svg 117 License CC BY 117 Reference Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted). 118 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-LCSB-LU126602 MSBNK-LCSB-LU126602 118 Authors Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E. 118 Instrument Q Exactive Orbitrap (Thermo Scientific) 118 Instrument Type LC-ESI-QFT 118 MS Level MS2 118 Ionization Mode POSITIVE 118 Ionization ESI 118 Collision Energy 30 118 Fragmentation Mode HCD 118 Column Name Acquity BEH C18 1.7um, 2.1x150mm (Waters) 118 Retention Time 15.734 min 118 Precursor m/z 237.1022 118 Precursor Adduct [M+H]+ 118 Top 5 Peaks 194.0964 999 237.1022 634 192.0809 138 220.0757 38 193.0889 9 118 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000f-0950000000-504f38db6ace577bb59d splash10-000f-0950000000-504f38db6ace577bb59d 118 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,237.1022:634,192.0809:138,220.0757:38,193.0889:9 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,237.1022:634,192.0809:138,220.0757:38,193.0889:9 image/svg 118 License CC BY 118 Reference Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted). 119 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-LCSB-LU126603 MSBNK-LCSB-LU126603 119 Authors Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E. 119 Instrument Q Exactive Orbitrap (Thermo Scientific) 119 Instrument Type LC-ESI-QFT 119 MS Level MS2 119 Ionization Mode POSITIVE 119 Ionization ESI 119 Collision Energy 45 119 Fragmentation Mode HCD 119 Column Name Acquity BEH C18 1.7um, 2.1x150mm (Waters) 119 Retention Time 15.734 min 119 Precursor m/z 237.1022 119 Precursor Adduct [M+H]+ 119 Top 5 Peaks 194.0963 999 192.0809 220 237.1022 42 193.0888 25 220.0758 5 119 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-638bb2415e5fe50e8595 splash10-0006-0900000000-638bb2415e5fe50e8595 119 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0809:220,237.1022:42,193.0888:25,220.0758:5 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0809:220,237.1022:42,193.0888:25,220.0758:5 image/svg 119 License CC BY 119 Reference Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted). 120 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-LCSB-LU126604 MSBNK-LCSB-LU126604 120 Authors Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E. 120 Instrument Q Exactive Orbitrap (Thermo Scientific) 120 Instrument Type LC-ESI-QFT 120 MS Level MS2 120 Ionization Mode POSITIVE 120 Ionization ESI 120 Collision Energy 60 120 Fragmentation Mode HCD 120 Column Name Acquity BEH C18 1.7um, 2.1x150mm (Waters) 120 Retention Time 15.734 min 120 Precursor m/z 237.1022 120 Precursor Adduct [M+H]+ 120 Top 5 Peaks 194.0963 999 192.0809 286 193.0888 121 179.0729 49 167.0855 19 120 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-c9bce8ba5ddce151043c splash10-0006-0900000000-c9bce8ba5ddce151043c 120 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0809:286,193.0888:121,179.0729:49,167.0855:19 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0963:999,192.0809:286,193.0888:121,179.0729:49,167.0855:19 image/svg 120 License CC BY 120 Reference Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted). 121 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-LCSB-LU126605 MSBNK-LCSB-LU126605 121 Authors Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E. 121 Instrument Q Exactive Orbitrap (Thermo Scientific) 121 Instrument Type LC-ESI-QFT 121 MS Level MS2 121 Ionization Mode POSITIVE 121 Ionization ESI 121 Collision Energy 75 121 Fragmentation Mode HCD 121 Column Name Acquity BEH C18 1.7um, 2.1x150mm (Waters) 121 Retention Time 15.734 min 121 Precursor m/z 237.1022 121 Precursor Adduct [M+H]+ 121 Top 5 Peaks 194.0964 999 193.0888 598 192.081 411 179.073 295 165.07 152 121 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-3663be590fd2852b9b77 splash10-0006-0900000000-3663be590fd2852b9b77 121 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,193.0888:598,192.081:411,179.073:295,165.07:152 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,193.0888:598,192.081:411,179.073:295,165.07:152 image/svg 121 License CC BY 121 Reference Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted). 122 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-LCSB-LU126606 MSBNK-LCSB-LU126606 122 Authors Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E. 122 Instrument Q Exactive Orbitrap (Thermo Scientific) 122 Instrument Type LC-ESI-QFT 122 MS Level MS2 122 Ionization Mode POSITIVE 122 Ionization ESI 122 Collision Energy 90 122 Fragmentation Mode HCD 122 Column Name Acquity BEH C18 1.7um, 2.1x150mm (Waters) 122 Retention Time 15.734 min 122 Precursor m/z 237.1022 122 Precursor Adduct [M+H]+ 122 Top 5 Peaks 193.0886 999 179.0729 562 192.0809 449 194.0963 446 165.0699 367 122 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-ee4fac61627e460e668c splash10-0006-0900000000-ee4fac61627e460e668c 122 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0886:999,179.0729:562,192.0809:449,194.0963:446,165.0699:367 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=193.0886:999,179.0729:562,192.0809:449,194.0963:446,165.0699:367 image/svg 122 License CC BY 122 Reference Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted). 125 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-UFZ-WANA020411C9CFPH MSBNK-UFZ-WANA020411C9CFPH 125 Authors Tobias Schulze, Martin Krauss, Department of Effect-Directed Analysis, Helmholtz Centre for Environmental Research - UFZ, Leipzig, Germany 125 Instrument LTQ Orbitrap XL Thermo Scientific 125 Instrument Type LC-ESI-ITFT 125 MS Level MS2 125 Ionization Mode POSITIVE 125 Ionization ESI 125 Collision Energy 40 % (nominal) 125 Fragmentation Mode HCD 125 Column Name Kinetex Evo C18 2.6 um 50 x 2.1 mm 125 Retention Time 9.605 min 125 Precursor m/z 237.1022 125 Precursor Adduct [M+H]+ 125 Top 5 Peaks 194.0966 999 237.1025 404 192.0811 176 220.076 15 193.0889 10 125 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0930000000-597ead7ea9112a4dc120 splash10-0006-0930000000-597ead7ea9112a4dc120 125 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0966:999,237.1025:404,192.0811:176,220.076:15,193.0889:10 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0966:999,237.1025:404,192.0811:176,220.076:15,193.0889:10 image/svg 125 License CC0 126 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-UFZ-WANA020413D9F1PH MSBNK-UFZ-WANA020413D9F1PH 126 Authors Tobias Schulze, Martin Krauss, Department of Effect-Directed Analysis, Helmholtz Centre for Environmental Research - UFZ, Leipzig, Germany 126 Instrument LTQ Orbitrap XL Thermo Scientific 126 Instrument Type LC-ESI-ITFT 126 MS Level MS2 126 Ionization Mode POSITIVE 126 Ionization ESI 126 Collision Energy 50 % (nominal) 126 Fragmentation Mode HCD 126 Column Name Kinetex Evo C18 2.6 um 50 x 2.1 mm 126 Retention Time 9.605 min 126 Precursor m/z 237.1022 126 Precursor Adduct [M+H]+ 126 Top 5 Peaks 194.0966 999 192.0812 229 237.1026 86 193.089 18 220.0759 5 126 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-a8f2462ab5217dbb2234 splash10-0006-0900000000-a8f2462ab5217dbb2234 126 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0966:999,192.0812:229,237.1026:86,193.089:18,220.0759:5 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0966:999,192.0812:229,237.1026:86,193.089:18,220.0759:5 image/svg 126 License CC0 127 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-UFZ-WANA0204155BE0PH MSBNK-UFZ-WANA0204155BE0PH 127 Authors Tobias Schulze, Martin Krauss, Department of Effect-Directed Analysis, Helmholtz Centre for Environmental Research - UFZ, Leipzig, Germany 127 Instrument LTQ Orbitrap XL Thermo Scientific 127 Instrument Type LC-ESI-ITFT 127 MS Level MS2 127 Ionization Mode POSITIVE 127 Ionization ESI 127 Collision Energy 60 % (nominal) 127 Fragmentation Mode HCD 127 Column Name Kinetex Evo C18 2.6 um 50 x 2.1 mm 127 Retention Time 9.605 min 127 Precursor m/z 237.1022 127 Precursor Adduct [M+H]+ 127 Top 5 Peaks 194.097 999 192.0816 265 193.0894 46 237.1031 12 167.0861 10 127 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-d1acd24cb408df7f5190 splash10-0006-0900000000-d1acd24cb408df7f5190 127 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.097:999,192.0816:265,193.0894:46,237.1031:12,167.0861:10 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.097:999,192.0816:265,193.0894:46,237.1031:12,167.0861:10 image/svg 127 License CC0 128 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Waters-WA001146 MSBNK-Waters-WA001146 128 Authors Nihon Waters K.K. 128 Instrument ZQ, Waters 128 Instrument Type LC-ESI-Q 128 MS Level MS 128 Ionization Mode POSITIVE 128 Ionization ESI 128 Column Name 2.1 mm id - 3. 5{mu}m XTerra C18MS 128 Retention Time 14.700 min 128 Top 5 Peaks 194 999 193 474 192 388 179 215 165 137 128 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-91693360c7d0921cf8c2 splash10-0006-0900000000-91693360c7d0921cf8c2 128 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:999,193:474,192:388,179:215,165:137 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:999,193:474,192:388,179:215,165:137 image/svg 128 License CC BY-NC 129 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Waters-WA001147 MSBNK-Waters-WA001147 129 Authors Nihon Waters K.K. 129 Instrument ZQ, Waters 129 Instrument Type LC-ESI-Q 129 MS Level MS 129 Ionization Mode POSITIVE 129 Ionization ESI 129 Column Name 2.1 mm id - 3. 5{mu}m XTerra C18MS 129 Retention Time 14.700 min 129 Top 5 Peaks 194 999 192 278 195 137 193 98 237 51 129 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-336ec83800d5a740417d splash10-0006-0900000000-336ec83800d5a740417d 129 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:999,192:278,195:137,193:98,237:51 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:999,192:278,195:137,193:98,237:51 image/svg 129 License CC BY-NC 130 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Waters-WA001148 MSBNK-Waters-WA001148 130 Authors Nihon Waters K.K. 130 Instrument ZQ, Waters 130 Instrument Type LC-ESI-Q 130 MS Level MS 130 Ionization Mode POSITIVE 130 Ionization ESI 130 Column Name 2.1 mm id - 3. 5{mu}m XTerra C18MS 130 Retention Time 14.700 min 130 Top 5 Peaks 194 999 237 611 192 172 195 125 259 125 130 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000f-0950000000-12b19be8388337c4471b splash10-000f-0950000000-12b19be8388337c4471b 130 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:999,237:611,192:172,195:125,259:125 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:999,237:611,192:172,195:125,259:125 image/svg 130 License CC BY-NC 131 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Waters-WA001149 MSBNK-Waters-WA001149 131 Authors Nihon Waters K.K. 131 Instrument ZQ, Waters 131 Instrument Type LC-ESI-Q 131 MS Level MS 131 Ionization Mode POSITIVE 131 Ionization ESI 131 Column Name 2.1 mm id - 3. 5{mu}m XTerra C18MS 131 Retention Time 14.700 min 131 Top 5 Peaks 237 999 238 145 194 118 259 67 195 16 131 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0190000000-21bf9ce95f1d326d538f splash10-000i-0190000000-21bf9ce95f1d326d538f 131 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:999,238:145,194:118,259:67,195:16 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:999,238:145,194:118,259:67,195:16 image/svg 131 License CC BY-NC 132 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-Waters-WA001150 MSBNK-Waters-WA001150 132 Authors Nihon Waters K.K. 132 Instrument ZQ, Waters 132 Instrument Type LC-ESI-Q 132 MS Level MS 132 Ionization Mode POSITIVE 132 Ionization ESI 132 Column Name 2.1 mm id - 3. 5{mu}m XTerra C18MS 132 Retention Time 14.700 min 132 Top 5 Peaks 237 999 473 196 238 145 495 67 474 59 132 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000i-0090200000-341301de4b6398978020 splash10-000i-0090200000-341301de4b6398978020 132 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:999,473:196,238:145,495:67,474:59 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:999,473:196,238:145,495:67,474:59 image/svg 132 License CC BY-NC 133 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/WA001150 WA001150 133 MS Category Experimental 133 MS Type LC-MS 133 MS Level MS1 133 Instrument ZQ, Waters 133 Instrument Type LC-ESI-Q 133 Ionization ESI 133 Ionization Mode positive 133 Retention Time 14.700 min 133 Top 5 Peaks 237 100 473 19.62 238 14.51 495 6.71 474 5.91 133 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-000i-0090200000-341301de4b6398978020%27) splash10-000i-0090200000-341301de4b6398978020 133 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:100,473:19.62,238:14.51,495:6.71,474:5.91 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:100,473:19.62,238:14.51,495:6.71,474:5.91 image/svg 133 License CC BY-NC 134 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/WA001149 WA001149 134 MS Category Experimental 134 MS Type LC-MS 134 MS Level MS1 134 Instrument ZQ, Waters 134 Instrument Type LC-ESI-Q 134 Ionization ESI 134 Ionization Mode positive 134 Retention Time 14.700 min 134 Top 5 Peaks 237 100 238 14.51 194 11.81 259 6.71 195 1.60 134 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-000i-0190000000-21bf9ce95f1d326d538f%27) splash10-000i-0190000000-21bf9ce95f1d326d538f 134 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:100,238:14.51,194:11.81,259:6.71,195:1.60 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237:100,238:14.51,194:11.81,259:6.71,195:1.60 image/svg 134 License CC BY-NC 135 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/WA001148 WA001148 135 MS Category Experimental 135 MS Type LC-MS 135 MS Level MS1 135 Instrument ZQ, Waters 135 Instrument Type LC-ESI-Q 135 Ionization ESI 135 Ionization Mode positive 135 Retention Time 14.700 min 135 Top 5 Peaks 194 100 237 61.16 192 17.22 259 12.51 195 12.51 135 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-000f-0950000000-12b19be8388337c4471b%27) splash10-000f-0950000000-12b19be8388337c4471b 135 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:100,237:61.16,192:17.22,259:12.51,195:12.51 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194:100,237:61.16,192:17.22,259:12.51,195:12.51 image/svg 135 License CC BY-NC

Other MS This section provides this compound's mass spectrometry (MS) information that is not shown in other sections. ThisSection 2 Name Value 2 59 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V3: 2458 MASS: 42308 (NIST/EPA/MSDC Mass Spectral Database, 1990 version) 22 4 https://pubchem.ncbi.nlm.nih.gov/compound/MSDC PubChem Internal Link CID-131526 74 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-ACES_SU-AS000089 MSBNK-ACES_SU-AS000089 74 Authors ACESx, Jonathan W. Martin Group 74 Instrument QExactive Orbitrap HF-X (Thermo Scientific) 74 Instrument Type LC-APCI-QFT 74 MS Level MS2 74 Ionization Mode POSITIVE 74 Ionization APCI 74 Collision Energy Ramp 20%-70% (nominal) 74 Fragmentation Mode HCD 74 Column Name Waters; Acquity UPLC BEH C18, 2.1 x 100 mm, 1.7 um, Waters 74 Retention Time 13.8553 74 Precursor m/z 237.1023 74 Top 5 Peaks 237.10187 999 194.09666 795 192.08133 213 193.08847 187 179.07304 83 74 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-000f-0960000000-a3033693b0019d1b04c5 splash10-000f-0960000000-a3033693b0019d1b04c5 74 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.10187:999,194.09666:795,192.08133:213,193.08847:187,179.07304:83 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=237.10187:999,194.09666:795,192.08133:213,193.08847:187,179.07304:83 image/svg 74 License CC BY 123 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-UFZ-UA003001 MSBNK-UFZ-UA003001 123 Authors C. Gallampois (Umea), E. Schymanski (Eawag), W. Brack (UFZ) 123 Instrument LTQ Orbitrap XL Thermo Scientific 123 Instrument Type ESI-ITFT 123 MS Level MS2 123 Ionization Mode POSITIVE 123 Ionization ESI 123 Collision Energy 35 % (nominal) 123 Fragmentation Mode CID 123 Precursor m/z 237.1022 123 Precursor Adduct [M+H]+ 123 Top 5 Peaks 194.0965 999 220.076 68 192.0811 61 193.0886 2 123 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-ff23826da10bdf95f991 splash10-0006-0900000000-ff23826da10bdf95f991 123 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0965:999,220.076:68,192.0811:61,193.0886:2, https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0965:999,220.076:68,192.0811:61,193.0886:2, image/svg 123 License CC BY 123 Reference Multi-criteria approach for tentative identification of polyaromatic river mutagens 124 Accession ID https://massbank.eu/MassBank/RecordDisplay?id=MSBNK-UFZ-UA003003 MSBNK-UFZ-UA003003 124 Authors C. Gallampois (Umea), E. Schymanski (Eawag), W. Brack (UFZ) 124 Instrument LTQ Orbitrap XL Thermo Scientific 124 Instrument Type APCI-ITFT 124 MS Level MS2 124 Ionization Mode POSITIVE 124 Ionization APCI 124 Collision Energy 35 % (nominal) 124 Fragmentation Mode CID 124 Precursor m/z 237.1022 124 Precursor Adduct [M+H]+ 124 Top 5 Peaks 194.0964 999 220.0754 71 192.0809 57 193.0884 2 124 SPLASH https://massbank.eu/MassBank/Result.jsp?splash=splash10-0006-0900000000-25b86b23833bee39c759 splash10-0006-0900000000-25b86b23833bee39c759 124 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,220.0754:71,192.0809:57,193.0884:2, https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=194.0964:999,220.0754:71,192.0809:57,193.0884:2, image/svg 124 License CC BY 124 Reference Multi-criteria approach for tentative identification of polyaromatic river mutagens 136 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/LibGen000211 LibGen000211 136 MS Category Experimental 136 MS Type Other 136 MS Level MS2 136 Precursor Type [M+H]+ 136 Precursor m/z 237.1022395 136 Ionization Mode positive 136 Retention Time 3.698001074745085 136 Top 5 Peaks 168.08920851198226 9.22 61.001272511982265 9.02 98.01848051198226 8.51 123.02788551198226 7.60 96.99905351198227 6.28 136 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-02i2-9400000000-daae65b440a1f7f40954%27) splash10-02i2-9400000000-daae65b440a1f7f40954 136 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=168.08920851198226:9.22,61.001272511982265:9.02,98.01848051198226:8.51,123.02788551198226:7.60,96.99905351198227:6.28 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=168.08920851198226:9.22,61.001272511982265:9.02,98.01848051198226:8.51,123.02788551198226:7.60,96.99905351198227:6.28 image/svg 137 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/LibGen000165 LibGen000165 137 MS Category Experimental 137 MS Type Other 137 MS Level MS2 137 Precursor Type [M+Cl]- 137 Precursor m/z 271.064365 137 Ionization Mode negative 137 Retention Time 4.228820377962419 137 Top 5 Peaks 214.040916358205 0.30 243.0820270578224 0.28 213.032620358205 0.16 186.04217697539806 0.13 141.04044316313488 0.05 137 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-03dl-0290000000-3f0ac854181f0a205dbd%27) splash10-03dl-0290000000-3f0ac854181f0a205dbd 137 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=214.040916358205:0.30,243.0820270578224:0.28,213.032620358205:0.16,186.04217697539806:0.13,141.04044316313488:0.05 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=214.040916358205:0.30,243.0820270578224:0.28,213.032620358205:0.16,186.04217697539806:0.13,141.04044316313488:0.05 image/svg 138 MoNA ID https://mona.fiehnlab.ucdavis.edu/spectra/display/LibGen000164 LibGen000164 138 MS Category Experimental 138 MS Type Other 138 MS Level MS2 138 Precursor Type [M+Cl]- 138 Precursor m/z 271.064365 138 Ionization Mode negative 138 Retention Time 2.5827401752613794 138 Top 5 Peaks 214.04245871856634 0.30 243.08458256204548 0.25 213.03443771856632 0.15 186.0436395442502 0.10 141.04058146123268 0.04 138 SPLASH https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(splash.splash:%27splash10-03dl-0390000000-0eba4c9ff036957ba03f%27) splash10-03dl-0390000000-0eba4c9ff036957ba03f 138 Thumbnail https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=214.04245871856634:0.30,243.08458256204548:0.25,213.03443771856632:0.15,186.0436395442502:0.10,141.04058146123268:0.04 https://pubchem.ncbi.nlm.nih.gov/image/ms.cgi?peaks=214.04245871856634:0.30,243.08458256204548:0.25,213.03443771856632:0.15,186.0436395442502:0.10,141.04058146123268:0.04 image/svg

UV Spectra Ultraviolet (UV) spectroscopy (or Spectrophotometry) is an analytical technique used to measure how much a molecule absorbs light in the ultraviolet spectral region. This technique is particularly useful to study aromatic, conjugated, and other substances containing a pi bond. Modern ultraviolet spectrophotometers also cover the visible light range, in which case the technique is called ultraviolet-visible (UV-Vis) spectroscopy. https://chem.libretexts.org/Courses/Brevard_College/CHE_202%3A_Organic_Chemistry_II/05%3A_Structural__Determination_I/5.05%3A_Ultraviolet_and_visible_spectroscopy 59 PEER REVIEWED Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V3: 2458 UV: 1277 (Absorption Spectra in the UV and visible Regions, Academic Press, New York)

IR Spectra Infrared spectroscopy (IR spectroscopy) is the spectroscopy that deals with the infrared region of the electromagnetic spectrum extending from 780 nm to about 20000 nm. The IR spectra tells you what types of vibrational mode (motion) responses occur in a molecule interacting with infrared light. It is used to help determine the functional groups in a molecule. https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Spectroscopy/Vibrational_Spectroscopy/Infrared_Spectroscopy ThisSection 2 Name Value 2

FTIR Spectra Fourier transform infrared spectroscopy (FTIR) results for this chemical. https://chem.libretexts.org/Courses/Howard_University/Howard%3A_Physical_Chemistry_Laboratory/14._Fourier_Transform_Infrared_Spectroscopy_(FTIR) ThisSection 2 Name Value 2 171 Technique KBr WAFER 171 Source of Sample Geigy Chemical Corporation 171 Copyright Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved. 171 Thumbnail https://spectrabase.com/spectrum/FbF3qV5CBf4 https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4772154_1 image/png 175 Technique Mull 175 Source of Spectrum Sigma-Aldrich Co. LLC. 175 Source of Sample Aldrich 175 Catalog Number 309486 175 Copyright Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved. 175 Thumbnail https://spectrabase.com/spectrum/DUpOUnYt8os https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/10098225_1 image/png

ATR-IR Spectra Attenuated total reflection infrared (ATR-IR) spectral data. ATR is a sampling technique that enables samples to be examined directly in the solid or liquid state without further preparation. ATR-IR can be applied to the same chemical or biological systems as the transmission IR. An advantage of ATR-IR over the transmission IR is the limited path length into the sample, because ATR-IR avoids the problem of strong attenuation of the IR signal in highly absorbing media such as aqueous solutions. https://chem.libretexts.org/Bookshelves/Analytical_Chemistry/Supplemental_Modules_(Analytical_Chemistry)/Instrumental_Analysis/Spectrometer/ATR-FTIR ThisSection 2 Name Value 2 170 Instrument Name Bio-Rad FTS 170 Technique ATR-Neat (DuraSamplIR II) 170 Source of Spectrum Forensic Spectral Research 170 Source of Sample Alltech Associates, Inc., Grace Davison Discovery Sciences 170 Catalog Number 01788 170 Lot Number 101 170 Copyright Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved. 170 Thumbnail https://spectrabase.com/spectrum/nvsudQ4SuY https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4772153_1 image/png 174 Source of Sample Aldrich 174 Catalog Number 309486 174 Copyright Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved. 174 Thumbnail https://spectrabase.com/spectrum/LECFCRnUnNo https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/10098224_1 image/png

Raman Spectra Raman spectroscopy is a spectroscopic technique typically used to study vibrational modes of a molecular system, although it can also be used to observe rotational and other low-frequency modes of the system. Raman spectroscopy is based on inelastic scattering of photons, known as Raman scattering. https://chem.libretexts.org/Bookshelves/Analytical_Chemistry/Map%3A_Principles_of_Instrumental_Analysis_(Skoog_et_al.)/18%3A_Raman_Spectroscopy ThisSection 2 Name Value 2 172 Technique FT-Raman 172 Source of Spectrum Forensic Spectral Research 172 Source of Sample Alltech Associates, Inc., Grace Davison Discovery Sciences 172 Catalog Number 01788 172 Lot Number 101 172 Copyright Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved. 172 Thumbnail https://spectrabase.com/spectrum/FsfunOsZ6UX https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/4772155_1 image/png

Other Spectra Spectral information for this compound that is not shown in other sections. 59 PEER REVIEWED Pfleger, K., H. Maurer and A. Weber. Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Parts I and II. Mass Spectra Indexes. Weinheim, Federal Republic of Germany. 1985., p. 388 Intense mass spectral peaks: 165 m/z, 193 m/z, 236 m/z

Related Records Records related to this compound. This includes PubChem compound and substance records, as well as records in NCBI resources (e.g., PubMed, Gene, Protein Structure, and Taxonomy) and other databases external to NCBI.

Related Compounds with Annotation Compound records that are closely related to this record AND that have biomedical annotations. In essence, they are a subset of the compounds included in the "Related Compounds" section below this section. The "Related Compounds" include the parent, components, mixtures, and salt forms of this compound record as well as the "similar compounds" and "similar conformers", which are structurally similar to this record in terms of 2-D and 3-D chemical structure similarity measures, respectively, as explained in Kim et al., J. Cheminform. 2016, 8, 62. https://doi.org/10.1186/s13321-016-0163-1 199 true

Related Compounds Compound records closely related to this record. It includes compounds which are the parent, components, mixtures, and salt forms of this compound record. It also includes the "similar compounds" and "similar conformers", which are structurally similar to this record in terms of 2-D and 3-D chemical structure similarity measures, respectively, as explained in Kim et al., J. Cheminform. 2016, 8, 62. https://doi.org/10.1186/s13321-016-0163-1 ThisSection 2 Name Value 1 199 Same Connectivity Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/cids/JSON?cids_type=same_connectivity&list_return=redirect 12 199 Same Parent, Connectivity Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/cids/JSON?cids_type=same_parent_connectivity&list_return=redirect 45 199 Same Parent, Exact Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/cids/JSON?cids_type=same_parent&list_return=redirect 33 199 Mixtures, Components, and Neutralized Forms Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/cids/JSON?cids_type=component&list_return=redirect 143 199 Similar Compounds Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/cids/JSON?cids_type=similar_2d&list_return=redirect 194 199 Similar Conformers Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/cids/JSON?cids_type=similar_3d&list_return=redirect 1167

Substances Substance records associated with this compound. In PubChem, the term "substance" refers to depositor-provided data for a chemical.. https://pubchem.ncbi.nlm.nih.gov/docs/substances

PubChem Reference Collection SID Substances from the special PubChem Reference Collection associated with this compound. true 199 https://pubchem.ncbi.nlm.nih.gov/substance/481106986 481106986

Related Substances Substance records related to this compound (e.g., the standardized chemical structures of these substances are the same as this compound or correspond to a mixture containing this compound as a component). ThisSection 2 Name Value 1 199 All Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/sids/JSON?sids_type=all&list_return=redirect 608 199 Same Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/sids/JSON?sids_type=standardized&list_return=redirect 393 199 Mixture Count https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/sids/JSON?sids_type=component&list_return=redirect 215

Substances by Category Substances associated with this compound, grouped by the category of the data sources who submitted the substances to PubChem (e.g., government organizations, chemical vendors, research and development, curation efforts, NIH initiatives, etc.). 199 Chemical Vendors Curation Efforts Governmental Organizations Journal Publishers Legacy Depositors NIH Initiatives Research and Development Subscription Services

Entrez Crosslinks Cross-references to associated records in other Entrez databases such as PubMed, Gene, Protein, etc. ThisSection 2 Name Value 1 199 PubMed Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_pubmed&db=pccompound&cmd=Link&from_uid=2554 6894 199 Protein Structures Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_structure&db=pccompound&cmd=Link&from_uid=2554 2 199 Taxonomy Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_taxonomy&db=pccompound&cmd=Link&from_uid=2554 10 199 OMIM Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_omim&db=pccompound&cmd=Link&from_uid=2554 95 199 Gene Count https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_gene&db=pccompound&cmd=Link&from_uid=2554 2231

NCBI LinkOut NCBI LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyond NCBI systems. https://www.ncbi.nlm.nih.gov/projects/linkout/ 231 true

Chemical Vendors A list of chemical vendors that sell this compound. Note that the order of chemical vendors on the list is randomized, and that PubChem do not endorse any of the vendors. Each vendor may have multiple products containing the same chemical, but different in various aspects, such as amount and purity. For each product, the external identifier used to locate the product on the vendor's website is provided under the Purchasable Chemical column, and clicking this identifier directs you to the vendor's website. The information on the product provided by the vendor to PubChem can be accessed at the Summary page of the corresponding PubChem Substance ID (SID). 199 true

Drug and Medication Information This section provides drug and medication information for this compound, including drug indications, labeling, clinical trials, idiosyncrasies, tolerance, reported fatal doses, etc.

Drug Indication A drug indication refers to any valid reason (e.g., signs/symptoms or diseases/disorders) to use a certain drug. Many indications are label indications, approved by a regulatory agency (e.g., the U.S. Food and Drug Administration or European Medical Agency), meaning that the manufacturer is allowed to market the drug for the approved indications. However, some indications are not approved, and therefore, they are called off-label indications. This section may include both label indications and off-label indications. 3 30 Carbamazepine is indicated for the treatment of epilepsy and pain associated with true trigeminal neuralgia. In particular, carbamazepine has shown efficacy in treating mixed seizures, partial seizures with complex symptoms, and generalized tonic-clonic seizures. Carbamazepine is also indicated for the treatment of manic episodes and mixed manic-depressive episodes caused by bipolar I disorder. Some off-label, unapproved uses of carbamazepine include the treatment of alcohol withdrawal syndrome and restless leg syndrome. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 124 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 264 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 433 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 30 http://s3-us-west-2.amazonaws.com/drugbank/fda_labels/DB00564.pdf?1265922800 FDA Label

LiverTox Summary Summary of liver toxicity for this compound, provided by LiverTox. This section provides an overview of drug induced liver injury, diagnostic criteria, assessment of causality and severity, descriptions of different clinical patterns (phenotypes), information on management and treatment, and standardized nomenclature. The role of liver biopsy and major histological patterns of drug induced liver disease are also given. https://www.ncbi.nlm.nih.gov/books/NBK547852/ 73 Carbamazepine is an aromatic anticonvulsant that is widely used in therapy of epilepsy and trigeminal neuralgia and is a well established cause of clinically apparent liver injury which can be severe and even fatal. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Drug Classes Drug classes of this compound, based on its therapeutic uses and/or structure. The data presented in this section is from LiverTox. https://pubchem.ncbi.nlm.nih.gov/source/15404 73 Anticonvulsants

Drug Transformations This section provides information how a drug may be chemically transformed (in vivo or in the environment), such as by acetylation, oxidation, hydrogenation, etc. 163 S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448 Carbamazepine has known transformation products that include Carbamazepine-10,11-epoxide, Carbamazepine-10,11-dihydro-10,11-dihydroxy, and Iminostilbene. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 61 27 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 90 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 139 13 https://pubchem.ncbi.nlm.nih.gov/compound/Iminostilbene PubChem Internal Link CID-9212

FDA Medication Guides FDA Medication Guides are paper handouts that come with many prescription medicines. The guides address issues that are specific to particular drugs and drug classes, and they contain FDA-approved information that can help patients avoid serious adverse events. https://www.fda.gov/drugs/drug-safety-and-availability/medication-guides ThisSection 5 Drug Active Ingredient Form;Route Company Date true 3 51 Drug Carbatrol 0 9 https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/020712s038lbl.pdf#page=23 51 Active Ingredient Carbamazepine 51 Form;Route CAPSULE, EXTENDED RELEASE;ORAL 51 Company TAKEDA PHARMS USA 51 Date 04/11/2023 52 Drug Equetro 0 7 https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/021710s018lbl.pdf#page=27 52 Active Ingredient Carbamazepine 52 Form;Route CAPSULE, EXTENDED RELEASE;ORAL 52 Company VALIDUS PHARMS 52 Date 10/14/2022 53 Drug Tegretol 0 8 http://www.accessdata.fda.gov/drugsatfda_docs/label/2023/016608s121_018927s60_020234s054lbl.pdf#page=19 Tegretol 0 8 https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/016608s115_018281_s058_018927s055_020234_s047.pdf#page=19 Tegretol 0 8 http://www.accessdata.fda.gov/drugsatfda_docs/label/2023/016608s121_018927s60_020234s054lbl.pdf#page=19 53 Active Ingredient Carbamazepine Carbamazepine Carbamazepine 53 Form;Route SUSPENSION;ORAL TABLET, CHEWABLE;ORAL TABLET;ORAL 53 Company NOVARTIS NOVARTIS NOVARTIS 53 Date 09/13/2023 03/20/2018 09/13/2023 54 Drug Tegretol-XR 0 11 http://www.accessdata.fda.gov/drugsatfda_docs/label/2023/016608s121_018927s60_020234s054lbl.pdf#page=19 54 Active Ingredient Carbamazepine 54 Form;Route TABLET, EXTENDED RELEASE;ORAL 54 Company NOVARTIS 54 Date 09/13/2023

WHO Essential Medicines The WHO Essential Medicines present a list of minimum medicine needs for a basic health-care system, listing the most efficacious, safe and cost-effective medicines for priority conditions. https://www.who.int/groups/expert-committee-on-selection-and-use-of-essential-medicines/essential-medicines-lists ThisSection 4 Drug Drug Classes Formulation Indication true 3 193 Drug Carbamazepine 0 13 https://list.essentialmeds.org/medicines/49 Carbamazepine 0 13 https://list.essentialmeds.org/medicines/49 193 Drug Classes Antiseizure medicines Medicines for bipolar disorders 193 Formulation (1) Oral - Liquid: 100 mg per 5 mL; (2) Oral - Solid - tablet: 200 mg (scored); 100 mg (scored); 100 mg (chewable); 200 mg (chewable); 400 mg (scored) Oral - Solid - tablet: 100 mg (scored); 200 mg (scored); 400 mg 193 Indication Epilepsy or seizures [co-prescribed with N03AF01] Bipolar or related disorders [co-prescribed with N03AF01]

FDA Approved Drugs Drugs@FDA includes information about approved drugs and biological products for human use in the United States. https://www.fda.gov/drugs/drug-approvals-and-databases/about-drugsfda 32 collection=fdadrug&query_type=synonym&query='^EPITOL$' 33 collection=fdadrug&query_type=synonym&query='^CARBAMAZEPINE$' 34 collection=fdadrug&query_type=synonym&query='^TEGRETOL$'

FDA Orange Book The Orange Book identifies drug products approved on the basis of safety and effectiveness by the U.S. Food and Drug Administration (FDA) under the Federal Food, Drug, and Cosmetic Act and and related patent and exclusivity information. https://www.fda.gov/drugs/drug-approvals-and-databases/approved-drug-products-therapeutic-equivalence-evaluations-orange-book 55 collection=fdaorangebook&query_type=synonym&query='^CARBAMAZEPINE$' 56 collection=fdaorangebook&query_type=synonym&query='^EPITOL$' 57 collection=fdaorangebook&query_type=synonym&query='^TEGRETOL$'

FDA National Drug Code Directory The National Drug Code (NDC) is a unique product identifier in three-segment number used in the United States for human drugs (the Drug Listing Act of 1972). https://www.fda.gov/drugs/drug-approvals-and-databases/national-drug-code-directory 141 collection=fdandc&query_type=synonym&query='^TEGRETOL$' 142 collection=fdandc&query_type=synonym&query='^CARBAMAZEPINE$' 143 collection=fdandc&query_type=synonym&query='^EPITOL$'

Drug Labels This section provides the drug labeling information for drug products associated with this compound. This information is from The National Library of Medicine (NLM)'s DailyMed, which provides the most recent labeling submitted to the Food and Drug Administration (FDA) by companies and currently in use (i.e., "in use" labeling). DailyMed contains labeling for prescription and nonprescription drugs for human and animal use, and for additional products such as medical gases, devices, cosmetics, dietary supplements, and medical foods. https://dailymed.nlm.nih.gov/dailymed/ 27 Drug and label collection=dailymed&query_type=synonym&query='^CARBAMAZEPINE$' 27 Active ingredient and drug collection=dailymed_i&query_type=synonym&query='^CARBAMAZEPINE$'

Clinical Trials Clinical trials are research studies performed in people to evaluate a medical, surgical, or behavioral intervention. They are the primary way that researchers find out if a new treatment (e.g., a drug or diet) or medical device (e.g., a pacemaker) is safe and effective in people. This section provides information on clinical trials for this chemical.

ClinicalTrials.gov Brief clinical trials summary from ClinicalTrials.gov at the U.S. National Library of Medicine. http://clinicaltrials.gov/ 11 ClinicalTrials.gov clinicaltrials 80

EU Clinical Trials Register Brief clinical trials summary from the EU Clinical Trials Register. https://www.clinicaltrialsregister.eu/ 47 EU Clinical Trials Register clinicaltrials_eu 21

NIPH Clinical Trials Search of Japan Brief clinical trials summary from the NIPH Clinical Trials Search of Japan, which allows one to cross-search four national clinical research information registries in Japan: the Japan Registry of Clinical Trials (JRCT), the University Hospital Medical Information Network Center (UMIN-CTR), the Japan Pharmaceutical Information Center (JAPIC), and the Japan Medical Association Center for Clinical Trials (JMACCT). https://rctportal.niph.go.jp/en/ 148 NIPH Clinical Trials Search of Japan clinicaltrials_jp 1

Therapeutic Uses Therapeutic uses information for this compound, provided by the Hazardous Substances Data Bank (HSDB). https://pubchem.ncbi.nlm.nih.gov/source/11933 59 PEER REVIEWED National Library of Medicine's Medical Subject Headings online file (MeSH, 1999) Analgesics, Non-Narcotic; Anticonvulsants 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Carbamazepine has been shown to be effective in certain psychiatric disorders including schizoaffective illness, resistant schizophrenia, and dyscontrol syndrome, associated with limbic system dysfunction. /NOT included in US or Canadian product labeling/ 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Carbamazepine is used for the detoxification of alcoholics. It has been found to be effective in rapidly relieving anxiety and distress of acute alcohol withdrawal and for such symptoms as seizures, hyperexcitability, and sleep disturbances. /NOT included in US product labeling/ 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Carbamazepine is used alone or with other agents such as clofibrate or chlorpropamide in the treatment of partial central diabetes insipidus. /NOT included in US or Canadian product labeling/ 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 57 10 https://pubchem.ncbi.nlm.nih.gov/compound/clofibrate PubChem Internal Link CID-2796 71 14 https://pubchem.ncbi.nlm.nih.gov/compound/chlorpropamide PubChem Internal Link CID-2727 59 PEER REVIEWED For more Therapeutic Uses (Complete) data for CARBAMAZEPINE (10 total), please visit the HSDB record page. 89 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Therapeutic-Uses-(Complete) 46 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Drug Warnings Drug warnings information collected by the Hazardous Substances Data Bank (HSDB) from various sources, including US Pharmacopeia (USP), physicians desk references, MSDS, etc. https://pubchem.ncbi.nlm.nih.gov/source/11933 59 PEER REVIEWED McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2223 There have been a few cases of seizures and/or respiratory depression in neonates born to women receiving carbamazepine concomitantly with other anticonvulsant agents. A few cases of vomiting, diarrhea, and/or decreased feeding also have been reported in neonates born to women receiving carbamazepine; these symptoms may represent a neonatal withdrawal syndrome 106 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 288 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Carbamazepine should not be used prophylactically during long periods of remission in trigeminal neuralgia. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Although carbamazepine has ... been reported to relieve dystonic attacks in children, reduce migraine attacks, and relieve intractable hiccups in some patients, its therapeutic efficacy in such cases has not been established. 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Carbamazepine is not indicated for atypical or generalized absence seizures (petit mal) or myoclonic or atonic seizures. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Drug Warnings (Complete) data for CARBAMAZEPINE (30 total), please visit the HSDB record page. 86 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Drug-Warnings-(Complete) 43 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Pharmacology and Biochemistry Pharmacology and biochemistry information related to this compound, including the pharmacodynamics, pharmacokinetics, metabolism, mechanism of action, biological half-life, biochemical reactions, and many others.

Pharmacodynamics Pharmacodynamic information for this compound as a drug (i.e., what does this drug do to the body). Pharmacodynamics is the study of the biochemical, physiologic, and molecular effects of drugs on the body. https://www.ncbi.nlm.nih.gov/books/NBK507791/ 30 **General effects** Carbamazepine treats seizures and the symptoms of trigeminal neuralgia by inhibiting sodium channels. In bipolar 1 disorder, carbamazepine has been found to decrease mania symptoms in a clinically significant manner according to the Young Mania Rating Scale (YMRS). Carbamazepine has a narrow therapeutic index. **A note on genetic variation and carbamazepine use** In studies of Han Chinese ancestry patients, a pronounced association between the HLA-B*1502 genotype and Steven Johnson syndrome and/or toxic epidermal necrolysis (SJS/TEN) resulting from carbamazepine use was observed. 21 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 106 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 147 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 288 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 369 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 579 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

MeSH Pharmacological Classification Pharmacological action classes from the Medical Subject Headings (MeSH) thesaurus. https://meshb.nlm.nih.gov/record/ui?ui=D020228 225 Cytochrome P-450 CYP3A Inducers Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inducers.) 78 59 https://www.ncbi.nlm.nih.gov/sites/entrez?Db=pccompound&DbFrom=mesh&Cmd=Link&LinkName=mesh_pccompound&IdsFromResult=68065701 226 Antimanic Agents Agents that are used to treat bipolar disorders or mania associated with other affective disorders. (See all compounds classified as Antimanic Agents.) 105 44 https://www.ncbi.nlm.nih.gov/sites/entrez?Db=pccompound&DbFrom=mesh&Cmd=Link&LinkName=mesh_pccompound&IdsFromResult=68018692 227 Analgesics, Non-Narcotic A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.) 173 52 https://www.ncbi.nlm.nih.gov/sites/entrez?Db=pccompound&DbFrom=mesh&Cmd=Link&LinkName=mesh_pccompound&IdsFromResult=68018712 228 Sodium Channel Blockers A class of drugs that act by inhibition of sodium influx through cell membranes. Blockade of sodium channels slows the rate and amplitude of initial rapid depolarization, reduces cell excitability, and reduces conduction velocity. (See all compounds classified as Sodium Channel Blockers.) 236 51 https://www.ncbi.nlm.nih.gov/sites/entrez?Db=pccompound&DbFrom=mesh&Cmd=Link&LinkName=mesh_pccompound&IdsFromResult=68026941 229 Anticonvulsants Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.) 62 43 https://www.ncbi.nlm.nih.gov/sites/entrez?Db=pccompound&DbFrom=mesh&Cmd=Link&LinkName=mesh_pccompound&IdsFromResult=68000927

FDA Pharmacological Classification Pharmacologic Class is a group of active moieties that share scientifically documented properties and is defined on the basis of any combination of three attributes of the active moiety: mechanism of action (MOA), physiologic effect (PE) and chemical structure (CS). An FDA "Established Pharmacologic Class" (EPC) text phrase is a pharmacologic class associated with an approved indication of an active moiety that the FDA has determined to be scientifically valid and clinically meaningful. https://www.fda.gov/industry/structured-product-labeling-resources/pharmacologic-class ThisSection 2 Name Value 58 FDA UNII 33CM23913M 58 Active Moiety CARBAMAZEPINE 58 Pharmacological Classes Physiologic Effects [PE] - Decreased Central Nervous System Disorganized Electrical Activity 58 Pharmacological Classes Established Pharmacologic Class [EPC] - Mood Stabilizer 58 Pharmacological Classes Mechanisms of Action [MoA] - Cytochrome P450 3A4 Inducers 58 Pharmacological Classes Mechanisms of Action [MoA] - Cytochrome P450 1A2 Inducers 58 Pharmacological Classes Mechanisms of Action [MoA] - Cytochrome P450 2B6 Inducers 58 Pharmacological Classes Mechanisms of Action [MoA] - Cytochrome P450 2C9 Inducers 58 Pharmacological Classes Mechanisms of Action [MoA] - Cytochrome P450 2C19 Inducers 58 FDA Pharmacology Summary Carbamazepine is a Mood Stabilizer. The mechanism of action of carbamazepine is as a Cytochrome P450 3A4 Inducer, and Cytochrome P450 1A2 Inducer, and Cytochrome P450 2B6 Inducer, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer. The physiologic effect of carbamazepine is by means of Decreased Central Nervous System Disorganized Electrical Activity. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 63 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 273 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 144 Non-Proprietary Name CARBAMAZEPINE 144 Pharmacological Classes Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 3A4 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Mood Stabilizer [EPC]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Cytochrome P450 2C9 Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]

ATC Code The Anatomical Therapeutic Chemical (ATC) Classification System is used for the classification of drugs. This pharmaceutical coding system divides drugs into different groups according to the organ or system on which they act and/or their therapeutic and chemical characteristics. Each bottom-level ATC code stands for a pharmaceutically used substance, or a combination of substances, in a single indication (or use). This means that one drug can have more than one code: acetylsalicylic acid (aspirin), for example, has A01AD05 as a drug for local oral treatment, B01AC06 as a platelet inhibitor, and N02BA01 as an analgesic and antipyretic. On the other hand, several different brands share the same code if they have the same active substance and indications. https://www.whocc.no/atc/structure_and_principles/ 163 S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355 https://www.whocc.no/atc_ddd_index/?code=N03AF01 N03AF01 163 S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448 https://www.whocc.no/atc_ddd_index/?code=N03AF01 N03AF01 192 N - Nervous system 0 1 https://www.whocc.no/atc_ddd_index/?code=N N03 - Antiepileptics 0 3 https://www.whocc.no/atc_ddd_index/?code=N03 N03A - Antiepileptics 0 4 https://www.whocc.no/atc_ddd_index/?code=N03A N03AF - Carboxamide derivatives 0 5 https://www.whocc.no/atc_ddd_index/?code=N03AF N03AF01 - Carbamazepine 0 7 https://www.whocc.no/atc_ddd_index/?code=N03AF01

Absorption, Distribution and Excretion 30 Absorption The bioavailability of carbamazepine is in the range of 75-85% of an ingested dose. After one 200 mg oral extended-release dose of carbamazepine in a pharmacokinetic study, the Cmax carbamazepine was measured to be 1.9 ± 0.3 mcg/mL. The Tmax was 19 ± 7 hours. After several doses of 800 mg every 12 hours, the peak concentrations of carbamazepine were measured to be 11.0 ± 2.5 mcg/mL. The Tmax was reduced to 5.9 ± 1.8 hours. Extended-release carbamazepine demonstrated linear pharmacokinetics over a range of 200–800 mg. **Effect of food on absorption** A meal containing high-fat content increased the rate of absorption of one 400 mg dose but not the AUC of carbamazepine. The elimination half-life remained unchanged between fed and fasting state. The pharmacokinetics of an extended-release carbamazepine dose was demonstrated to be similar when administered in the fasted state or with food. Based on these findings, food intake is unlikely to exert significant effects on carbamazepine absorption. 23 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 131 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 182 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 333 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 444 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 665 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 800 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 983 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 30 Route of Elimination After an oral dose of radiolabeled carbamazepine, 72% of the administered radioactive dose was detected in the urine and the remainder of the ingested dose was found in the feces. Carbamazepine is mainly excreted as hydroxylated and conjugated metabolites, and minimal amounts of unchanged drug. 35 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 180 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 30 Volume of Distribution The volume of distribution of carbamazepine was found to be 1.0 L/kg in one pharmacokinetic study. Another study indicates that the volume of distribution of carbamazepine ranges between 0.7 to 1.4 L/kg.. Carbamazepine crosses the placenta, and higher concentrations of this drug are found in the liver and kidney as opposed to lung and brain tissue. Carbamazepine crosses variably through the blood-brain barrier. 30 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 158 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 205 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 351 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 30 Clearance In a pharmacokinetic study, the apparent oral clearance of carbamazepine was 25 ± 5 mL/min after one dose of carbamazepine and 80 ± 30 mL/min after several doses. 59 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 109 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Absorption: Slow and variable, but almost completely absorbed from gastrointestinal tract. 59 PEER REVIEWED PMID:8112245 Schaffler L et al; Epilepsia 35 (1): 195-8 (1994) Patients in whom carbamazepine monotherapy is discontinued for preoperative EEG/video monitoring often display toxicity if their previous maintenance dosage is resumed, even after a few days without carbamazepine. To determine whether this is due to rapid reversibility of autoinduction of carbamazepine metabolism, single-dose studies of carbamazepine pharmacokinetics were performed before and after discontinuation for monitoring in 6 adults receiving carbamazepine monotherapy. The carbamazepine-free period was 5.7 + or - 1.1 days (mean + or - SD). The pharmacokinetic parameters of carbamazepine before and after discontinuation were volume of distribution 1.28 + or - 0.29 versus 1.22 + or - 0.331/kg, elimination half-life (tl/2) 13.7 + or - 1.67 versus 22.2 + or - 2.36 hr (p < 0.001), and clearance 1.54 + or - 0.39 versus 0.92 + or - 0.32 L/kg/day (p = 0.012). Assuming that deinduction is a first-order process, a deinduction tl/2 of 3.84 days was obtained by log linear regression analysis. We showed that after carbamazepine discontinuation half of the enzymatic autoinduction is already lost after 3.84 days, indicating very rapid deinduction. Our results also provide the necessary information to predict clearance and appropriate dosage reduction for carbamazepine at time of reintroduction. 17 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 199 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 290 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 339 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 455 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 486 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 588 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:2773507 Bachmann KA et al; Xenobiotica 19 (7): 711-719 (1989) This study was designed to evaluate the usefulness of carbamazepine as a probe in screening for host factor influences on human drug metabolism. Nine healthy nonsmoking volunteers ingested a single oral dose of carbamazepine in doses ranging from 400 to 500 milligrams. Fluorescence polarization immunoassay measurements of carbamazepine concentrations in plasma and plasma ultrafiltrates from 0 to 48 hours after dosing were used to calculate clearance, volume of distribution, and clearance of plasma unbound drug. Blood samples collected 48 hours after dosing gave single sample estimates of carbamazepine clearance which were closest to multiple sample values for clearance. This was also the case for plasma total carbamazepine and plasma unbound carbamazepine. In calculating all single sample estimates of clearance, a value of 1.1 L/kg was used for V and a value of 4.3 L/kg was used to calculate the single sample estimates of clearance of plasma unbound drug. The mean prediction error was less than 5 percent errant for clearance and less than 1 percent errant for clearance of plasma unbound drug when the parameters were calculated from 48 hour concentrations of plasma total carbamazepine or plasma unbound carbamazepine, respectively. ... 54 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 211 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 324 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 595 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 719 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 752 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1189 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1221 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:11714170 Spiller HA, Carlisle RD; J Forensic Sci 46 (6): 1510-2 (2001) A fatal overdose of carbamazepine with both timely antemortem and postmortem carbamazepine concentrations /was reported/. Carbamazepine concentrations were 47.7 ug/mL 2 hr antemortem and 53 ug/mL at 9 hr postmortem. The slight rise in drug concentration may reflect continued absorption of the drug in the last 2 hr before death. Postmortem carbamazepine concentrations drawn from a peripheral vessel in this patient appeared to reflect drug concentrations at the time of death. 20 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 77 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 122 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 341 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Absorption, Distribution and Excretion (Complete) data for CARBAMAZEPINE (15 total), please visit the HSDB record page. 111 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Absorption-Distribution-and-Excretion-(Complete) 68 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Metabolism/Metabolites Metabolites are substances made or used when the body breaks down food, drugs or chemicals, or its own tissue (for example, fat or muscle tissue). This process is called metabolism and makes energy and the materials needed for growth, reproduction, and maintaining health. Metabolism also helps get rid of toxic substances. 30 Carbamazepine is largely metabolized in the liver. CYP3A4 hepatic enzyme is the major enzyme that metabolizes carbamazepine to its active metabolite, carbamazepine-10,11-epoxide, which is further metabolized to its trans-diol form by the enzyme epoxide hydrolase. Other hepatic cytochrome enzymes that contribute to the metabolism of carbamazepine are CYP2C8, CYP3A5, and CYP2B6. Carbamazepine also undergoes hepatic glucuronidation by UGT2B7 enzyme and several other metabolic reactions occur, resulting in the formation of minor hydroxy metabolites and quinone metabolites. Interestingly, carbamazepine induces its own metabolism. This leads to enhanced clearance, reduced half-life, and a reduction in serum levels of carbamazepine. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 110 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 150 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 335 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 381 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 532 7 https://pubchem.ncbi.nlm.nih.gov/compound/hydroxy PubChem Internal Link CID-961 592 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 722 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:7698101 Pisani F et al; Epilepsy Res 19 (3): 245-8 (1994) The pharmacokinetics of a single oral dose of carbamazepine-10,11-epoxide, (100 mg) were compared in 10 patients on chronic monotherapy with lamotrigine, (200-300 mg/day) and in 10 drug-free healthy control subjects. Carbamazepine-10,11-epoxide pharmacokinetic parameters in lamotridge-treated patients were found to be similar to those observed in controls (half-life: 7.2 + or - 1.6 vs 6.1 + or - 0.9 hr; apparent oral clearance: 110.8 + or - 53.1 vs 120.5 + or - 29.9 ml/h/kg; apparent volume of distribution: 1.08 + or 0.37 vs 1.04 + or - 0.25 l/kg respectively; means + or - s.d.). These data indicate that, contrary to previous suggestions, lamotridge has no effect on the metabolic disposition of carbamazepine-10,11-epoxide. 46 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 141 11 https://pubchem.ncbi.nlm.nih.gov/compound/lamotrigine PubChem Internal Link CID-3878 217 27 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 704 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 59 PEER REVIEWED PMID:7614907 Pienimaki P et al; Epilepsia 36 (3): 241-8 (1995) Placental transfer and metabolism of carbamazepine was studied in a dual recirculating placental cotyledon perfusion system and was also evaluated in 16 pairs of maternal venous and cord blood samples. ... Carbamazepine added into the maternal circulation crosses the placenta in the beginning quicker than antipyrine which is in agreement with the different lipid solubilities of these compounds. Because the transfer rates of antipyrine and carbamazepine were about the same, the mechanism of transfer of carbamazepine is probably similar to that of antipyrine (passive diffusion). No metabolites of carbamazepine could be detected in the perfusate by high-performance liquid chromatography or gas chromatography/mass spectrometry. With the improved HPLC methodology for carbamazepine metabolites, six metabolites were detected in clinical samples, including 10-hydroxy-10,11-dihydro-carbamazepine (10-OH-CBZ), which has been described earlier in only 1 uremic patient. Relative levels of metabolites showed significant individual differences. Carbamazepine crosses perfused placenta rapidly, but this does not contribute to carbamazepine metabolites detected in maternal and fetal circulation. 37 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 206 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 307 10 https://pubchem.ncbi.nlm.nih.gov/compound/antipyrine PubChem Internal Link CID-2206 428 10 https://pubchem.ncbi.nlm.nih.gov/compound/antipyrine PubChem Internal Link CID-2206 443 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 507 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 552 10 https://pubchem.ncbi.nlm.nih.gov/compound/antipyrine PubChem Internal Link CID-2206 602 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 773 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 861 38 https://pubchem.ncbi.nlm.nih.gov/compound/10-hydroxy-10%2C11-dihydrocarbamazepine PubChem Internal Link CID-114709 1046 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 1127 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:7891336 Van Belle K et al; J Pharmacol Exp Ther 272 (3): 1217-22 (1995) The aim of this work was to study the transport across the blood-brain barrier, blood and liver distribution kinetics, metabolic interaction and local liver metabolism of carbamazepine in the rat, using microdialysis with the internal standard technique as in vivo calibration method. Carbamazepine and its major metabolite, carbamazepine-10,11-epoxide, are homogeneously distributed to hippocampus and cerebellum. The ratios of the areas under the concentration-time curve for both brain regions to blood areas under the concentration-time curve were not different from unity for carbamazepine; they were 0.46 + or - 0.08 (hippocampus) and 0.45 + or - 0.05 (cerebellum) for carbamazepine-10,11-epoxide. In addition, the disposition of carbamazepine and carbamazepine-10,11-epoxide in blood and liver, after a single dose of carbamazepine, was studied in control animals and in rats after pretreatment with clomipramine. A 2-fold increase in the blood areas under concentration curve of carbamazepine and a decrease to 33% of the blood areas under concentration curve of carbamazepine-10,11-epoxide in the pretreated group demonstrate the metabolic inhibition of carbamazepine-10,11-epoxide formation by clomipramine. The ratios of the areas under concentration curve carbamazepine-10,11-epoxide to the areas under the concentration curve carbamazepine, as a measure of carbamazepine-10,11-epoxide formation, were not different for blood and liver within the control and the clomipramine-pretreated groups, but the ratios were significantly lower for liver and blood in the clomipramine group compared with the control animals. In addition, carbamazepine was administered locally in the extracellular fluid of the liver via the microdialysis probe. The liver metabolic ratio, expressed as the ratio of the formed carbamazepine-10,11-epoxide concentration to the carbamazepine concentration administered, ranged from 18.2 + or - 1.2% to 19.6 + or - 1.6%. 171 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 285 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 325 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 581 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 675 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 736 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 754 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 825 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 907 12 https://pubchem.ncbi.nlm.nih.gov/compound/clomipramine PubChem Internal Link CID-2801 987 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1071 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 1163 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 1204 12 https://pubchem.ncbi.nlm.nih.gov/compound/clomipramine PubChem Internal Link CID-2801 1268 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 1339 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1370 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 1475 12 https://pubchem.ncbi.nlm.nih.gov/compound/clomipramine PubChem Internal Link CID-2801 1574 12 https://pubchem.ncbi.nlm.nih.gov/compound/clomipramine PubChem Internal Link CID-2801 1641 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1813 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 1862 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 163 S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560 Carbamazepine has known human metabolites that include 3-Hydroxycarbamazepine, Carbamazepine 10,11-epoxide, 2-Hydroxycarbamazepine, and 9-Hydroxycarbamazepine. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 55 22 https://pubchem.ncbi.nlm.nih.gov/compound/3-Hydroxycarbamazepine PubChem Internal Link CID-135290 79 27 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine%2010%2C11-epoxide PubChem Internal Link CID-2555 108 22 https://pubchem.ncbi.nlm.nih.gov/compound/2-Hydroxycarbamazepine PubChem Internal Link CID-129274 191 Hepatic. CYP3A4 is the primary isoform responsible for the formation of carbamazepine-10,11-epoxide. This metabolite is active and shown to be equipotent to carbamazepine as an anticonvulsant. Carbamazepine is more rapidly metabolized to the aforementioned metabolite in younger patients than in adults. It also undergoes glucuronidation via UGT2B7, however this finding has been disputed. Route of Elimination: 72% of the dose is in the urine while 28% is in the feces. Hydroxylated and conjugated metabolites are largely what was recovered in the urine. 3% of the dose is recovered as unchanged carbamazepine. Half Life: Initial half-life values range from 25-65 hours, decreasing to 12-17 hours on repeated doses. 72 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 157 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 193 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 598 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Biological Half-Life The time required for a biological system (e.g., human body) to eliminate, by natural processes, half of the amount of a chemical (e.g., alcohol, medication, or radioactive material) that has entered it. 30 The mean elimination half-life of carbamazepine was 35 to 40 hours after one dose of carbamazepine extended-release formulations. The half-life ranged from 12-17 hours after several doses of carbamazepine. One pharmacokinetic study determined the elimination half-life of carbamazepine to range between 27 to 36.8 hours in healthy volunteers. 34 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 85 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 192 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 273 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Initial single dose: May range from 25 to 65 hours. Chronic dosing: May decrease to 8 to 29 hours (average 12 to 17 hours) because of autoinduciton of metabolism. 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Carbamazepine-10,11-epoxide: 5 to 8 hours. /Carbamazepine-10,11-epoxide/ 0 27 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 44 27 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555

Mechanism of Action In medicine, the term "mechanism of action" (also called MOA) is used to describe how a drug or other substance produces an effect in the body. For example, a drug's mechanism of action could be how it affects a specific target in a cell, such as an enzyme, or a cell function, such as cell growth. Knowing the mechanism of action of a drug may help provide information about the safety of the drug and how it affects the body. It may also help identify the right dose of a drug and which patients are most likely to respond to treatment. 30 Carbamazepine's mechanism of action is not fully elucidated and is widely debated. One major hypothesis is that carbamazepine inhibits sodium channel firing, treating seizure activity. Animal research studies have demonstrated that carbamazepine exerts its effects by lowering polysynaptic nerve response and inhibiting post-tetanic potentiation. In both cats and rats, carbamazepine was shown to decrease pain caused by infraorbital nerve stimulation. A decrease in the action potential in the nucleus ventralis of the thalamus in the brain and inhibition of the lingual mandibular reflex were observed in other studies after carbamazepine use. Carbamazepine causes the above effects by binding to voltage-dependent sodium channels and preventing action potentials, which normally lead to stimulatory effects on nerves. In bipolar disorder, carbamazepine is thought to increase dopamine turnover and increase GABA transmission, treating manic and depressive symptoms. A common issue that has arisen is resistance to this drug in up to 30% of epileptic patients, which may occur to altered metabolism in patients with variant genotypes. A potential therapeutic target to combat carbamazepine resistance has recently been identified as the EPHX1 gene promoter, potentially conferring resistance to carbamazepine through methylation. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 112 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 135 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 232 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 370 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 627 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 646 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 717 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 842 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 879 8 https://pubchem.ncbi.nlm.nih.gov/compound/dopamine PubChem Internal Link CID-681 910 4 https://pubchem.ncbi.nlm.nih.gov/compound/GABA PubChem Internal Link CID-119 1179 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1298 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Anticonvulsant: Exact mechanism unknown; may act postsynaptically by limiting the ability of neurons to sustain high frequency repetitive firing of action potentials through enhancement of sodium channel inactivation; in addition to altering neuronal excitability, may act presynaptically to block the release of neurotransmitter by blocking presynaptic sodium channels and the firing of action potentials, which in turn decreases synaptic transmission. 189 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 354 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Antineuralgic: Exact mechanism unknown; may involve gamma-aminobutyric acid (GABAB) receptors, which may be linked to calcium channels. 52 23 https://pubchem.ncbi.nlm.nih.gov/compound/gamma-aminobutyric%20acid PubChem Internal Link CID-119 118 7 https://pubchem.ncbi.nlm.nih.gov/element/Calcium PubChem Internal Link Element-Calcium 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Antimanic; antipsychotic: Exact mechanism is unknown; may be related to either the anticonvulsant or the antineuralgic effects of carbamazepine, or to tis effects on neurotransmitter modulator systems. 130 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703 Antidiuretic: Exact mechanism unknown; may exert a hypothalamic effect on the osmoreceptors mediated via secretion of antidiuretic hormone (ADH), or may have a direct effect on the renal tubule. 59 PEER REVIEWED For more Mechanism of Action (Complete) data for CARBAMAZEPINE (8 total), please visit the HSDB record page. 91 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Mechanism-of-Action-(Complete) 49 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Human Metabolite Information Information on metabolites generated from this compound in the human body. The data in this section is from the Human Metabolome Database. https://hmdb.ca/

Cellular Locations Cellular locations of this compound or its metabolites (e.g., cytoplasm, nucleus, lysosome, mitochondria, membrane, extracelluar). Columns 60 Cellular Locations Membrane

Metabolite Pathways Metabolic pathways related to this chemical. A metabolic pathway is a series of chemical reactions in a cell that build and breakdown molecules for cellular processes. https://bio.libretexts.org/Bookshelves/Introductory_and_General_Biology/Book%3A_General_Biology_(Boundless)/06%3A_Metabolism/6.03%3A__Energy_and_Metabolism_-_Metabolic_Pathways Columns 60 Metabolite Pathways Carbamazepine Metabolism Pathway 0 32 http://smpdb.ca/view/SMP00634 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Biochemical Reactions Biochemical reactions in which this compound participates. 199 pathwayreaction

Transformations Transformations indicate that a compound (predecessor) is transformed into another compound (successor) through a particular process (such as metabolism or fermentation) or medium (such as an animal or plant). The specificity of a transformation may vary depending on the available scientific evidence. A transformation may involve a series or cascade of changes between the predecessor (reactant) and successor (product). The presence of a successor in a sample may imply the predecessor. Predecessor: chemical being transformed. Transformation: process or medium. Successor: transformation product of predecessor. Evidence: the publication providing evidence for this transformation. Dataset: the integrated content containing the transformation information. Source: the entity or group that compiled the dataset containing the transformation information. 163 transformations

Use and Manufacturing This section provides information on the use and manufacturing information for this chemical, such as uses, consumption patterns, manufacturing methods, and U.S. imports/exports/production.

Uses Major uses of this chemical, including both consumer uses and industrial uses. 45 EPA CPDat Chemical and Product Categories The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125 cpdat 59 PEER REVIEWED Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 175 Analgesic/antiepileptic drug 59 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 288 In the treatment of pain associated with trigeminal neuralgia 59 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 288 THERAP CAT: Anticonvulsant 59 PEER REVIEWED MEDICATION 191 For the treatment of epilepsy and pain associated with true trigeminal neuralgia.

Use Classification This section contains use classification/category information for this compound from various sources. 55 Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients 56 Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients 57 Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients 163 S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664 Pharmaceuticals 163 S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448 Pharmaceuticals -> Nervous System -> Antiepileptics -> Carboxamide derivatives

Methods of Manufacturing Methods of producing this compound in an industrial scale, provided by the Hazardous Substances Data Bank (HSDB). https://pubchem.ncbi.nlm.nih.gov/source/11933 59 PEER REVIEWED SRI THERMAL DEAMMONIATION OF 2-(O-AMINOSTYRYL)ANILINE HYDROCHLORIDE TO FORM 5H-DIBENZ(B,F)AZEPINE FOLLOWED BY CONDENSATION WITH CARBAMOYL CHLORIDE IN THE PRESENCE OF SODAMIDE 72 21 https://pubchem.ncbi.nlm.nih.gov/compound/5H-DIBENZ%28B%2CF%29AZEPINE PubChem Internal Link CID-9212 124 18 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMOYL%20CHLORIDE PubChem Internal Link CID-68048 162 8 https://pubchem.ncbi.nlm.nih.gov/compound/SODAMIDE PubChem Internal Link CID-24533 59 PEER REVIEWED O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 288 Prepn: W. Schindler, US 2948718 (1960 to Geigy). 59 PEER REVIEWED Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 175 Iminostilbene + phosgene + ammonia (phosgenation/dehydrochlorination) 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Iminostilbene PubChem Internal Link CID-9212 16 8 https://pubchem.ncbi.nlm.nih.gov/compound/phosgene PubChem Internal Link CID-6371 27 7 https://pubchem.ncbi.nlm.nih.gov/compound/ammonia PubChem Internal Link CID-222 59 PEER REVIEWED Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V3 461 (2003) 5H-dibenz(b,f)azepine is first reacted with phosgene and then with ammonia. 0 21 https://pubchem.ncbi.nlm.nih.gov/compound/5H-dibenz%28b%2Cf%29azepine PubChem Internal Link CID-9212 44 8 https://pubchem.ncbi.nlm.nih.gov/compound/phosgene PubChem Internal Link CID-6371 67 7 https://pubchem.ncbi.nlm.nih.gov/compound/ammonia PubChem Internal Link CID-222

Formulations/Preparations Information on Formulations/Preparations of this chemical, collected by the Hazardous Substances Data Bank (HSDB) from various sources. https://pubchem.ncbi.nlm.nih.gov/source/11933 59 PEER REVIEWED McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2225 Oral: Capsules, extended-release: 200 mg Carbatrol (with povidone), (Shire US); 300 mg Carbatrol (with povidone), (Shire US). Suspension: 100 mg/5 mL Carbamazepine Suspension, (Actavis), Carbamazepine Suspension, (Morton Grove), Carbamazepine Suspension, (Taro); Tegretol ( with propylene glycol), (Novartis). Tablets: 200 mg Epitol (scored), (Teva), Tegretol (scored), (Novartis). Tablets, chewable: 100 mg Tegretol (scored), (Novartis). Tablets, extended-release: 100 mg Tegretol-XR (with mannitol), (Novartis); 200 mg Tegretol-XR (with mannitol), (Novartis); 400 mg Tegretol-XR (with mannitol), (Novartis). 41 9 https://pubchem.ncbi.nlm.nih.gov/compound/Carbatrol PubChem Internal Link CID-2554 57 8 https://pubchem.ncbi.nlm.nih.gov/compound/povidone PubChem Internal Link CID-6917 87 9 https://pubchem.ncbi.nlm.nih.gov/compound/Carbatrol PubChem Internal Link CID-2554 103 8 https://pubchem.ncbi.nlm.nih.gov/compound/povidone PubChem Internal Link CID-6917 150 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 187 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 229 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 263 8 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol PubChem Internal Link CID-2554 279 16 https://pubchem.ncbi.nlm.nih.gov/compound/propylene%20glycol PubChem Internal Link CID-1030 326 6 https://pubchem.ncbi.nlm.nih.gov/compound/Epitol PubChem Internal Link CID-2554 351 8 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol PubChem Internal Link CID-2554 408 8 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol PubChem Internal Link CID-2554 473 11 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol-XR PubChem Internal Link CID-2554 491 8 https://pubchem.ncbi.nlm.nih.gov/compound/mannitol PubChem Internal Link CID-6251 521 11 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol-XR PubChem Internal Link CID-2554 539 8 https://pubchem.ncbi.nlm.nih.gov/compound/mannitol PubChem Internal Link CID-6251 569 11 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol-XR PubChem Internal Link CID-2554 587 8 https://pubchem.ncbi.nlm.nih.gov/compound/mannitol PubChem Internal Link CID-6251

Consumption Patterns Consumption patterns of this chemical and products containing it, collected by the Hazardous Substances Data Bank (HSDB) from various sources. 59 PEER REVIEWED PMID:12448549 Jones OAH et al; Water Res 36: 5013-22 (2002) Amount used per year in the UK: 40.348.75 kg 59 PEER REVIEWED Pfluger P, Dietrich DR; pp 11-17 in Amer Chem Soc, ACS Symp Ser, 791(Pharmaceuticals and personal care products in the environment): 11-17 (2001) (1995) estimated prescription amount in Germany was calculated to be 80 tons

U.S. Production The amount of this chemical produced/manufactured in the U.S. 59 PEER REVIEWED SRI (1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS 59 PEER REVIEWED SRI (1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Identification This section contains laboratory methods used to identify this chemical.

Analytic Laboratory Methods Analytic laboratory methods for analyzing this compound in a sample. The information in this section is collected by the Hazardous Substances Data Bank (HSDB) from various sources. 59 PEER REVIEWED U.S. Pharmacopeia. The United States Pharmacopeia, USP 30/The National Formulary, NF 25; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1615 (2007) Analyte: carbamazepine; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED U.S. Pharmacopeia. The United States Pharmacopeia, USP 30/The National Formulary, NF 25; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1615 (2007) Analyte: carbamazepine; matrix: chemical purity; procedure: liquid chromatography with detection at 230 nm and comparison to standards 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED U.S. Pharmacopeia. The United States Pharmacopeia, USP 30/The National Formulary, NF 25; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1616 (2007) Analyte: carbamazepine; matrix: pharmaceutical preparation (oral suspension; tablet); procedure: infrared absorption spectrophotometry with comparison to standards (chemical identification) 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED U.S. Pharmacopeia. The United States Pharmacopeia, USP 30/The National Formulary, NF 25; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1616 (2007) Analyte: carbamazepine; matrix: pharmaceutical preparation (oral suspension; tablet); procedure: liquid chromatography with detection at 230 nm and comparison to standards (chemical purity) 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Analytic Laboratory Methods (Complete) data for CARBAMAZEPINE (8 total), please visit the HSDB record page. 99 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Analytic-Laboratory-Methods-(Complete) 57 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Clinical Laboratory Methods Clinical laboratory methods for detecting, isolating, separating, and/or analyzing this compound in a sample. The information in this section is collected by the Hazardous Substances Data Bank (HSDB) from various sources. 59 PEER REVIEWED Capparella M et al; J Chromatogr A, 691: 141-150 (1995). As cited in: Lunn G, Schmuff N; HPLC Methods for Pharmaceutical Analysis. New York, NY: John Wiley & Sons, 1997, p.224 Analyte: carbamazepine; matrix: blood (serum); procedure: high-performance liquid chromatography with ultraviolet detection at 214 nm 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Lanchote VL et al; Ther Drug Monit, 27: 47-52 (1995). As cited in: Lunn G, Schmuff N; HPLC Methods for Pharmaceutical Analysis. New York, NY: John Wiley & Sons, 1997, p.224 Analyte: carbamazepine; matrix: blood (plasma); procedure: high-performance liquid chromatography with ultraviolet detection at 220 nm 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Nimura N et al; J Chromatogr A, 689: 203-210 (1995). As cited in: Lunn G, Schmuff N; HPLC Methods for Pharmaceutical Analysis. New York, NY: John Wiley & Sons, 1997, p.225 Analyte: carbamazepine; matrix: blood (serum); procedure: high-performance liquid chromatography with ultraviolet detection at 254 nm 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Pienimaki P et al; J Chromatogr B, 673: 97-105 (1995). As cited in: Lunn G, Schmuff N; HPLC Methods for Pharmaceutical Analysis. New York, NY: John Wiley & Sons, 1997, p.226 Analyte: carbamazepine; matrix: blood (serum); procedure: high-performance liquid chromatography with ultraviolet detection at 212 nm; limit of detection: 10 ng/mL 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Clinical Laboratory Methods (Complete) data for CARBAMAZEPINE (17 total), please visit the HSDB record page. 100 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Clinical-Laboratory-Methods-(Complete) 57 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Safety and Hazards Information on safety and hazards for this compound, including safety/hazards properties, reactivity, incompatibilities, management techniques, first aid treatments, and more. For toxicity and related information, please see the Toxicity section.

Hazards Identification This section identifies the hazards of the chemical presented on the safety data sheet (SDS) and the appropriate warning information associated with those hazards. The information in this section includes, but are not limited to, the hazard classification of the chemical, signal word, pictograms, hazard statements and precautionary statements. https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

GHS Classification GHS (Globally Harmonized System of Classification and Labelling of Chemicals) is a United Nations system to identify hazardous chemicals and to inform users about these hazards. GHS has been adopted by many countries around the world and is now also used as the basis for international and national transport regulations for dangerous goods. The GHS hazard statements, class categories, pictograms, signal words, and the precautionary statements can be found on the PubChem GHS page. https://pubchem.ncbi.nlm.nih.gov/ghs/ ThisSection 2 Name Value 1 48 Pictogram(s) 0 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS07.svg Icon Irritant 1 1 https://pubchem.ncbi.nlm.nih.gov/images/ghs/GHS08.svg Icon Health Hazard 48 Signal Danger 0 6 Color GHSDanger 48 GHS Hazard Statements H302 (96.63%): Harmful if swallowed [Warning Acute toxicity, oral] 37 7 Color GHSWarning H317 (94.71%): May cause an allergic skin reaction [Warning Sensitization, Skin] 52 7 Color GHSWarning H334 (87.98%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory] 90 6 Color GHSDanger 48 Precautionary Statement Codes P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) 64 18 https://pubchem.ncbi.nlm.nih.gov/ghs/#_prec 48 ECHA C&L Notifications Summary Aggregated GHS information provided by 209 companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. 0 166 Italics Reported as not meeting GHS hazard criteria by 1 of 209 companies. For more detailed information, please visit ECHA C&L website. 0 133 Italics 112 20 https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/27286 Of the 23 notification(s) provided by 208 of 209 companies with hazard statement code(s). 0 89 Italics Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. 0 281 Italics

Hazard Classes and Categories The Hazard Classes and Categories are aligned with GHS (Globally Harmonized System of Classification and Labelling of Chemicals) hazard statement codes. The percentage data in the parenthesis from ECHA indicates that the hazard classes and categories information are consolidated from multiple companies. Also, see the detailed explanation from the above GHS classification section. https://pubchem.ncbi.nlm.nih.gov/ghs/ 2 48 Acute Tox. 4 (96.63%) Skin Sens. 1 (94.71%) Resp. Sens. 1 (87.98%)

Accidental Release Measures This section provides recommendations on the appropriate response to spills, leaks, or releases, including containment and cleanup practices to prevent or minimize exposure to people, properties, or the environment. It may also include recommendations distinguishing between responses for large and small spills where the spill volume has a significant impact on the hazard. https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

Disposal Methods Disposal methods or procedures for this chemical or hazardous waste containing it. 59 PEER REVIEWED SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Handling and Storage This section provides guidance on the safe handling practices and storage conditions for this chemical. The information in this section includes precautions for safe handling, such as recommendations for handling incompatible chemicals, minimizing the release of the chemical into the environment, and providing advice on general hygiene practices (e.g., eating, drinking, and smoking in work areas is prohibited). In addition, this section provides recommendations on the conditions for safe storage (including any incompatibilities) as well as advice on specific storage requirements (e.g., ventilation requirements). https://www.osha.gov/sites/default/files/publications/OSHA3514.pdf

Storage Conditions Conditions for safe storage of this compound, including any incompatible chemicals and specific storage requirements (e.g., ventilation requirements). 59 PEER REVIEWED McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2225 Carbamazepine tablets, extended-release tablets, and chewable tablets should be stored in tight, light-resistant containers at temperatures not exceeding 30 °C. Carbamazepine extended-release capsules should be stored in tight, light-resistant containers at 15-25 °C. Because dissolution characteristics and associated oral bioavailability of carbamazepine tablets may be affected substantially by moisture, patients should be cautioned to keep containers of the tablets tightly closed and in a dry location, away from areas with excessive moisture (e.g., showers, bathrooms, humidifiers). Carbamazepine tablets may lose one-third or more of their oral bioavailability when exposed to excessive moisture. Tablets continuously exposed to 97% relative humidity at room temperature for 2 weeks become hardened and dissolve poorly. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 161 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 343 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 590 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Regulatory Information This section lists the regulations related to the safety, health, and environment of the chemical and its associated products. The regulatory information, which may encompass national and/or regional regulations pertaining to the chemical or mixtures, is presented solely for informational purposes. For additional details, please consult the links to the information sources provided under each data entry. 147 New Zealand EPA Inventory of Chemical Status Carbamazepine: Does not have an individual approval but may be used under an appropriate group standard 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

FDA Requirements FDA requirements regarding this chemical and products containing it. FDA Requirements means any requirements of the Federal Food, Drug and Cosmetic Act (FDCA), as amended, and any rules or regulations promulgated thereunder which are or may be applicable to the manufacture, sale, labeling or distribution of the products regulated by FDA (e.g., drugs, biologics, dietary supplements, foods, cosmetics, tobacco products, etc.). https://www.fda.gov/regulatory-information/laws-enforced-fda/federal-food-drug-and-cosmetic-act-fdc-act 59 PEER REVIEWED 21 CFR 200-299, 300-499, 820, and 860 (4/1/93) Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392). 59 PEER REVIEWED DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of July 24, 2007: https://www.fda.gov/cder/ob/ The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl carbamazepine approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. 137 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Toxicity Toxicity information related to this compound, including routes of exposure, related symptoms, acute and chronic effects, and numerical measures of toxicity.

Toxicological Information This section provides toxicological and health effects information for the chemical. It includes the likely routes of exposure (inhalation, ingestion, skin and eye contact), and the delayed, immediate, or chronic effects/symptoms from short- and long-term exposure, and the numerical measures of toxicity [e.g., acute toxicity estimates such as the LD50 (median lethal dose, the estimated amount of a chemical expected to kill 50% of test animals in a single dose)]. This section also includes information on whether the chemical is considered as a potential carcinogen according to authoritative sources such as the National Toxicology Program (NTP) Report on Carcinogens and the International agency for Research on Cancer (IARC) Monographs.

Toxicity Summary Summary of the toxicity of this compound, provided by the Hazardous Substances Data Bank (HSDB) and other sources. 191 Carbamazepine inhibits sustained repetitive firing by blocking use-dependent sodium channels. Pain relief is believed to be associated with blockade of synaptic transmission in the trigeminal nucleus and seizure control with reduction of post-tetanic potentiation of synaptic transmission in the spinal cord. Carbamazepine also possesses anticholinergic, central antidiuretic, antiarrhythmic, muscle relaxant, antidepressant (possibly through blockade of norepinephrine release), sedative, and neuromuscular-blocking properties. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 77 6 https://pubchem.ncbi.nlm.nih.gov/element/Sodium PubChem Internal Link Element-Sodium 309 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 455 14 https://pubchem.ncbi.nlm.nih.gov/compound/norepinephrine PubChem Internal Link CID-439260

Hepatotoxicity This section provides a short description about the hepatotoxicity associated with this compound, the rate of serum enzyme elevations during use, and the frequency and character of the clinically apparent liver injury associated with the compound. 73 Prospective studies indicate that a sizeable proportion of patients taking carbamazepine have transient serum aminotransferase elevations (ranging from 1% to 22%). These elevations are usually benign, not associated with liver histological abnormalities and usually resolve even with drug continuation. In addition, most patients on carbamazepine develop mild-to-moderate elevations in gamma glutamyltranspeptidase (GGT) levels, probably indicative of hepatic enzyme induction rather than liver injury. Marked aminotransferase elevations (more than 5 fold elevated) occur less frequently. 75 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 333 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Clinically apparent hepatotoxicity from carbamazepine is uncommon but well described, there being several hundred cases reported in the literature. Carbamazepine hepatotoxicity most often occurs in the setting of anticonvulsant hypersensitivity syndrome with onset of fever, followed by rash, facial edema, lymphadenopathy, elevations in white count and eosinophilia or atypical lymphocytosis, 1 to 8 weeks after starting therapy (Case 1 and 2). This syndrome is usually referred to as Drug Rash with Eosinophilia and Systemic Symptoms [DRESS]. The most frequent form of systemic involvement in DRESS syndrome is liver injury. The liver involvement ranges from mild and transient elevations in serum enzymes to abrupt onset of an acute hepatitis-like syndrome that can be severe and even fatal. However, the most common pattern of enzyme elevations in carbamazepine related DRESS syndrome is a mixed or cholestatic injury. Liver biopsy shows the cholestatic injury with focal hepatocellular necrosis, prominence of eosinophils and occasionally granulomas. In fatal cases, liver histology also shows bridging, submassive or massive necrosis. Other systemic involvement in carbamazepine induced DRESS syndrome includes myositis, nephritis and pneumonitis. Carbamazepine induced DRESS syndrome has also been linked to several cases of vanishing bile duct syndrome in which a severe cholestatic hepatitis with immunoallergic features is followed by persistence of cholestasis with itching, jaundice and prominent elevations in alkaline phosphatase levels. In most instances, vanishing bile duct syndrome gradually improves with time, but some instances are severe and unremitting, leading eventually to end stage liver disease and death or need for liver transplantation several months or even years fter onset (Case 3). 40 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 148 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 852 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1171 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1254 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 Carbamazepine hepatotoxicity can also occur without immunoallergic features in which case the latency to onset can be as long as 6 to 12 months after starting. The cases of carbamazepine liver injury without immunoallergic features tend to be hepatocellular rather than cholestatic or mixed and are more likely to be severe (Case 4). Carbamazepine is a commonly listed agent in case series of acute liver failure. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 173 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 334 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 Likelihood score: A (Well established cause of clinically apparent liver injury).

Drug Induced Liver Injury This compound's potential to cause drug-induced liver injury. This information is from the FDA's Drug-Induced Liver Injury Rank (DILIrank) dataset. DILIrank groups more than 1,000 FDA-approved drugs into 4 categories (most-, less-, no-, and ambiguous-DILI-concerns). DILIrank assigns a severity grade, ranging from 0 (no-DILI-concern) to 8 (fatal hepatotoxicity). https://www.fda.gov/science-research/liver-toxicity-knowledge-base-ltkb/drug-induced-liver-injury-rank-dilirank-dataset ThisSection 2 Name Value 29 Compound carbamazepine 29 DILI Annotation Most-DILI-Concern 29 Severity Grade 7 29 Label Section Warnings and precautions 29 References M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007 165 13 https://pubmed.ncbi.nlm.nih.gov/21624500/ 179 32 https://doi.org/10.1016/j.drudis.2011.05.007 M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015 202 13 https://pubmed.ncbi.nlm.nih.gov/26948801/ 216 32 https://doi.org/10.1016/j.drudis.2016.02.015

Carcinogen Classification This section provides the International Agency for Research on Cancer (IARC) Carcinogenic Classification and related monograph links. In the IARC Carcinogenic classification, chemicals are categorized into four groups: Group 1 (carcinogenic to humans), Group 2A (probably carcinogenic to humans), Group 2B (possibly carcinogenic to humans), and Group 3 (not classifiable as to its carcinogenicity to humans). https://monographs.iarc.who.int/agents-classified-by-the-iarc/ ThisSection 2 Name Value 191 No indication of carcinogenicity to humans (not listed by IARC).

Health Effects Principal effect(s) of exposure to each substance, listed by OSHA Health Code, Health Effects from various sources. 191 May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Effects During Pregnancy and Lactation Drug effects during pregnancy and lactation. 31 ◉ Summary of Use during Lactation Breastfeeding during carbamazepine monotherapy does not appear to adversely affect infant growth or development, and breastfed infants had higher IQs and enhanced verbal abilities than nonbreastfed infants at 6 years of age in one study. A safety scoring system finds carbamazepine possible to use during breastfeeding. If carbamazepine is required by the mother, it is not a reason to discontinue breastfeeding. 21 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 268 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 323 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Carbamazepine and its active metabolite have relatively high levels in breastmilk and breastfed infants have serum levels that are sometimes measurable, but usually well below the anticonvulsant therapeutic range. Most infants have had no adverse reactions, but sedation, poor sucking, withdrawal reactions and 3 cases of hepatic dysfunction have been reported. These have all been complicated because of intrauterine exposure and, in some cases, concurrent drug therapy. Monitor the infant for jaundice, drowsiness, adequate weight gain, and developmental milestones, especially in younger, exclusively breastfed infants and when using combinations of anticonvulsant or psychotropic drugs. One author recommends monitoring infant serum carbamazepine levels, liver enzymes, and a complete blood count during therapy. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 737 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◉ Effects in Breastfed Infants No adverse effects were noted by the mothers in 3 breastfed infants during maternal carbamazepine and phenytoin therapy. 84 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 102 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 An epileptic woman taking carbamazepine 1 gram and primidone 1 gram daily during pregnancy and postpartum breastfed her infant for 5 weeks and noted no difference in activity in the infant before and after nursing. 26 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 51 9 https://pubchem.ncbi.nlm.nih.gov/compound/primidone PubChem Internal Link CID-4909 A probable case of drug-induced drowsiness occurred in a newborn whose mother was taking primidone, carbamazepine and phenytoin (dosages not stated). At day 30, breastfeeding was discontinued because of the drowsiness that occurred after each feeding and poor weight gain. The same group of researchers found that 15 partially breastfed infants whose mothers were taking various anticonvulsants, including carbamazepine, gained weight at a slower rate during the first 5 days postpartum than did 75 infants of epileptic mothers who bottle fed or control mothers taking no medications. 89 9 https://pubchem.ncbi.nlm.nih.gov/compound/primidone PubChem Internal Link CID-4909 100 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 118 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 406 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 A 10-week-old breastfed infant whose mother was taking clemastine, phenytoin and carbamazepine was drowsy, refused to feed, was irritable, and had high-pitched crying. These side effects were possibly caused by clemastine in breastmilk, but carbamazepine could also have contributed. 55 10 https://pubchem.ncbi.nlm.nih.gov/compound/clemastine PubChem Internal Link CID-26987 67 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 81 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 211 10 https://pubchem.ncbi.nlm.nih.gov/compound/clemastine PubChem Internal Link CID-26987 241 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Poor sucking, vomiting and lack of weight gain was reported in a partially breastfed 4-week-old whose mother was taking carbamazepine monotherapy in a dose of 11 mg/kg daily. 120 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Weak sucking occurred in 1 of 15 breastfed infants whose mothers were on carbamazepine monotherapy, but a causal relationship could not be confirmed. 73 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 A breastfed infant whose mother was taking primidone 375 mg, phenobarbital 90 mg, and carbamazepine 800 mg daily did well despite a saliva phenobarbital level of 3.4 mg/L. At 7 months of age, after the mother abruptly stop nursing, the infant had a number of "startle reactions" and infantile seizures occurred which were confirmed by an abnormal electroencephalogram. Continued phenobarbital administration to the infant for 15 months controlled the seizures and no more occurred up to 5 years of age. 43 9 https://pubchem.ncbi.nlm.nih.gov/compound/primidone PubChem Internal Link CID-4909 61 13 https://pubchem.ncbi.nlm.nih.gov/compound/phenobarbital PubChem Internal Link CID-4763 86 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 139 13 https://pubchem.ncbi.nlm.nih.gov/compound/phenobarbital PubChem Internal Link CID-4763 379 13 https://pubchem.ncbi.nlm.nih.gov/compound/phenobarbital PubChem Internal Link CID-4763 A 3-week-old infant whose mother was taking carbamazepine monotherapy 600 mg daily during pregnancy and postpartum had persistent jaundice from birth. Cholestasis and elevated hepatic transaminases were found. Jaundice slowly resolved after discontinuation of breastfeeding on day 17 of life, but transaminase values increased to a peak 6.5 weeks after discontinuation of breastfeeding. Cholestatic hepatitis was possibly caused by carbamazepine exposure in utero and in breastmilk. 44 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 432 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 An infant was born to a mother who was taking carbamazepine monotherapy 400 mg daily during pregnancy and postpartum. The infant was exclusively breastfed for 9 days, then partially breastfed. Jaundice was present at birth and serum gamma-glutamyltransferase (GGT) levels were elevated and remained elevated for at least 25 days, even after bilirubin levels decreased. The infant had a rare form of ABO incompatibility, but this was not thought to fully explain the elevated GGT levels. At 2, 4 and 6 months of age, the infant was developing normally. Serum carbamazepine levels were 1.8 and 1.1 mg/L at 2 days and 63 days of age. The transient hepatic dysfunction was possibly caused by carbamazepine exposure in utero and in breastmilk. 46 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 341 9 https://pubchem.ncbi.nlm.nih.gov/compound/bilirubin PubChem Internal Link CID-5280352 558 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 688 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 In a telephone follow-up study, mothers reported no side effects among 6 infants exposed to carbamazepine (ages and dosages not stated) in breastmilk. 92 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 One author reported a mother who was taking clonazepam 6 mg daily and carbamazepine 1400 mg daily. The infant had serum clonazepam levels of about 40% of the mother's serum level. Her infant was described as "somewhat lazy at the breast and tired." Carbamazepine levels were not reported. 44 10 https://pubchem.ncbi.nlm.nih.gov/compound/clonazepam PubChem Internal Link CID-2802 70 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 120 10 https://pubchem.ncbi.nlm.nih.gov/compound/clonazepam PubChem Internal Link CID-2802 249 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 Possible drug-induced seizure-like activity and cyanosis occurred in a breastfed 3-week-old whose mother was taking fluoxetine, carbamazepine and buspirone during pregnancy and postpartum. 116 10 https://pubchem.ncbi.nlm.nih.gov/compound/fluoxetine PubChem Internal Link CID-3386 128 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 146 9 https://pubchem.ncbi.nlm.nih.gov/compound/buspirone PubChem Internal Link CID-2477 A breastfed 3-month-old whose mother was taking carbamazepine 200 mg in the morning and 300 mg at bedtime had normal liver function tests. 48 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 A fullterm infant whose mother was taking carbamazepine 400 mg daily during pregnancy and postpartum developed asphyxia at birth and required mechanical ventilation. Transient jaundice and liver enzyme elevation were attributed to asphyxia. The mother began breastfeeding on day 8 postpartum. At 3 to 7 weeks of age, cholestasis, jaundice and elevation of hepatic transaminases occurred. The late hepatic abnormalities were considered to be probably caused by carbamazepine in breastmilk. 42 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 460 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Two infants were breastfed during maternal therapy with carbamazepine 600 and 1200 mg daily and levetiracetam. The infants appeared to remain healthy throughout the 6- to 8-week study period. 56 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 96 13 https://pubchem.ncbi.nlm.nih.gov/compound/levetiracetam PubChem Internal Link CID-5284583 In a long-term study on infants exposed to anticonvulsants during breastfeeding, no difference in average intelligence quotient at 3 years of age was found between infants who were breastfed (n = 26) a median of 6 months and those not breastfed (n = 32) when their mothers were taking carbamazepine. Breastfeeding during carbamazepine monotherapy does not appear to adversely affect infant growth or development, and breastfed infants had slightly higher IQs and enhanced verbal abilities than nonbreastfed infants at 6 years of age in one study. Combination therapy with sedating anticonvulsants or psychotropics may result in infant sedation or withdrawal reactions. 285 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 321 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 A prospective cohort study in Norway followed infants of mothers who took antiepileptic drugs during pregnancy and lactation and compared them to infants of mothers with untreated epilepsy and infants with fathers who took antiepileptics as control groups. Of the 223 mothers studied, 48 were taking carbamazepine monotherapy. Infants were assessed at 6, 18 and 36 months of age. Continuous breastfeeding in children of women using antiepileptic drugs was associated with no greater impaired development than those with no breastfeeding or breastfeeding for less than 6 months. 300 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 An exclusively breastfed infant, whose mother took carbamazepine 1200 mg daily during late pregnancy and postpartum, had poor weight gain, poor sucking, and vomiting beginning at birth with normal neurological and laboratory tests. Because gastroesophageal reflux was suspected, ranitidine and food thickeners were tried, but were unsuccessful. High milk and plasma carbamazepine levels were found. Partial formula feeding did not resolve the problem, but cessation of breastfeeding resolved the symptoms rapidly. The adverse effect was probably caused by carbamazepine. 51 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 279 10 https://pubchem.ncbi.nlm.nih.gov/compound/ranitidine PubChem Internal Link CID-5039 366 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 556 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. One woman on long-term carbamazepine therapy had slight galactorrhea 3.5 years after delivery, although her serum prolactin was normal. The prolactin level in a mother with established lactation may not affect her ability to breastfeed. 93 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 140 ◈ What is carbamazepine? Carbamazepine is a medication used to control seizures. It is also used to treat other conditions, such as bipolar disorder, schizophrenia, or pain disorders. A common brand name for carbamazepine is Tegretol®, but there are others. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 183 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 200 8 https://pubchem.ncbi.nlm.nih.gov/compound/Tegretol PubChem Internal Link CID-2554 ◈ I take carbamazepine. Can it make it harder for me to become pregnant? 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Women with seizure disorders who use seizure medications for a long time might have irregular periods and difficulty becoming pregnant. Talk to your healthcare provider if you are having trouble getting pregnant. ◈ I just found out that I am pregnant. Should I stop taking carbamazepine? 60 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Pregnant women should not stop this medication without talking to a healthcare provider. Having a seizure while pregnant may be harmful to the baby. Women with bipolar disorder who stop taking medication during their pregnancy may be at an increased risk for episodes of depression or mania that could be harmful to both the mother and the baby.If possible, women with seizure disorders or bipolar disorder who could become pregnant should discuss their options for treatment, including medications, with their healthcare providers before becoming pregnant. ◈ Does taking carbamazepine increase the chance for miscarriage? 14 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Miscarriage can occur in any pregnancy. A few studies have seen slightly more miscarriages among those taking carbamazepine during pregnancy. Other studies have not seen this. Having a health condition that requires carbamazepine might be a reason for the small increase of miscarriage in the studies. 110 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 216 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◈ Does taking carbamazepine increase the chance of birth defects? 14 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 In every pregnancy, a woman starts out with a 3-5% chance of having a baby with a birth defect. This is called her background risk. Studies looking at women who have taken carbamazepine during the first trimester of pregnancy have found an increased chance of neural tube defects (when the spinal cord or skull do not form properly). The most common neural tube defect is spina bifida. The chance for neural tube defects in the general population is less than 1% (less than 1 in 100). Taking carbamazepine might increase that chance to about 1%.Folic acid has been found to reduce the background risk for neural tube defects. If you take carbamazepine, your healthcare provider might recommend that you take extra folic acid before and during pregnancy.Other studies have reported a greater chance for other major birth defects, such as heart defects or cleft lip. Some studies have also suggested an increased chance for minor birth defects such as a small nose with a long space between the nose and upper lip, and small finger and toenails. Other studies have reported an increased chance of growth issues and small head size.The chance for birth defects might increase with higher doses of carbamazepine, especially in early pregnancy. Talk to your healthcare provider about the lowest effective dose for your condition, and about the risks and benefits of your treatment. Blood tests and ultrasounds can screen for neural tube defects and other birth defects. 172 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 492 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 545 10 https://pubchem.ncbi.nlm.nih.gov/compound/Folic%20acid PubChem Internal Link CID-135398658 638 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 714 10 https://pubchem.ncbi.nlm.nih.gov/compound/folic%20acid PubChem Internal Link CID-135398658 1194 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◈ Could taking carbamazepine in the second or third trimester cause other pregnancy complications? 15 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 In rare cases, taking carbamazepine during pregnancy can cause bleeding problems in the newborn due to low vitamin K levels. Women taking carbamazepine in pregnancy should ask their healthcare providers about taking vitamin K supplements near the end of their pregnancies. They can also talk to their child’s pediatrician before delivery about giving the newborn a vitamin K supplement at birth. 22 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 138 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◈ Does taking carbamazepine in pregnancy cause long-term problems in behavior or learning for the baby? 14 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Researchers are just beginning to look at the development of children who have been exposed to carbamazepine during pregnancy. Some studies have found a small increased chance for developmental delays. Other studies have found no differences in development or IQ. More studies are needed to know the long-term effects of carbamazepine. 95 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 321 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◈ Can I breastfeed while taking carbamazepine? 32 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Carbamazepine passes into breast milk. However, the amount the baby might swallow in the milk is not expected to affect the infant. Breastfeeding while taking carbamazepine by itself (no additional seizure medications) does not appear to affect infant growth or development. Some healthcare providers can measure levels of carbamazepine in the baby’s system if there is concern. Be sure to talk to your healthcare provider about all your breastfeeding questions. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 159 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 323 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 ◈ If a man takes carbamazepine, could it affect his fertility (ability to get his partner pregnant) or increase the chance of birth defects? 17 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 One small animal study and a couple small human studies have suggested that carbamazepine might affect sperm development, but the studies did not look at whether or not this caused problems with starting a pregnancy. More studies are needed to know if men who take carbamazepine have a harder time getting their partners pregnant. In general, exposures that fathers have are unlikely to increase risks to a pregnancy. For more information, please see the MotherToBaby fact sheet Paternal Exposures and Pregnancy at https://mothertobaby.org/fact-sheets/paternal-exposures-pregnancy/pdf/. 76 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 265 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Exposure Routes The way people or other living organisms may come into contact with a hazardous chemical. Examples of common exposure routes are inhalation, ingestion, skin/eye contact. 191 Oral. In clinical studies, carbamazepine suspension, conventional tablets, and extended-release tablets delivered equivalent amounts of drug to the systemic circulation. However, it has been observed that the suspension is somewhat faster absorbed. Furthermore, the extended-release tablet is slightly slower than the conventional tablet. The bioavailability of the extended-release tablet is 89%, compared to the suspension. Plasma levels of carbamazepine are variable. The time to peak concentration for the different formulations are as follows: Suspension = 1.5 hours; Conventional tablets = 4-5 hours; Extended-release tablets = 3-12 hours. 27 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 443 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Symptoms Symptoms of exposure to this chemical through various routes (for example, ingestion, inhalation, skin contact, and eye contact). 191 Mild ingestions cause vomiting, drowsiness, ataxia, slurred speech, nystagmus, dystonic reactions, and hallucinations. Severe intoxications may produce coma, seizures, respiratory depression, and hypotension

Acute Effects The results from acute animal tests and/or acute human studies are presented in this section. Acute animal studies consist of LD50 and LC50 tests, which present the median lethal dose (or concentration) to the animals. Acute human studies usually consist of case reports from accidental poisonings or industrial accidents. These case reports often help to define the levels at which acute toxic effects are seen in humans. 10 chemidplus

Treatment Treatment when exposed to toxin 191 The prognosis in cases of severe poisoning is critically dependent upon prompt elimination of the drug, which may be achieved by inducing vomiting, irrigating the stomach, and by taking appropriate steps to diminish absorption. If these measures cannot be implemented without risk on the spot, the patient should be transferred at once to a hospital, while ensuring that vital functions are safeguarded. There is no specific antidote. (L1712)

Interactions Interactions of this compound with other chemicals, according to the Hazardous Substances Data Bank (HSDB). https://pubchem.ncbi.nlm.nih.gov/source/11933 59 PEER REVIEWED PMID:8573214 Gennings C et al; Arzneimittelforschung 45 (7): 739-48 (1995) Various combinations of carbamazepine, felbamate, and phenytoin were evaluated in mice (ip) for anticonvulsant activity (maximal electroshock seizure test) and minimal neurotoxicity (rotarod test). The results obtained from these studies were analyzed using response surface methodologies. The outcomes of these analyses in regard to anticonvulsant activity suggest that, under these experimental study conditions, at 0.5 hr post treatment there is a significant carbamazepine/phenytoin synergism even though none of the drugs has a significant dose-response by that time when given alone, and that at l.0 hr post treatment, the combination dose-response is additive. Thus, there appears to be an important dose/time relationship. In regard to the neurotoxic response, the results suggest a significant carbamazepine/phenytoin synergism at 0.25 hr post treatment and an additive neurotoxic effect due to the combination of felbamate/carbamazepine/phenytoin at 0.5, l.0 and 2.0 hr post exposure. 24 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 39 9 https://pubchem.ncbi.nlm.nih.gov/compound/felbamate PubChem Internal Link CID-3331 54 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 463 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 477 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 803 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 817 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 923 9 https://pubchem.ncbi.nlm.nih.gov/compound/felbamate PubChem Internal Link CID-3331 933 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 947 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 704 Risk of hepatotoxicity with single toxic doses or prolonged use of high doses of acetaminophen may be increased, and therapeutic effects of acetaminophen may be decreased, in patients taking hepatic enzyme-inducing agents such as carbamazepine. 81 13 https://pubchem.ncbi.nlm.nih.gov/compound/acetaminophen PubChem Internal Link CID-1983 140 13 https://pubchem.ncbi.nlm.nih.gov/compound/acetaminophen PubChem Internal Link CID-1983 230 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 704 Concurrent use /of aminophylline, oxtriphylline, or theophylline/ with carbamazepine may stimulate hepatic metabolism of the xanthines (except dyphylline), resulting in increased theophylline clearance. 19 13 https://pubchem.ncbi.nlm.nih.gov/compound/aminophylline PubChem Internal Link CID-9433 34 13 https://pubchem.ncbi.nlm.nih.gov/compound/oxtriphylline PubChem Internal Link CID-656652 52 12 https://pubchem.ncbi.nlm.nih.gov/compound/theophylline PubChem Internal Link CID-2153 71 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 143 10 https://pubchem.ncbi.nlm.nih.gov/compound/dyphylline PubChem Internal Link CID-3182 179 12 https://pubchem.ncbi.nlm.nih.gov/compound/theophylline PubChem Internal Link CID-2153 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 705 Concurrent use /of hydantoin anticonvulsants, succinimide anticonvulsants, barbiturates, benzodiazepines metabolized via hepatic microsomal enzymes, especially clonazepam, primidone, or valproic acid/ with carbamazepine may result in increased metabolism, leading to decreased serum concentrations and reduced elimination half-lives of these medications because of induction of hepatic microsomal enzyme activity; monitoring of blood concentrations as a guide to dosage is recommended, especially when any of these medications or carbamazepine is added to or withdrawn from an existing regimen. Valproic acid may prolong the half-life and reduce the protein-binding of carbamazepine; the concentration of the active 10,11-epoxide metabolite may be increased. In addition, use of carbamazepine in combination with other anticonvulsants has been reported to be associated with an increased risk of congenital defects and with an alteration of thyroid function. 19 9 https://pubchem.ncbi.nlm.nih.gov/compound/hydantoin PubChem Internal Link CID-10006 46 11 https://pubchem.ncbi.nlm.nih.gov/compound/succinimide PubChem Internal Link CID-11439 160 10 https://pubchem.ncbi.nlm.nih.gov/compound/clonazepam PubChem Internal Link CID-2802 172 9 https://pubchem.ncbi.nlm.nih.gov/compound/primidone PubChem Internal Link CID-4909 186 13 https://pubchem.ncbi.nlm.nih.gov/compound/valproic%20acid PubChem Internal Link CID-3121 206 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 530 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 595 13 https://pubchem.ncbi.nlm.nih.gov/compound/Valproic%20acid PubChem Internal Link CID-3121 669 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 779 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Interactions (Complete) data for CARBAMAZEPINE (41 total), please visit the HSDB record page. 85 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Interactions-(Complete) 42 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Antidote and Emergency Treatment Information on antidote and emergency treatment when exposed to this chemical. The information here is from the Hazardous Substances Data Bank (HSDB). https://pubchem.ncbi.nlm.nih.gov/source/11933 59 PEER REVIEWED Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 149 Emergency and supportive measures. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat seizures, coma, hyperthermia, arrhythmias, hyponatremia, and dystonias if they occur. Asymptomatic patients should be observed for a minimum of 6 hours after ingestion and for at least 12 hours if an extended-release preparation was ingested. ... 120 6 https://pubchem.ncbi.nlm.nih.gov/element/Oxygen PubChem Internal Link Element-Oxygen 59 PEER REVIEWED Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 150 Decontamination. Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. For massive ingestions of carbamazepine, consider additional doses of activated charcoal and possibly whole-bowl irrigation. 38 8 https://pubchem.ncbi.nlm.nih.gov/compound/charcoal PubChem Internal Link CID-5462310 165 8 https://pubchem.ncbi.nlm.nih.gov/compound/charcoal PubChem Internal Link CID-5462310 223 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 277 8 https://pubchem.ncbi.nlm.nih.gov/compound/charcoal PubChem Internal Link CID-5462310 59 PEER REVIEWED Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 150 Repeat-dose activated charcoal is effective for carbamazepine and may increase clearance by up to 50%. However, it may be difficult to perform safely in a patient with obtundation and ileus, and there is no demonstrated benefit in terms of morbidity or mortality. 22 8 https://pubchem.ncbi.nlm.nih.gov/compound/charcoal PubChem Internal Link CID-5462310 48 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 150 Plasma exchange has been used in children with carbamazepine poisoning. 47 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Antidote and Emergency Treatment (Complete) data for CARBAMAZEPINE (16 total), please visit the HSDB record page. 105 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Antidote-and-Emergency-Treatment-(Complete) 62 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Human Toxicity Excerpts Excerpts about human toxicity of this compound, extracted from authoritative documents, such as journal articles, government reports, and reference books. 59 PEER REVIEWED PMID:15046269 Wide K et al; Acta Paediatr 93 (2): 174-6 (2004) /HUMAN EXPOSURE STUDIES/ ... Infants exposed to antiepileptic drugs (n = 1398) in early pregnancy were identified from the Swedish Medical Birth Registry. The number of infants with congenital malformations and exposed to antiepileptic drug was compared with the expected number estimated from all infants born (n = 582656). 90% (1256) of the antiepileptic drug exposed children were exposed to antiepileptic drugs in monotherapy, 56% were exposed to carbamazepine and 21% to valproic acid. The odds ratio (OR) for having a malformation in the antiepileptic drug exposed group was 1.86 [95% confidence interval (95% CI) 1.42-2.44]. Exposure to valproic acid in monotherapy compared with carbamazepine in monotherapy gave OR = 2.51 (95% CI 1.43-4.68) for a neonatal diagnosis of malformations. However, there is no information available on the number of therapeutic abortions, or the different types of epilepsy or drug dosage in the two treatment groups. There was a small increase in the risk of having a major malformation after exposure to antiepileptic drugs in monotherapy. Exposure to valproic acid seems to carry a higher risk than exposure to carbamazepine. 451 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 476 13 https://pubchem.ncbi.nlm.nih.gov/compound/valproic%20acid PubChem Internal Link CID-3121 644 13 https://pubchem.ncbi.nlm.nih.gov/compound/valproic%20acid PubChem Internal Link CID-3121 688 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1092 13 https://pubchem.ncbi.nlm.nih.gov/compound/valproic%20acid PubChem Internal Link CID-3121 1152 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:11934528 Matalon S et al; Reprod Toxicol 16 (1): 9-17 (2002) /HUMAN EXPOSURE STUDIES/ ... In order to quantify ... the risks of exposure to carbamazepine during pregnancy, ... data from prospective studies ... prospective studies involving 1255 cases of exposure /were pooled/ ... Carbamazepine therapy increased the rate of congenital anomalies, mainly neural tube defects, cardiovascular and urinary tract anomalies, and cleft palate. ... Carbamazepine also appears to reduce gestational age at delivery. A combination of carbamazepine with other antiepileptic drugs is more teratogenic than carbamazepine monotherapy. Children born to untreated epileptic women do not appear to have an increased rate of major birth defects. In light of these results, we recommend performing a level 2 ultrasound and fetal echocardiography in women treated with carbamazepine during pregnancy. 79 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 220 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 380 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 463 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 533 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 788 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:7509419 Scolnik D et al; JAMA 271 (10): 767-70 (1994) /HUMAN EXPOSURE STUDIES/ Thirty-six mother-child pairs exposed to carbamazepine monotherapy and 34 pairs exposed to phenytoin monotherapy, all prospectively studied, were compared with another-child pairs exposed to nonteratogens. The controls were matched for maternal age, time of consultation, obstetric history. and socioeconomic status. The primary end point of interest was the children's global IQ measured by either the Bayley or the McCarthy scale according to their ages. ... Children exposed to phenytoin in utero had a mean (+ or - SD) global IQ 10 points lower (95% confidence interval, 4.9 to 15.8 points) than their matched controls (ll3.4 + or - 13.1 and 103.1 + or - 25.1; P = .038). The Reynell language development scores followed a similar trend, with children exposed to phenytoin scoring significantly lower than their controls. Phenytoin-exposed children had a global IQ of 84 or less significantly more often than the control group (P < .01). Children exposed in utero to carbamazepine did not differ from their controls on any of the neurobehavioral tests. /This/ study suggests a clinically important negative effect of phenytoin on neurobehavioral development, independent of maternal or environmental factors, causing a substantial number of children to achieve a lower score than expected on cognitive tests. No similar effects could be shown after gestational use of carbamazepine. 66 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 116 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 506 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 792 9 https://pubchem.ncbi.nlm.nih.gov/compound/phenytoin PubChem Internal Link CID-1775 851 9 https://pubchem.ncbi.nlm.nih.gov/compound/Phenytoin PubChem Internal Link CID-1775 59 PEER REVIEWED McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2221 /SIGNS AND SYMPTOMS/ ... Severe adverse dermatologic effects of carbamazepine include pruritic and erythematous rashes, urticaria, photosensitivity reactions, alterations in skin pigmentation, toxic epidermal necrolysis (Lyell's syndrome), and exfoliative dermatitis. In addition, erythema multiforme (including Stevens-Johnson syndrome), erythema nodosum, and development of a lupus erythematosus-like syndrome or aggravation of systemic lupus erythematosus have been reported. Alopecia may also occur. Although a causal relationship has not been established, hirsutism has been reported rarely in patients receiving carbamazepine. 64 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 618 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Human Toxicity Excerpts (Complete) data for CARBAMAZEPINE (42 total), please visit the HSDB record page. 96 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Human-Toxicity-Excerpts-(Complete) 53 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Non-Human Toxicity Excerpts Excerpts about non-human toxicity of this compound, extracted from authoritative documents, such as journal articles, government reports, and reference books. 59 PEER REVIEWED PMID:6813428 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC491572 COHN DF ET AL; J NEUROL NEUROSURG PSYCHIATRY 45 (9): 844 (1982) /LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ALBINO MALE RATS WERE INJECTED WITH CARBAMAZEPINE FOR 3 MONTHS IMMEDIATELY AFTER WEANING. A DECREASE IN PROSTATE WEIGHT WAS FOUND IN THE TREATED RATS. THEY HAD A LOWERED EPIDIDYMAL SPERM CONTENT WHICH DID NOT AFFECT THEIR FERTILITY. 97 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554 59 PEER REVIEWED Grafton TF et al; Teratology 51 (3): 185 (1995) /LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... The purpose of this study was to examine effects of carbamazepine and carbamazepine-10,11-epoxide on mouse and rat embryonic growth and development in a whole embryo culture system. Embryos were cultured in rat serum containing various concentrations of carbamazepine or carbamazepine-10,11-epoxide for 48 hr beginning on GD9 (rats) or GD8 (mice). Carbamazepine at 24 ug/mL and higher concentrations significantly increased the frequency of embryos with open anterior neural tubes among rat and mouse embryos. Effects of carbamazepine-10,11-epoxide were more variable with increases at 16, 32 and 48 (but not 24) ug/mL among rat embryos and only at 24 ug/mL among mouse embryos. Carbamazepine at 60 ug/mL significantly decreased morphological score, the number of somite pairs, DNA content, crown-rump and head lengths among rat embryos and the morphological score of mouse embryos; whereas, carbamazepine-10,11-epoxide had few such adverse effects. ... 117 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 135 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 319 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 336 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 413 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 586 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 744 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 957 27 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine-10%2C11-epoxide PubChem Internal Link CID-2555 59 PEER REVIEWED PMID:14981399 Rayburn WF et al; Am J Obstet Gynecol 190 (2): 517-21 (2004) /LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... Twenty-eight C3H/He mice were assigned randomly to treatment groups that were given food that contained either carbamazepine (25 mg in 10 g food) or a placebo for 1 week before mating and throughout gestation. Adult offspring from eight litters of each group were evaluated for standard tasks for motor, arousal/motivation, anxiety, and cognition. Statistical comparisons included analysis of variance and the Fisher exact test. Compared with the placebo group, there were no significant differences among the carbamazepine offspring in the duration of gestation, litter size, and birth weights. Fewer locomotor chamber movements were recorded in the carbamazepine group than in the placebo-exposed group at postnatal day 21 (469 vs 555 counts for 60 minutes, P<0.03) and as adults (510 vs 688 counts for 60 minutes, P<0.03) Coordination, balance, and exploratory behavior did not differ between exposure groups. A startle response from auditory arousal was decreased in carbamazepine-exposed adults (1.4% vs 21.9%, P<0.03). Performances on anxiety/motivation tasks and on learning/memory tasks revealed no significant differences between exposure groups. Although prenatal exposure induced subtle arousal effects and slower locomotor activity, carbamazepine did not have an impact on coordination, cognition, or responses to anxiety-provoking conditions. Correlation in humans is recommended. 176 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 575 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 716 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:14749669 Christensen HD et al; Am J Obstet Gynecol 190 (1): 259-63 (2004) /LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... Adult C3H/He mice were given carbamazepine in rodent chow in either a 0.25% or a 1.0% mixture. Comparisons between doses included nongravid weight change, plasma drug steady-state concentrations, and response to a maximal electroshock seizure test. The strain was then fed either the preferred dose of carbamazepine or a placebo 1 week before starting to mate and throughout gestation to compare reproductive performance and offspring early development. Mice who ate the 0.25% carbamazepine mixture displayed no evoked seizure activity and, in contrast to the 1.0% mixture, did not lose weight. This daily dose of 542+/ or - 35 mg/kg produced a trough steady-state plasma concentration that was consistent with a protective threshold in humans. Differences from placebo controls were not statistically significant for the number of cycles necessary to conceive or for the duration of gestation. The litter size, survival rates, birth weights, weight gain, and onset of eye openings and teeth eruptions of the pups were not statistically significant between the two groups. Long-term prenatal exposure to a subtoxic yet therapeutic dose of carbamazepine did not impair reproductive performance or early growth and development of exposed mice offspring. 95 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 368 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 543 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1205 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED For more Non-Human Toxicity Excerpts (Complete) data for CARBAMAZEPINE (11 total), please visit the HSDB record page. 100 16 https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019#section=Non-Human-Toxicity-Excerpts-(Complete) 57 13 https://pubchem.ncbi.nlm.nih.gov/compound/CARBAMAZEPINE PubChem Internal Link CID-2554

Ecotoxicity Excerpts Excerpts about ecotoxicity of this compound, extracted from authoritative documents, such as journal articles, government reports, and reference books. 59 PEER REVIEWED PMID:16177879 Oetken M et al; Arch Environ Contam Toxicol 49 (3): 353-61 (2005) /AQUATIC SPECIES/ The effects of the antiepileptic drug carbamazepine were studied in three freshwater invertebrate species representing different taxonomic groups, life histories, and habitats in aquatic ecosystems. The oligochaete Lumbriculus variegatus was exposed by way of carbamazepine-spiked sediments at nominal concentrations between 0.625 and 10 mg/kg dry weight (dw) for 28 days. At the end of the test, reproduction and biomass were monitored as end points. The non-biting midge Chironomus riparius was exposed to carbamazepine in a series of tests at nominal carbamazepine concentrations in sediment ranging from 0.16 to 100 mg/kg dw at 20 degrees C and 23 degrees C. Emergence and gender ratio were monitored at the end of the test. The freshwater snail Potamopyrgus antipodarum as the third test species was used in a chronic reproduction test for 28 days at aqueous carbamazepine concentrations from 0.4 to 250 mg/L. Whereas for the oligochaete and the snail no effects were observed, C. riparius exhibited a significant and concentration-dependent decrease of emergence in all test series. No observed effect concentrations and 10% effect concentrations were in the range of 33 to 140 and 70 to 210 microg/kg dw, respectively, based on measured carbamazepine concentrations in sediments. These low values indicate that carbamazepine may pose a potential threat for the survival of C. riparius and probably also for other aquatic insect populations in the field. 56 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 278 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 526 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 572 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 882 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1262 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1336 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:17223195 Kim Y et al; Environ Int 33 (3): 370-5 (2007) /AQUATIC SPECIES/ In this study, the four most abundantly used pharmaceuticals in Korea, namely acetaminophen, carbamazepine, cimetidine, and diltiazem, and six sulfonamide related antibiotics, ... were examined for their acute aquatic toxicity employing a marine bacterium (Vibrio fischeri), a freshwater invertebrate (Daphnia magna), and the Japanese medaka fish (Oryzias latipes). In general, Daphnia was the most susceptible among the test organisms. The most acutely toxic among the chemicals tested in this study was diltiazem, with a median lethal concentration of 8.2 mg/L for D. magna. ... 96 13 https://pubchem.ncbi.nlm.nih.gov/compound/acetaminophen PubChem Internal Link CID-1983 111 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 126 10 https://pubchem.ncbi.nlm.nih.gov/compound/cimetidine PubChem Internal Link CID-2756 142 9 https://pubchem.ncbi.nlm.nih.gov/compound/diltiazem PubChem Internal Link CID-39186 523 9 https://pubchem.ncbi.nlm.nih.gov/compound/diltiazem PubChem Internal Link CID-39186 59 PEER REVIEWED PMID:16528693 Lurling M et al; Environ Toxicol 21 (2): 172-80 (2006) /AQUATIC SPECIES/ The effects of the antiepileptic, analgesic drug carbamazepine on the growth, morphology, and life-history characteristics of Daphnia pulex were examined at nominal concentrations of 0, 0.1, 1, 10, 100, and 200 ug L(-1). At 1 microg carbamazepine L(-1), Daphnia matured and reproduced slightly earlier than did controls, and at a given body length females produced more offspring than did controls or those receiving other treatments. In combination with a relatively high juvenile somatic growth rate and highest total number of progeny produced per female, carbamazepine at 1ug L(-1) seemed to exert a stimulatory effect. The rates of population growth of the 100 and 200 ug L(-1) treatment groups was 9% and 32% lower, respectively, than the rates of growth of the controls and the Daphnia receiving treatments of up to 10 microg carbamazepine L(-1). At the highest dose, retardation of juvenile somatic growth resulted in delayed maturity and consequently in a lower rate of population growth. Adult somatic growth, spine length, reproductive output, and size of newborns were similar among treatments. Male offspring were only produced in the third broods, with broods that were 8% and 28% male at 1 and 10 ug L(-1), respectively. Neck teeth were never observed in Daphnia. Chronic adverse effects of carbamazepine on nontarget Daphnia were detected at 200 ug carbamazepine L(-1), but stimulatory effects might occur at environmentally realistic concentrations. However, additional studies of chronic toxicity investigating various combinations of pharmaceuticals and various environmental stresses, such as food condition, temperature, and kairomones, are needed to fully explore potential long-term adverse effects and to assess the environmental risk of common pharmaceuticals. 67 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 251 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 577 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 851 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1324 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1383 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:14599440 Jos A et al; Toxicol In Vitro 17 (5-6):525-32 (2003) /AQUATIC SPECIES/ ... Carbamazepine, an anticonvulsant commonly present in surface and groundwater, was studied, using six ecotoxicological model systems with eighteen endpoints evaluated at different exposure time periods. The battery included the immobilization of Daphnia magna, bioluminescence inhibition in the bacterium Vibrio fischeri, growth inhibition of the alga Chlorella vulgaris, and micronuclei induction and root growth inhibition in the plant Allium cepa. Cell morphology, neutral red uptake, total protein content, MTS metabolization, lactate dehydrogenase leakage and activity and glucose-6-phosphate dehydrogenase activity were studied in the salmonid fish cell line RTG-2. The total protein content, LDH activity, neutral red uptake and MTT metabolization in Vero monkey kidney cells were also investigated. The most sensitive system to carbamazepine was the Vero cell line, followed by Chlorella vulgaris, Vibrio fischeri, Daphnia magna, Allium cepa, and RTG-2 cells. EC50 values from 19 microM in Vero cells at 72 h to more than 1200 microM in other systems, were obtained. Comparing the concentrations in water and the toxicity quantified in our assay systems, carbamazepine is not expected to produce acute toxic effects in the aquatic biota under these circumstances, but chronic and synergistic effects with other chemicals cannot be excluded. 22 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 489 11 https://pubchem.ncbi.nlm.nih.gov/compound/neutral%20red PubChem Internal Link CID-11105 552 7 https://pubchem.ncbi.nlm.nih.gov/compound/lactate PubChem Internal Link CID-91435 599 19 https://pubchem.ncbi.nlm.nih.gov/compound/glucose-6-phosphate PubChem Internal Link CID-5958 734 11 https://pubchem.ncbi.nlm.nih.gov/compound/neutral%20red PubChem Internal Link CID-11105 857 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1128 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1184 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Populations at Special Risk People within the general population vary greatly in their sensitivity to chemical agents on an individual or mixture basis. Some segments of the general population may be at greatest risk for adverse outcomes. Well-known groups at special risk include children, women of childbearing age, the elderly and are also defined by nutritional status, occupations, contamination of local food supplies, gender and genetic inheritance. 59 PEER REVIEWED McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2222 Carbamazepine is contraindicated in patients with a history of previous bone marrow depression, acute intermittent porphyria, and/or hypersensitivity to the drug or in patients who have demonstrated sensitivity to any of the tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline, protriptyline). 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 258 13 https://pubchem.ncbi.nlm.nih.gov/compound/amitriptyline PubChem Internal Link CID-2160 273 11 https://pubchem.ncbi.nlm.nih.gov/compound/desipramine PubChem Internal Link CID-2995 286 10 https://pubchem.ncbi.nlm.nih.gov/compound/imipramine PubChem Internal Link CID-3696 298 13 https://pubchem.ncbi.nlm.nih.gov/compound/nortriptyline PubChem Internal Link CID-4543 313 13 https://pubchem.ncbi.nlm.nih.gov/compound/protriptyline PubChem Internal Link CID-4976 59 PEER REVIEWED McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2222 Carbamazepine may exacerbate seizures in some children with mixed seizure disorders. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:15276670 Monji A et al; Eur Psychiatry 19 (5): 322-3 (2004) We herein report a case of new-onset epileptic seizures induced by carbamazepine in an individual with autism spectrum disorders. ... epileptic seizures may possibly be either precipitated or exacerbated by carbamazepine especially in individuals with autism spectrum disorders. 67 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 207 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Protein Binding In this section, "protein binding" refers to the degree to which medications attach to plasma proteins (i.e., proteins within the blood, such as human serum albumin, lipoprotein, glycoprotein and globulins). A drug's efficiency may be affected by the degree to which it binds to plasma proteins. The less bound a drug is, the more efficiently it can traverse cell membranes or diffuse. 30 Carbamazepine is 75%-80% bound to plasma proteins. One pharmacokinetic study indicates that it is 72% bound to plasma proteins. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Ecological Information This section provides information to evaluate the environmental impact of the chemical if it were released to the environment. The information may include data from toxicity tests performed on aquatic and/or terrestrial organisms, where available (e.g., acute or chronic aquatic toxicity data for fish, algae, and crustaceans; toxicity data on birds, bees, and plants). This section also includes information on whether there is a potential for the chemical to persist or degrade in the environment either through biodegradation or other processes (such as oxidation or hydrolysis) as well as the concentration or amount of the chemical found in the environment (e.g., in plants, animals as well as in the atmosphere or water).

Environmental Fate/Exposure Summary This section summarizes the environmental fate/exposure of this chemical, including the natural and artificial sources of the chemical as a pollutant, its environmental fate, biodegradation, abiotic degradation, bioconcentration, etc. 59 PEER REVIEWED Carbamazepine's production and use as an anticonvulsive may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.8X10-7 mm Hg at 25 °C indicates carbamazepine will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase carbamazepine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 4 hours. Particulate-phase carbamazepine will be removed from the atmosphere by wet or dry deposition. Carbamazepine does contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, carbamazepine is expected to have moderate mobility based upon an estimated Koc of 510. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.1X10-10 atm-cu m/mole. A 7% removal rate in sewage treatment plants indicates that biodegradation is not an important environmental fate process. If released into water, carbamazepine is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. Carbamazepine was fairly persistent when tested in a field experiment using epilimnion lake water, exhibiting a half-life of 63 days. An estimated BCF of 15 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze readily under environmental conditions. The compound is susceptible to direct photolysis in water, with a half-life of approximately 1 day. Occupational exposure to carbamazepine may occur through inhalation and dermal contact with this compound at workplaces where carbamazepine is produced or used. Monitoring and use data indicate that the general population may be exposed to carbamazepine via ingestion drinking water, as well as those administered this drug, an anticonvulsive. (SRC) 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 217 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 314 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 509 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 585 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 749 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1138 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1145 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1264 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1386 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 1478 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1840 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1913 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 2014 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 2128 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 2165 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962

Artificial Pollution Sources Pollutants are emitted from a range of natural and man-made (artificial) sources. This section provides information on the artificial sources of the compound as a pollutant. 59 PEER REVIEWED (1) Ashford RD; Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publ, Ltd. p. 175 (1994) Carbamazepine's production and use as an analgesic/antiepileptic drug(1) may result in its release to the environment through various waste streams(SRC). 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Environmental Fate Environmental fate describes where this chemical goes when it gets out into the environment and how it might be chemically transformed in that process. This section may provide information on multiple types of environmental fates of the chemical (e.g., aquatic fate, terrestrial fate, and atmospheric fate). 59 PEER REVIEWED (1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Dal Pozzo A et al; Int J Pharm 50: 97-101 (1989) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990) (4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991) (5) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985) (6) Pfluger P, Dietrich DR; pp 11-17 in Pharmaceuticals in the environment. Kuemmerer K, ed., Springer, NY (2001) TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 520(SRC), determined from a log Kow of 2.45(2) and a regression-derived equation(3), indicates that carbamazepine is expected to have moderate mobility in soil(SRC). Volatilization of carbamazepine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Carbamazepine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-7 mm Hg(SRC), determined from a fragment constant method(5). A 7% removal rate in sewage treatment plants(8) suggests that biodegradation is not an important environmental fate process in soil(SRC). 181 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 265 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 478 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED (1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Doll TE, Frimmel FH; Chemosphere 52: 1757-69 (2003) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990) (4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991) (5) Doll TE, Frimmel FH; Chemosphere 52: 1757-69 (2003) (6) Franke C et al; Chemosphere 29: 1501-14 (1994) (7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999) (8) Tixier C et al; Environ Sci Technol 37: 1061-8 (2003) (9) Andreozzi R et al; Water Res 36: 2869-77 (2002) AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 510(SRC), determined from a log Kow of 2.45(2) and a regression-derived equation(3), indicates that carbamazepine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The compound is susceptible to direct photolysis in water(5). Applying carbamazepine to natural river water and subjecting this to solar radiation resulted in a half-life of 907 hours(9). According to a classification scheme(6), an estimated BCF of 15(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Carbamazepine was fairly persistent when tested in a field experiment using epilimnion lake water, exhibiting an overall elimination rate constant of 0.11 1/day; this corresponds to a half-life of 63 days(8). 177 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 272 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 494 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 513 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 544 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 836 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 928 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 59 PEER REVIEWED (1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985) (3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993) (4) Andreozzi R et al; Water Res 36: 2869-77 (2002) ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), carbamazepine, which has an estimated vapor pressure of 1.8X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase carbamazepine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), calculated from its rate constant of 8.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Carbamazepine absorbs light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). 124 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 348 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 667 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Environmental Biodegradation This section provides information on environmental biodegradation for this compound. Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. An important measure of biodegradability of wastewater is the biochemical oxygen demand (BOD), which is the amount of dissolved oxygen (DO) needed (i.e. demanded) by aerobic biological organisms to break down organic material present in a given water sample at certain temperature over a specific time period. 59 PEER REVIEWED (1) Pfluger P, Dietrich DR; pp 11-17 in Pharmaceuticals in the environment. Kuemmerer K, ed., Springer, NY (2001) (2) Mohle E, Metzger JW; in Amer Chem Soc Symp Ser 791(Pharmaceuticals and personal care products in the environment): 192-705 (2001) AEROBIC: Removal of carbamazepine in German sewage treatment plants was found to be extremely low at 7%(1). Using a batch suspension of activated sludge maintained under aerobic conditions, an initial decrease in 5.0 ug/L carbamazepine was observed in the first 15 minutes, then reached a constant level of 3.1 ug/L; 37% loss was attributed to adsorption to sludge. No metabolites were identified and no further degradation was observed(2). 20 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 222 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:12680655 (1) Tixier C et al; Environ Sci Technol 37: 1061-8 (2003) AEROBIC: Carbamazepine was fairly persistent when tested in a field experiment using Lake Greifensee epilimnion water, Switzerland, tested from August 16, 1999 through October 22, 1999(1); an overall elimination rate constant of 0.11 1/day was reported, corresponding to a half-life of 63 days(1). 9 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 112 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 59 PEER REVIEWED PMID:12322761 (1) Ternes TA et al; Environ Sci Technol 36: 3855-63 (2002) ANAEROBIC: Carbamazepine was found to be present in water samples following bank infiltration treatment under anaerobic conditions in a waterworks area in Germany(1). 11 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 52 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962

Environmental Abiotic Degradation Abiotic degradation is a process by which a chemical substance is broken down into smaller molecules by non-biotic means (e.g., hydrolysis, photolysis, and oxidation). 59 PEER REVIEWED (1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993) (2) Atkinson R, Carter WPL; Chem Rev 84: 437-70 (1984) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990) (4) Doll TE, Frimmel FH; Chemosphere 52: 1757-69 (2003) (5) Andreozzi R et al; Water Res 36: 2869-77 (2002) The rate constant for the vapor-phase reaction of carbamazepine with photochemically-produced hydroxyl radicals has been estimated as 8.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of carbamazepine with ozone has been estimated as 2.5X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 hour at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Carbamazepine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze readily under environmental conditions(3). Carbamazepine absorbs light at wavelengths >290 nm(5) and therefore may be susceptible to direct photolysis by sunlight(SRC). The compound is susceptible to direct photolysis in water, with measured rates ranging from 0.0006 1/min(4) to 5.7X10-3 1/hr, (half-life of 121 hours)(5). The presence of dissolved humic acid (5.0X10-3 g dm(-3)) resulted in an increase in the half-life to 233.7 hrs(5). Applying carbamazepine to natural river water and subjecting this to solar radiation resulted in a half-life of 907 hours(5). 50 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 403 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 422 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 654 5 https://pubchem.ncbi.nlm.nih.gov/compound/ozone PubChem Internal Link CID-24823 684 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 850 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 1028 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 1255 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 1286 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962

Environmental Bioconcentration This section provides information on environmental bioconcentration for this compound. Bioconcentration is the accumulation of a chemical in or on an organism when the source of chemical is solely water. Bioconcentration is a term that was created for use in the field of aquatic toxicology. Bioconcentration can also be defined as the process by which a chemical concentration in an aquatic organism exceeds that in water as a result of exposure to a waterborne chemical. 59 PEER REVIEWED (1) Dal Pozzo A et al; Int J Pharm 50: 97-101 (1989) (2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999) (3) Franke C et al; Chemosphere 29: 1501-14 (1994) An estimated BCF of 15 was calculated in fish for carbamazepine(SRC), using a log Kow of 2.45(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). 50 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Soil Adsorption/Mobility Sorption to soils and sediments is an important factor on the transport and fate of organic contaminants in the environment. The soil/water adsorption coefficient, also known as solid-water distribution coefficient (Kd), measures the amount of chemical substance adsorbed onto soil per amount of water. Since adsorption occurs predominantly by partition into the soil organic matter, it is more useful to normalize the Kd value to the organic carbon content of a soil and express the distribution coefficient in Koc (organic carbon normalized distribution coefficient). The greater the Kd (or Koc) value, the less likely a chemical will leach or contribute to runoff. A very high value means it is strongly adsorbed onto soil and organic matter and does not move throughout the soil. https://toxics.usgs.gov/pubs/FS-087-00/fs-087-00.pdf 59 PEER REVIEWED (1) Dal Pozzo A et al; Int J Pharm 50: 97-101 (1989) (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990) (3) Swann RL et al; Res Rev 85: 17-28 (1983) (4) Cordy GE et al; Ground Water Monit Remed 24: 58-69 (2004) The Koc of carbamazepine is estimated as 510(SRC), using a log Kow of 2.45(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that carbamazepine is expected to have moderate mobility in soil. In a soil column study using Mahall-Leveen sandy soil from an area northwest of Phoenix, AZ, carbamazepine was detected in the column leachate at a concentration of 0.116 ug/L following addition of the compound at 0.170 ug/L 20 days prior(4). 11 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 196 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 350 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554

Volatilization from Water/Soil Volatilization of chemicals from water/soil is the transfer of the chemical as a gas through the water-air or soil-air interface under environmental conditions 59 PEER REVIEWED (1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991) (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990) (3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985) The Henry's Law constant for carbamazepine is estimated as 1.1X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that carbamazepine is expected to be essentially nonvolatile. Carbamazepine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-7 mm Hg(SRC), determined from a fragment constant method(3). 29 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 177 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 234 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Environmental Water Concentrations Concentrations of this chemical in water in various stages of hydrologic cycle (e.g., drinking water, ground water, surface water, and rain/snow). 59 PEER REVIEWED (1) Ternes T; in Amer Chem Soc, Div Environ Chem., Preprint Ext Abstr, 219th ASC Natl Mtg., 40: 98-00 (2000) DRINKING WATER: Carbamazepine was detected in 1 of 12 drinking water samples collected from different facilities in Germany at a maximum concentration of 0.30 ug/L, detection limit of 0.01 ug/L(1). 9 5 https://pubchem.ncbi.nlm.nih.gov/compound/WATER PubChem Internal Link CID-962 16 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 63 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962 59 PEER REVIEWED (1) Daughton CG; in Amer Chem Soc Symp Ser 791(Pharmaceuticals and personal care products in the environment): 2-38 (2001) (2) Pfluger P, Dietrich DR; pp 11-17 in Pharmaceuticals in the environment. Kuemmerer K, ed., Springer, NY (2001) (3) Snyder SA et al; in Amer Chem Soc Symp Ser 791(Pharmaceuticals and personal care products in the environment): 116-39 (2001) (4) Heberer T; Toxicol Lett 131: 5-17 (2002) (5) Kolpin DW et al; Sci Total Environ 348: 119-130 (2004) SURFACE WATER: Carbamazepine is ubiquitous in the environment(1,2). A median concentration of 0.25 ug/L has been reported in German rivers(2). Concentrations as high as 1,075 ng/L have been detected in Berlin, Germany surface waters(4). Levels in waters samples from the Boulder Basin of Lake Mead, Nevada, sampled between 1997 and 1999 ranged from 14 to 35 ng/L(3). Carbamazepine concentrations in Iowa surface waters sampled in 2001 were (% frequency) 0.002 (4.3), 0.008 (4.3), and 0.263 (70.0) ug/L during high-flow, normal-flow, and low-flow conditions, respectively; reporting limit = 0.0107 ug/L(5). 8 5 https://pubchem.ncbi.nlm.nih.gov/compound/WATER PubChem Internal Link CID-962 15 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 367 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 59 PEER REVIEWED PMID:15212901 (1) Weigel S et al; Chemosphere 56: 583-92 (2004) SEAWATER: Carbamazepine was not detected in water from the Tromso, Norway Sound during sampling in April, 2002(1). 10 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 44 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962

Effluent Concentrations Concentration of this compound in effluent. Effluent is wastewater (treated or untreated) discharged into surface waters from a treatment plant, sewer, or industrial outfall. 59 PEER REVIEWED (1) Daughton CG; in Amer Chem Soc, ACS Symp Ser 2001, 791(Pharmaceuticals and personal care products in the environment): 2-38(2001) (2) Pfluger P, Dietrich DR; pp 11-17 in Pharmaceuticals in the environment. Kuemmerer K, ed., Springer, NY (2001) (3) Ternes T; in Amer Chem Soc, Div Environ Chem., Preprint Ext Abstr, 219th ASC Natl Mtg., 40: 98-00 (2000) (4) Tixier C et al; Environ Sci Technol 37: 1061-8 (2003) (5) Weigel S et al; Chemosphere 56: 583-92 (2004) Carbamazepine has been reported in sewage treatment plant and environmental samples(1). A median concentration of 2.1 ug/L has been reported in German sewage treatment plant effluents(2) with concentrations in these effluents as high as 6.3 ug/L(3). The maximum carbamazepine concentrations in waste water treatment plant effluents in Switzerland sampled for a period of 3 months reached 0.95 ug/L(4). A concentration of 0.27 ug/L was reported in an Asgard Norway sewer sample collected on April 18, 2002(5). 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554 262 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 300 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962

Milk Concentrations Concentrations of this compound in milk. 59 PEER REVIEWED Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 704 Carbamazepine is distributed into breast milk. Concentrations in breast milk and in the plasma of nursing infants have been reported to reach 60% of the maternal plasma concentration. 0 13 https://pubchem.ncbi.nlm.nih.gov/compound/Carbamazepine PubChem Internal Link CID-2554

Probable Routes of Human Exposure Potential way(s) in which people may come into contact with a hazardous chemical. Examples of common exposure routes are inhalation, ingestion, skin/eye contact. 59 PEER REVIEWED (1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available at https://www.cdc.gov/noes/ as of Jun 8, 2007. NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,295 workers (3.361 of these are female) are potentially exposed to carbamazepine in the US(1). Occupational exposure to carbamazepine may occur through inhalation and dermal contact with this compound at workplaces where carbamazepine is produced or used. Monitoring and use data indicate that the general population may be exposed to carbamazepine via ingestion of drinking water, as well as those administered this drug, an anticonvulsive(SRC). 132 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 185 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 286 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 400 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 440 5 https://pubchem.ncbi.nlm.nih.gov/compound/water PubChem Internal Link CID-962

Associated Disorders and Diseases Disorders and diseases associated with the compound. The contexts of the associations listed in this section vary. For example, a compound may cause its associated diseases (e.g., carcinogens and cancers) or have a therapeutic effect in treatment of the diseases (e.g., antihistamines and allergies), or be used as a marker/indicator for the diseases (e.g., glucose and diabetes). Subsections 2 Disease References Name Value 12 ctd_chemical_disease 189 collection=ttd_dd

Literature Scientific articles associated with this compound. Some chemical-literature associations in this section are provided by data contributors or derived from MeSH annotations, as explained in Kim et al., J. Cheminform. 2016, 8, 32. This section also provides the lists of chemicals, genes/proteins, and diseases, that are co-mentioned in scientific articles, as described in Zaslavsky et al., Front. Res. Metr. Anal., 2021, 6, 689059. https://pubchem.ncbi.nlm.nih.gov/docs/literature

Consolidated References The consolidated references include literature data from all sources including Springer Nature, Thieme Chemistry, Wiley, Nature journals, depositor provided citations, and NLM curated PubMed citations. https://pubchem.ncbi.nlm.nih.gov/docs/literature 199 literature

NLM Curated PubMed Citations The NLM Curated PubMed Citations section links to all PubMed records that are tagged with the same MeSH term that has been associated with a particular compound. https://jcheminf.biomedcentral.com/articles/10.1186/s13321-016-0142-6 199 https://www.ncbi.nlm.nih.gov/sites/entrez?LinkName=pccompound_pubmed_mesh&db=pccompound&cmd=Link&from_uid=2554 true

Springer Nature References Literature references related to scientific contents from Springer Nature journals and books. These references have been ranked automatically by an algorithm which calculates the relevance for each substance in a Springer Nature document. It is based on: (1) the TF-IDF, adapted to chemical structures, (2) location information in the text (e.g. title, abstract, keywords), and (3) the document size. Springer Nature aims to provide only highly qualitative and relevant content but references of lower relevance aren't withheld as they might contain also very useful information. 178 springernature

Thieme References Literature references related to scientific contents from Thieme Chemistry journals and books. The Thieme Chemistry content within this section is provided under a CC-BY-NC-ND 4.0 license (https://creativecommons.org/licenses/by-nc-nd/4.0/), unless otherwise stated. 190 Thieme References ThiemeChemistry

Wiley References Literature references related to scientific contents from Wiley journals and books. 197 wiley

Nature Journal References Literature references provided by Nature journals including Nature Chemistry, Nature Synthesis, Nature Chemical Biology, Nature Communications, Nature Catalysis, etc. 145 http://dx.doi.org/10.1038/nchem.859 Foster et al. Anion-switchable supramolecular gels for controlling pharmaceutical crystal growth. Nature Chemistry, doi: 10.1038/nchem.859, published online 10 October 2010 http://www.nature.com/nchem

Chemical Co-Occurrences in Literature Chemical co-occurrences in literature highlight chemicals mentioned together in scientific articles. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of publications and other statistics, with the most relevant mentions appearing at the top. https://doi.org/10.3389/frma.2021.689059 199 Co-Occurrence Panel ChemicalNeighbor Chemical ChemicalName_1 ChemicalName_2 SUMMARY_URL.cid CID CID

Chemical-Gene Co-Occurrences in Literature Chemical-gene co-occurrences in the literature highlight chemical-gene pairs mentioned together in scientific articles. This may suggest that an important relationship exists between the two. Note that a co-occurring gene entity is organism non-specific and could refer to a gene, protein, or enzyme. Also note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of publications and other statistics, with the most relevant mentions appearing at the top. https://doi.org/10.3389/frma.2021.689059 199 Co-Occurrence Panel ChemicalGeneSymbolNeighbor Gene/Protein/Enzyme ChemicalName GeneSymbolName https://pubchem.ncbi.nlm.nih.gov/gene/SYMBOL: CID GeneSymbol

Chemical-Disease Co-Occurrences in Literature Chemical-disease co-occurrences in literature highlight chemical-disease pairs mentioned together in scientific articles. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of publications and other statistics, with the most relevant mentions appearing at the top. https://doi.org/10.3389/frma.2021.689059 199 Co-Occurrence Panel ChemicalDiseaseNeighbor Disease ChemicalName DiseaseName https://meshb.nlm.nih.gov/record/ui?ui= CID MeSH

Patents Patent applications/documents that mention this compound. Columns 30 US5284662 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US5284662 US5912013 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US5912013 US6977253 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US6977253 US7635773 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US7635773 US8410077 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US8410077 US9493582 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US9493582 US9629797 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US9629797 US9770407 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US9770407 US9750822 0 9 https://pubchem.ncbi.nlm.nih.gov/patent/US9750822 US11529357 0 10 https://pubchem.ncbi.nlm.nih.gov/patent/US11529357

Depositor-Supplied Patent Identifiers Patent identifiers provided by data depositors, along with information on those patents. 199 patent 199 Link to all deposited patent identifiers 0 40 https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/2554/xrefs/PatentID/TXT

WIPO PATENTSCOPE Use the provided link to show patents associated with this chemical structure in WIPO's PATENTSCOPE system. https://www.wipo.int/patentscope/en/ 230 Patents are available for this chemical structure: https://patentscope.wipo.int/search/en/result.jsf?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N 0 86 https://patentscope.wipo.int/search/en/result.jsf?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N

FDA Orange Book Patents Patents listed for this chemical in the Orange Book published by U.S. Food and Drug Administration (FDA). The Orange Book identifies FDA-approved drug products and related patent and exclusivity information. https://www.fda.gov/drugs/drug-approvals-and-databases/approved-drug-products-therapeutic-equivalence-evaluations-orange-book 55 collection=fdaorgpt&query_type=synonym&query='^CARBAMAZEPINE$'

Chemical Co-Occurrences in Patents Chemical co-occurrences in patents highlight chemicals mentioned together in patent documents. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of patents and other statistics, with the most relevant mentions appearing at the top. 199 Co-Occurrence Panel PatentChemicalChemical Chemical ChemicalName NeighborName SUMMARY_URL.cid CID CID

Chemical-Disease Co-Occurrences in Patents Disease co-occurrences in patents highlight chemicals and diseases mentioned together in patent documents. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of patents and other statistics, with the most relevant mentions appearing at the top. 199 Co-Occurrence Panel PatentChemicalDisease Disease ChemicalName NeighborName https://meshb.nlm.nih.gov/record/ui?ui= CID MeSH

Chemical-Gene Co-Occurrences in Patents Gene co-occurrences in patents highlight chemicals and genes mentioned together in patent documents. This may suggest that an important relationship exists between the two. Please note that this content is not human curated. It is generated by text-mining algorithms that can be fooled such that a co-occurrence may be happenstance or a casual mention. The lists are ordered by relevancy as indicated by count of patents and other statistics, with the most relevant mentions appearing at the top. 199 Co-Occurrence Panel PatentChemicalGene Gene ChemicalName NeighborName https://pubchem.ncbi.nlm.nih.gov/gene/SYMBOL: CID GeneSymbol

Interactions and Pathways This section provides information on the biomolecular interactions of this compound with drugs, genes, proteins, etc., as well as the pathways in which this compound is involved.

Protein Bound 3D Structures Experimentally determined 3D structures of the macromolecules (e.g., proteins) that this compounds bind to. The 3D structures in this section are from multiple sources including the RCSB Protein Data Bank (PDB), PDB in Europe (PDBe), and NCBI Structure database. 167 pdb 199 https://www.ncbi.nlm.nih.gov/structure?cmd=Link&LinkName=pccompound_structure&from_uid=2554 View 2 proteins in NCBI Structure

Ligands from Protein Bound 3D Structures Ligands found in experimental protein-ligand co-complexes (e.g., those archived in the Protein Data Bank in Europe (PDBe)). https://www.ebi.ac.uk/pdbe/ Subsections 2 Name Value true 1

PDBe Ligand Code The ligand code for this compound used in the Protein Data Bank in Europe (PDBe). 165 http://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/N6W N6W

PDBe Structure Code The structure code for the Protein Data Bank in Europe (PDBe) protein-ligand co-complex from which the ligand's 3-D coordinates were taken. 165 http://www.ebi.ac.uk/pdbe/entry/pdb/6TFB 6TFB

PDBe Conformer The experimental protein-bound 3D structure of this compound in a protein-ligand co-complex archived in the Protein Data Bank in Europe (PDBe). 165 http://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/N6W https://pubchem.ncbi.nlm.nih.gov/rest/pug_view/data/key/8763156_1 pubchem/compound-gzip-asnb

Chemical-Target Interactions Interactions between targets and this compound 12 consolidatedcompoundtarget 28 consolidatedcompoundtarget 30 collection=consolidatedcompoundtarget&query_type=name&query=^Carbamazepine$ 68 consolidatedcompoundtarget 191 consolidatedcompoundtarget

Drug-Drug Interactions Drug-drug interactions for this compound. Drug-drug interactions occur when two or more drugs react with each other. This drug-drug interaction may cause you to experience an unexpected side effect. For example, mixing a drug you take to help you sleep (a sedative) and a drug you take for allergies (an antihistamine) can slow your reactions and make driving a car or operating machinery dangerous. https://www.fda.gov/drugs/resources-you-drugs/drug-interactions-what-you-should-know 30 collection=drugbankddi&query_type=name&query=^Carbamazepine$

Drug-Food Interactions Drug-food interactions for this compound. Drug-food/beverage interactions result from drugs reacting with foods or beverages. For example, mixing alcohol with some drugs may cause you to feel tired or slow your reactions. https://www.fda.gov/drugs/resources-you-drugs/drug-interactions-what-you-should-know Bulleted 30 Avoid alcohol. Ingesting alcohol may increase drowsiness and dizziness. Avoid grapefruit products. Exercise caution with St. John's Wort. This herb induces the CYP3A metabolism of carbamazepine and may reduce its serum concentration. 81 13 https://pubchem.ncbi.nlm.nih.gov/compound/carbamazepine PubChem Internal Link CID-2554 Take with or without food.

Pathways Biological pathways in which this compound is involved. 199 collection=pathway&core=1

Biological Test Results A PubChem substance or compound summary page displays biological test results from the PubChem BioAssay database, if/as available, for the chemical structure currently displayed. You can embed biological test results displays within your own web pages, for a PubChem Compound or Substance of interest, by using the BioActivity Widget. https://pubchem.ncbi.nlm.nih.gov/docs/widgets

BioAssay Results Bioactivity data for this compound, reported in PubChem BioAssay records. 199 bioactivity

Classification A set of concepts and categories in a subject area or domain that shows their properties and the relations between them.

MeSH Tree The Medical Subject Headings (MeSH) tree for this entity. MeSH is a controlled and hierarchically-organized vocabulary produced by the National Library of Medicine. https://www.nlm.nih.gov/mesh 200 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=1 1

NCI Thesaurus Tree NCI Thesaurus (NCIt) hierarchy https://ncithesaurus.nci.nih.gov 221 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=112 112

ChEBI Ontology ChEBI Ontology tree. ChEBI is an acronym for Chemical Entities of Biological Interest, which is a freely available dictionary of molecular entities focused on 'small' chemical compounds. ChEBI incorporates an ontological classification, whereby the relationships between molecular entities or classes of entities and their parents and/or children are specified. https://www.ebi.ac.uk/chebi/ 201 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=2 2

KEGG: Drug Classification/ontology tree for therapeutic categories of drugs in Japan, from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08301 202 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=14 14

KEGG: USP US Pharmacopeia (USP) drug classification tree from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08302 203 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=15 15

KEGG: ATC Anatomical Therapeutic Chemical (ATC) classification tree from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08303 204 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=16 16

KEGG: Target-based Classification of Drugs Target-based classification tree of drugs, from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08310 205 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=22 22

KEGG: JP15 Classification/ontology tree for drugs listed in the Japanese Pharmacopoeia, from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08311 206 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=23 23

KEGG: Drug Groups KEGG : Drug Groups tree 214 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=96 96

KEGG: Drug Classes Drug classes tree from the Kyoto Encyclopedia of Genes and Genomes (KEGG). https://www.genome.jp/kegg-bin/get_htext?htext=br08332 223 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=118 118

WHO ATC Classification System The Anatomical Therapeutic Chemical (ATC) Classification System is used for the classification of drugs. This pharmaceutical coding system divides drugs into different groups according to the organ or system on which they act and/or their therapeutic and chemical characteristics. Each bottom-level ATC code stands for a pharmaceutically used substance, or a combination of substances, in a single indication (or use). This means that one drug can have more than one code: acetylsalicylic acid (aspirin), for example, has A01AD05 as a drug for local oral treatment, B01AC06 as a platelet inhibitor, and N02BA01 as an analgesic and antipyretic. On the other hand, several different brands share the same code if they have the same active substance and indications. https://www.who.int/tools/atc-ddd-toolkit/atc-classification 209 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=79 79

FDA Pharm Classes Pharmacologic Class is a group of active moieties that share scientifically documented properties and is defined on the basis of any combination of three attributes of the active moiety: mechanism of action (MOA), physiologic effect (PE) and chemical structure (CS). An FDA "Established Pharmacologic Class" (EPC) text phrase is a pharmacologic class associated with an approved indication of an active moiety that the FDA has determined to be scientifically valid and clinically meaningful. https://www.fda.gov/industry/structured-product-labeling-resources/pharmacologic-class 208 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=78 78

ChemIDplus Classification of this compound, provided by ChemIDplus, which is a free web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases. ChemIDplus groups chemicals based on the source locators (i.e., what information resources have data for a given chemical). https://chem.nlm.nih.gov/chemidplus/ 211 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=84 84

IUPHAR/BPS Guide to PHARMACOLOGY Target Classification Classification of this entity in the context of targets, provided by the IUPHAR/BPS Guide to PHARMACOLOGY. https://www.guidetopharmacology.org/ 213 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=92 92

ChEMBL Target Tree Classification of this entity in the context of targets, provided by ChEMBL. https://www.ebi.ac.uk/chembl/ 212 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=87 87

UN GHS Classification The United Nations' Globally Harmonized System of Classification and Labelling of Chemicals (GHS) provides a harmonized basis for globally uniform physical, environmental, and health and safety information on hazardous chemical substances and mixtures. https://unece.org/about-ghs 210 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=83 83

EPA CPDat Classification Classification from the U.S. Environmental Protection Agency's CPDat (Chemical and Products Database). This database contains information mapping more than 49,000 chemicals to a set of terms categorizing their usage or function in 16,000 consumer products (e.g. shampoo, soap) types based on what chemicals they contain. https://www.epa.gov/chemical-research/chemical-and-products-database-cpdat 215 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=99 99

NORMAN Suspect List Exchange Classification A classification from the NORMAN Suspect List Exchange, which serve as a central access point to find lists of chemicals with environmental concerns. https://www.norman-network.com/nds/SLE/ 216 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=101 101

CCSBase Classification CCSbase is an integrated platform that contains collision cross section data for the compound. The CCSbase classification groups the compounds by the type of adduct ions that can be formed from them (e.g., [M-H]-, [M+H]+, [M+Na]+, [M+K]+). https://ccsbase.net/ 217 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=104 104

EPA DSSTox Classification Classification from the U.S. Environmental Protection Agency's Distributed Structure-Searchable Toxicity (DSSTox) database. DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. A distinguishing feature of this effort is the accurate mapping of bioassay and physicochemical property data associated with chemical substances to their corresponding chemical structures. https://www.epa.gov/chemical-research/distributed-structure-searchable-toxicity-dsstox-database 218 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=105 105

FDA Drug Type and Pharmacologic Classification The FDA Drug Type and Pharmacologic Classification is based on the FDA drug type and pharm classes data from the National Drug Code (NDC) Directory. 222 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=116 116

EPA Substance Registry Services Tree Substance Registry Services (SRS) is the Environmental Protection Agency's (EPA) central system for information about substances that are tracked or regulated by EPA or other sources. It is a resource for basic information about chemicals, biological organisms, and other substances of interest to EPA and its state and tribal partners. SRS makes it possible to identify which EPA data systems, environmental statutes, or other sources have information about a substance and which synonym is used by that system or statute. 224 HID https://pubchem.ncbi.nlm.nih.gov/classification/#hid=123 123

1 Burnham Center for Chemical Genomics SID855967 SID855967 Aqueous solubility in buffer at pH 7.4 https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table 694543 59 Hazardous Substances Data Bank (HSDB) 3019 CARBAMAZEPINE The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3019 https://www.nlm.nih.gov/web_policies.html true 2202 60 Human Metabolome Database (HMDB) HMDB0014704 Carbamazepine The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. http://www.hmdb.ca/metabolites/HMDB0014704 HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 2151187 2 CAS Common Chemistry 298-46-4 Carbamazepine CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. https://commonchemistry.cas.org/detail?cas_rn=298-46-4 The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. https://creativecommons.org/licenses/by-nc/4.0/ 12813022 9 ChemIDplus 0000298464 Carbamazepine [USAN:USP:INN:BAN:JAN] ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000298464 https://www.nlm.nih.gov/copyright.html true 768680 30 DrugBank DB00564 Carbamazepine The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. https://www.drugbank.ca/drugs/DB00564 Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) https://www.drugbank.ca/legal/terms_of_use 3603988 43 DTP/NCI NSC 755920 carbamazepine The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=755920 Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. https://www.cancer.gov/policies/copyright-reuse 6608850 44 DTP/NCI NSC 169864 carbamazepine The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=169864 Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. https://www.cancer.gov/policies/copyright-reuse 6752104 46 EPA DSSTox DTXSID4022731 Carbamazepine DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. https://comptox.epa.gov/dashboard/DTXSID4022731 https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 1150909 49 European Chemicals Agency (ECHA) 206-062-7 Carbamazepine The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. https://echa.europa.eu/substance-information/-/substanceinfo/100.005.512 Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. https://echa.europa.eu/web/guest/legal-notice 2007064 50 FDA Global Substance Registration System (GSRS) 33CM23913M CARBAMAZEPINE The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/33CM23913M Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 5865322 147 New Zealand Environmental Protection Authority (EPA) 1bf178bdcbadd4924a05c7bf93b43dde Carbamazepine The New Zealand Environmental Protection Authority is a government agency for regulating activities that affect Aotearoa New Zealand's environment. https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/ This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence. https://www.epa.govt.nz/about-this-site/general-copyright-statement/ 37149928 3 CCSbase 2537843204 CARBAMAZEPINE CCSbase curates experimental collision cross section values measured on various ion mobility platforms as a resource for the research community. CCSbase also builds prediction models for comprehensive prediction of collision cross sections for a given molecule. 38986595 4 CCSbase 1592408298 Carbamazepine CCSbase curates experimental collision cross section values measured on various ion mobility platforms as a resource for the research community. CCSbase also builds prediction models for comprehensive prediction of collision cross sections for a given molecule. 38989545 5 CCSbase 3242329220 CARBAMAZEPINE CCSbase curates experimental collision cross section values measured on various ion mobility platforms as a resource for the research community. CCSbase also builds prediction models for comprehensive prediction of collision cross sections for a given molecule. 38989654 6 CCSbase 2551828978 CARBAMAZEPINE CCSbase curates experimental collision cross section values measured on various ion mobility platforms as a resource for the research community. CCSbase also builds prediction models for comprehensive prediction of collision cross sections for a given molecule. 38993556 163 NORMAN Suspect List Exchange nrm_2554 carbamazepine The NORMAN network enhances the exchange of information on emerging environmental substances, and encourages the validation and harmonisation of common measurement methods and monitoring tools so that the requirements of risk assessors and risk managers can be better met. The NORMAN Suspect List Exchange (NORMAN-SLE) is a central access point to find suspect lists relevant for various environmental monitoring questions, described in DOI:10.1186/s12302-022-00680-6 Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0 https://creativecommons.org/licenses/by/4.0/ 9030737 7 ChEBI CHEBI:OBO:2554 Carbamazepine Chemical Entities of Biological Interest (ChEBI) is a database and ontology of molecular entities focused on 'small' chemical compounds, that is part of the Open Biomedical Ontologies effort. The term "molecular entity" refers to any constitutionally or isotopically distinct atom, molecule, ion, ion pair, radical, radical ion, complex, conformer, etc., identifiable as a separately distinguishable entity. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3387 2463502 58 FDA Pharm Classes 33CM23913M CARBAMAZEPINE FDA Pharmacologic class is a group of active moieties that share scientifically documented properties and is defined on the basis of any combination of attributes of the active moiety. Read more at https://www.fda.gov/industry/structured-product-labeling-resources/pharmacologic-class https://dailymed.nlm.nih.gov/dailymed/browse-drug-classes.cfm Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 13206756 73 LiverTox Carbamazepine Carbamazepine LIVERTOX provides up-to-date, accurate, and easily accessed information on the diagnosis, cause, frequency, patterns, and management of liver injury attributable to prescription and nonprescription medications, herbals and dietary supplements. https://www.ncbi.nlm.nih.gov/books/n/livertox/Carbamazepine/ https://www.nlm.nih.gov/copyright.html true 2261754 146 NCI Thesaurus (NCIt) C341::Compound NCI Thesaurus (NCIt), from the U.S. National Cancer Institute, provides reference terminology for many NCI and other systems. It covers vocabulary for clinical care, translational and basic research, and public information and administrative activities. https://ncithesaurus.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=ncit&code=C341 Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. https://www.cancer.gov/policies/copyright-reuse 14395658 191 Toxin and Toxin Target Database (T3DB) Compound::T3D2826 Carbamazepine The Toxin and Toxin Target Database (T3DB), or, soon to be referred as, the Toxic Exposome Database, is a unique bioinformatics resource that combines detailed toxin data with comprehensive toxin target information. http://www.t3db.ca/toxins/T3D2826 T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication. http://www.t3db.ca/downloads 20442679 8 ChEMBL Compound::CHEMBL108 ChEMBL or ChEMBLdb is a manually curated chemical database of bioactive molecules with drug-like properties. It is maintained by the European Bioinformatics Institute (EBI), of the European Molecular Biology Laboratory (EMBL), based at the Wellcome Trust Genome Campus, Hinxton, UK. https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL108/ Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/). http://www.ebi.ac.uk/Information/termsofuse.html 31239562 10 ChemIDplus r_135269948 The toxicity data was from the legacy RTECS data set in ChemIDplus. https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000298464 https://www.nlm.nih.gov/copyright.html true 19571056 11 ClinicalTrials.gov cid2554 ClinicalTrials.gov is an NIH registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. https://clinicaltrials.gov/ The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use. https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use 5186299 12 Comparative Toxicogenomics Database (CTD) D002220::Compound Carbamazepine CTD is a robust, publicly available database that aims to advance understanding about how environmental exposures affect human health. https://ctdbase.org/detail.go?type=chem&acc=D002220 It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University. http://ctdbase.org/about/legal.jsp 9023446 28 Drug Gene Interaction database (DGIdb) rxcui:2002 CARBAMAZEPINE The Drug Gene Interaction Database (DGIdb, www.dgidb.org) is a web resource that consolidates disparate data sources describing drug - gene interactions and gene druggability. https://www.dgidb.org/drugs/rxcui:2002 The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section. http://www.dgidb.org/downloads 37459163 68 IUPHAR/BPS Guide to PHARMACOLOGY 5339::Compound carbamazepine The IUPHAR database contains quantitative information on drug targets and the prescription medicines and experimental drugs that act on them. All entries in BioAssay data are marked as active as our curation SOP means we only extract data from the literature for relatively potent compounds. https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=5339 The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/) https://www.guidetopharmacology.org/about.jsp#license 19629881 189 Therapeutic Target Database (TTD) D04MSM Carbamazepine Therapeutic Target Database (TTD) is a database to provide information about the known and explored therapeutic protein and nucleic acid targets, the targeted disease, pathway information and the corresponding drugs directed at each of these targets. https://idrblab.net/ttd/data/drug/details/D04MSM 19766844 13 Crystallography Open Database (COD) 2107460 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/2107460.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30618783 14 Crystallography Open Database (COD) 2300327 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/2300327.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30655266 15 Crystallography Open Database (COD) 2311081 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/2311081.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30655626 16 Crystallography Open Database (COD) 2311083 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/2311083.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30655628 17 Crystallography Open Database (COD) 4509215 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4509215.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30729906 18 Crystallography Open Database (COD) 4509220 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4509220.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30729910 19 Crystallography Open Database (COD) 4509221 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4509221.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30729911 20 Crystallography Open Database (COD) 4509222 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4509222.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30729912 21 Crystallography Open Database (COD) 4510731 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4510731.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30730464 22 Crystallography Open Database (COD) 4510732 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4510732.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30730465 23 Crystallography Open Database (COD) 4510733 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/4510733.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30730466 24 Crystallography Open Database (COD) 7106548 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/7106548.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30768396 25 Crystallography Open Database (COD) 7227180 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. https://www.crystallography.net/cod/7227180.html All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30796710 26 Crystallography Open Database (COD) CID 2554 The Crystallography Open Database is an open-access collection of crystal structures of organic, inorganic, metal-organic compounds, and minerals, excluding biopolymers. All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data. https://creativecommons.org/publicdomain/zero/1.0/ 30811451 180 The Cambridge Structural Database CCDC 185919 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=185919 3319280 181 The Cambridge Structural Database CCDC 249934 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=249934 3331437 182 The Cambridge Structural Database CCDC 609185 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=609185 3342954 183 The Cambridge Structural Database CCDC 635853 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=635853 3348366 184 The Cambridge Structural Database CCDC 791775 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=791775 3378436 185 The Cambridge Structural Database CCDC 814268 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=814268 3382620 186 The Cambridge Structural Database CCDC 960316 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=960316 3407123 187 The Cambridge Structural Database CCDC 960317 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=960317 3407124 188 The Cambridge Structural Database CCDC 960318 The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffraction techniques. https://www.ccdc.cam.ac.uk/structures/Search?Ccdcid=960318 3407125 27 DailyMed 1b59ec2aa96e72402f439b14db730ab2 CARBAMAZEPINE The U.S. National Library of Medicine's DailyMed provides trustworthy information about marketed drugs. DailyMed is the official provider of FDA label information (package inserts). https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=CARBAMAZEPINE https://www.nlm.nih.gov/copyright.html 30959375 29 Drug Induced Liver Injury Rank (DILIrank) Dataset LT00060 carbamazepine Drug-Induced Liver Injury Rank (DILIrank) Dataset is a list of drugs ranked by their risk for developing DILI in humans. https://www.fda.gov/science-research/liver-toxicity-knowledge-base-ltkb/drug-induced-liver-injury-rank-dilirank-dataset Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 12652141 31 Drugs and Lactation Database (LactMed) LM400 Carbamazepine The LactMed(R) database contains information on drugs and other chemicals to which breastfeeding mothers may be exposed. https://www.ncbi.nlm.nih.gov/books/NBK501922/ https://www.ncbi.nlm.nih.gov/books/n/lactmed/LM400/ https://www.nlm.nih.gov/copyright.html 24796922 140 Mother To Baby Fact Sheets carbamazepine carbamazepine The MotherToBaby Fact Sheets answer frequently asked questions about many common exposures during pregnancy and breastfeeding, including medications, recreational substances, cosmetic treatments, health conditions, infections, vaccines, and more. https://www.ncbi.nlm.nih.gov/books/n/mtb/carbamazepine-en/ Copyright by OTIS. This work is available under the Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported license (CC BY-NC-ND 3.0). https://www.ncbi.nlm.nih.gov/books/about/copyright/ 30371805 32 Drugs@FDA c5bc9ef0658e62a37e92c5f746db4806 EPITOL Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38964520 33 Drugs@FDA 1b59ec2aa96e72402f439b14db730ab2 CARBAMAZEPINE Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38964561 34 Drugs@FDA 798b10ae2ca78678c21692eebc364339 TEGRETOL Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38968821 35 Drugs@FDA 4acc7407aa07e701b4d86537a15d390a TEGRETOL-XR Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38970574 36 Drugs@FDA 84534c0531c1b534b57dc20fa397b238 CARBATROL Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38971293 37 Drugs@FDA 5bfc8c756bcc0edaa5308c61074cf502 EPITOL Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38971634 38 Drugs@FDA ae24c84b375bbe11f68840cc66b54567 CARBAMAZEPINE Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38971654 39 Drugs@FDA 37d31444281bdaa6f3e2eb00e62ced13 TERIL Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38974319 40 Drugs@FDA d1a22ef9eef59ba36105401ecef9c624 CARNEXIV Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38977050 41 Drugs@FDA 1b6e682c01bcba498469be419adc6ee5 TEGRETOL Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38977396 42 Drugs@FDA 2a483bf705fc104c7f53d165f71a270b EQUETRO Drugs@FDA includes most of the drug products approved for human use since 1939. This includes prescription, generic, over-the-counter and therapeutic biological products. The majority of patient information, labels, approval letters and reviews are available for drug products approved since 1998. https://www.accessdata.fda.gov/scripts/cder/daf/ Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 38978135 45 EPA Chemical and Products Database (CPDat) 12525_DTXSID4022731 The US EPA Chemical and Products Database (CPDat) is a database containing information mapping more than 49,000 chemicals to a set of terms categorizing their usage or function in 16,000 consumer products (e.g. shampoo, soap) types based on what chemicals they contain. https://comptox.epa.gov/dashboard/DTXSID4022731#exposure https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 13735460 47 EU Clinical Trials Register cid2554 The EU Clinical Trials Register contains information on interventional clinical trials on medicines conducted in the European Union (EU), or the European Economic Area (EEA) which started after 1 May 2004. https://www.clinicaltrialsregister.eu/ 6479057 48 European Chemicals Agency (ECHA) 27286 Carbamazepine The information provided here is aggregated from the "Notified classification and labelling" from ECHA's C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/27286 Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. https://echa.europa.eu/web/guest/legal-notice 1859014 51 FDA Medication Guides Carbatrol Carbatrol FDA Medication Guides are paper handouts that come with many prescription medicines. The guides address issues that are specific to particular drugs and drug classes, and they contain FDA-approved information that can help patients avoid serious adverse events. https://www.fda.gov/Drugs/DrugSafety/ucm085729.htm https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=medguide.page Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 2141287 52 FDA Medication Guides Equetro Equetro FDA Medication Guides are paper handouts that come with many prescription medicines. The guides address issues that are specific to particular drugs and drug classes, and they contain FDA-approved information that can help patients avoid serious adverse events. https://www.fda.gov/Drugs/DrugSafety/ucm085729.htm https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=medguide.page Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 2141356 53 FDA Medication Guides Tegretol Tegretol FDA Medication Guides are paper handouts that come with many prescription medicines. The guides address issues that are specific to particular drugs and drug classes, and they contain FDA-approved information that can help patients avoid serious adverse events. https://www.fda.gov/Drugs/DrugSafety/ucm085729.htm https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=medguide.page Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 5789463 54 FDA Medication Guides Tegretol-XR Tegretol-XR FDA Medication Guides are paper handouts that come with many prescription medicines. The guides address issues that are specific to particular drugs and drug classes, and they contain FDA-approved information that can help patients avoid serious adverse events. https://www.fda.gov/Drugs/DrugSafety/ucm085729.htm https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=medguide.page Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 5789464 55 FDA Orange Book 311e6f58532074cd5ffa125235929f9f CARBAMAZEPINE The publication, Approved Drug Products with Therapeutic Equivalence Evaluations (the List, commonly known as the Orange Book), identifies drug products approved on the basis of safety and effectiveness by the Food and Drug Administration (FDA) under the Federal Food, Drug, and Cosmetic Act (the Act). https://www.fda.gov/drugs/drug-approvals-and-databases/approved-drug-products-therapeutic-equivalence-evaluations-orange-book Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 35234343 56 FDA Orange Book 0ee563a4db9611dc6dbd7b824753737f EPITOL The publication, Approved Drug Products with Therapeutic Equivalence Evaluations (the List, commonly known as the Orange Book), identifies drug products approved on the basis of safety and effectiveness by the Food and Drug Administration (FDA) under the Federal Food, Drug, and Cosmetic Act (the Act). https://www.fda.gov/drugs/drug-approvals-and-databases/approved-drug-products-therapeutic-equivalence-evaluations-orange-book Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 35235220 57 FDA Orange Book 1d6973c003ec3f0663514be571d8a4f4 TEGRETOL The publication, Approved Drug Products with Therapeutic Equivalence Evaluations (the List, commonly known as the Orange Book), identifies drug products approved on the basis of safety and effectiveness by the Food and Drug Administration (FDA) under the Federal Food, Drug, and Cosmetic Act (the Act). https://www.fda.gov/drugs/drug-approvals-and-databases/approved-drug-products-therapeutic-equivalence-evaluations-orange-book Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 35238060 144 National Drug Code (NDC) Directory 965e0d1eaffa54528a4ee820d8d71ba7 CARBAMAZEPINE The National Drug Code (NDC) is a unique, three-segment number that serves as FDA's identifier for drugs. The NDC Directory contains information on active and certified finished and unfinished drugs submitted to FDA. https://www.fda.gov/drugs/drug-approvals-and-databases/national-drug-code-directory Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 31085800 74 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_1 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13616395 123 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_50 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257757 124 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_51 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257758 136 MassBank of North America (MoNA) LibGen000211 Carbmazepine_major MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 44 MS data records(44 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FFGPTBGBLSHEPO-UHFFFAOYSA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 37384224 137 MassBank of North America (MoNA) LibGen000165 Carbmazepine_major MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 44 MS data records(44 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FFGPTBGBLSHEPO-UHFFFAOYSA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 37384267 138 MassBank of North America (MoNA) LibGen000164 Carbmazepine_minor MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 44 MS data records(44 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FFGPTBGBLSHEPO-UHFFFAOYSA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 37384268 61 Human Metabolome Database (HMDB) HMDB0014704_nmr_one_2324 HMDB0014704_nmr_one_2324 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 15340242 177 SpectraBase 12aC1lu8DXK Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/12aC1lu8DXK 13594817 62 Human Metabolome Database (HMDB) HMDB0014704_msms_2226189 HMDB0014704_msms_2226189 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 19277176 63 Human Metabolome Database (HMDB) HMDB0014704_msms_2228533 HMDB0014704_msms_2228533 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 19277177 64 Human Metabolome Database (HMDB) HMDB0014704_msms_2228583 HMDB0014704_msms_2228583 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 19277178 65 Human Metabolome Database (HMDB) HMDB0014704_msms_2230845 HMDB0014704_msms_2230845 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 19277179 66 Human Metabolome Database (HMDB) HMDB0014704_msms_2231046 HMDB0014704_msms_2231046 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 19277180 67 Human Metabolome Database (HMDB) HMDB0014704_msms_2231288 HMDB0014704_msms_2231288 The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. https://hmdb.ca/metabolites/HMDB0014704#spectra HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. http://www.hmdb.ca/citing 19277181 157 NIST Mass Spectrometry Data Center MS-MS #1 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 284843 158 NIST Mass Spectrometry Data Center MS-MS #2 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 284902 159 NIST Mass Spectrometry Data Center MS-MS #3 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 285028 160 NIST Mass Spectrometry Data Center MS-MS #4 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 287578 69 Japan Chemical Substance Dictionary (Nikkaji) J8.590A The Japan Chemical Substance Dictionary (Nikkaji) has a search system that helps obtain knowledge from dissimilar fields and discover concepts that cross boundaries of specializations. http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J8.590A 23188374 70 KEGG C06868 KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. https://www.kegg.jp/entry/C06868 Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 31090676 71 KEGG D00252 KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. https://www.kegg.jp/entry/D00252 Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 31105000 72 Kruve Lab, Ionization & Mass Spectrometry, Stockholm University carbamazepine carbamazepine The Kruve Lab, Stockholm University is focused on revealing the ionization mechanisms, predicting ionization efficiencies and matrix effect. In other research they are addressing the site selectivity of the reactions carried out in charged nanodroplets. 20031308 75 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_2 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13616396 76 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_3 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13616397 77 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_4 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13616398 78 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_5 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13616399 79 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_6 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13616400 80 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_7 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627944 81 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_8 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627945 82 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_9 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627946 83 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_10 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627947 84 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_11 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627948 85 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_12 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627949 86 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_13 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627950 87 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_14 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627951 88 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_15 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627952 89 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_16 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627953 90 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_17 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627954 91 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_18 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627955 92 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_19 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627956 93 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_20 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13627957 94 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_21 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13665491 95 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_22 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13665492 96 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_23 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13665493 97 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_24 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13665494 98 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_25 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13665495 99 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_26 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13665496 100 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_27 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13692986 101 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_28 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13692987 102 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_29 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13698758 103 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_30 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13698759 104 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_31 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13698760 105 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_32 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13698761 106 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_33 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 13698762 107 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_34 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 15074360 108 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_35 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 15074361 109 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_36 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 15074362 110 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_37 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 15074363 111 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_38 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 15074364 112 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_39 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 20064017 113 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_40 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 20064018 114 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_41 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 31055166 115 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_42 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 31055167 116 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_43 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 31055168 117 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_44 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257037 118 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_45 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257038 119 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_46 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257039 120 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_47 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257040 121 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_48 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257041 122 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_49 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35257042 125 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_52 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35258542 126 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_53 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35258543 127 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_54 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35258544 128 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_55 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35259805 129 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_56 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35259806 130 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_57 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35259807 131 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_58 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35259808 132 MassBank Europe FFGPTBGBLSHEPO-UHFFFAOYSA-N_59 Carbamazepine MassBank Europe (MassBank.EU) was created in 2011 as an open access database of mass spectra of emerging substances to support identification of unknown substances within the NORMAN Network (https://www.norman-network.com/). MassBank.EU is the partner project of MassBank.JP, hosted at the Helmholtz Centre for Environmental Research (UFZ) Leipzig and jointly maintained by UFZ, LCSB (University of Luxembourg) and IPB Halle. https://massbank.eu/MassBank/Result.jsp?inchikey=FFGPTBGBLSHEPO-UHFFFAOYSA-N https://github.com/MassBank/MassBank-web/blob/main/MassBank-Project/LICENSE.txt 35259809 133 MassBank of North America (MoNA) WA001150 Carbamazepine MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 44 MS data records(44 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FFGPTBGBLSHEPO-UHFFFAOYSA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 24802735 134 MassBank of North America (MoNA) WA001149 Carbamazepine MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 44 MS data records(44 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FFGPTBGBLSHEPO-UHFFFAOYSA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 24802736 135 MassBank of North America (MoNA) WA001148 Carbamazepine MassBank of North America (MoNA) is a metadata-centric, auto-curating repository designed for efficient storage and querying of mass spectral records. There are total 44 MS data records(44 experimental records) for this compound, click the link above to see all spectral information at MoNA website. https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FFGPTBGBLSHEPO-UHFFFAOYSA-N%27) The content of the MoNA database is licensed under CC BY 4.0. https://mona.fiehnlab.ucdavis.edu/documentation/license 24802737 139 Metabolomics Workbench 42899 Carbamazepine The Metabolomics Workbench serves as a national and international repository for metabolomics data and metadata and provides analysis tools and access to metabolite standards, protocols, tutorials, training, and more. https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=42899 20204325 141 National Drug Code (NDC) Directory 26c3d05ebe0e24573edb51ee67b6e56a TEGRETOL The National Drug Code (NDC) is a unique, three-segment number that serves as FDA's identifier for drugs. The NDC Directory contains information on active and certified finished and unfinished drugs submitted to FDA. https://www.fda.gov/drugs/drug-approvals-and-databases/national-drug-code-directory Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 31062817 142 National Drug Code (NDC) Directory 6f55c2149fcd407327f36811c6056483 CARBAMAZEPINE The National Drug Code (NDC) is a unique, three-segment number that serves as FDA's identifier for drugs. The NDC Directory contains information on active and certified finished and unfinished drugs submitted to FDA. https://www.fda.gov/drugs/drug-approvals-and-databases/national-drug-code-directory Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 31072149 143 National Drug Code (NDC) Directory 91af0bf6a7fe1dc31096dbe9cd5be72d EPITOL The National Drug Code (NDC) is a unique, three-segment number that serves as FDA's identifier for drugs. The NDC Directory contains information on active and certified finished and unfinished drugs submitted to FDA. https://www.fda.gov/drugs/drug-approvals-and-databases/national-drug-code-directory Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 31076739 145 Nature Chemistry nchem.859-comp7 Nature Chemistry is a monthly journal dedicated to publishing high-quality papers that describe the most significant and cutting-edge research in all areas of chemistry. As well as reflecting the traditional core subjects of analytical, inorganic, organic and physical chemistry, the journal also features a broad range of chemical research including, but not limited to, catalysis, computational and theoretical chemistry, environmental chemistry, green chemistry, medicinal chemistry, nuclear chemistry, polymer chemistry, supramolecular chemistry and surface chemistry. https://pubchem.ncbi.nlm.nih.gov/substance/99343617 8517931 148 NIPH Clinical Trials Search of Japan cid2554 NIPH Clinical Trials Search of Japan allows one to search clinical research (trials) from the registries of three institutions; the University Hospital Medical Information Network Center (UMIN-CTR), the Japan Pharmaceutical Information Center (JAPIC), and the Japan Medical Association Center for Clinical Trials. https://rctportal.niph.go.jp/en/ 31187958 149 NIST Mass Spectrometry Data Center GC-MS #1 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 185235 150 NIST Mass Spectrometry Data Center GC-MS #2 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275714 151 NIST Mass Spectrometry Data Center GC-MS #3 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275718 152 NIST Mass Spectrometry Data Center GC-MS #4 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275719 153 NIST Mass Spectrometry Data Center GC-MS #5 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275723 154 NIST Mass Spectrometry Data Center GC-MS #6 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275724 155 NIST Mass Spectrometry Data Center GC-MS #7 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275725 156 NIST Mass Spectrometry Data Center GC-MS #8 for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 275726 168 SpectraBase Hm9SRztRxaB Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/Hm9SRztRxaB 4772149 169 SpectraBase KpxcONsO0mx Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/KpxcONsO0mx 4772150 161 NIST Mass Spectrometry Data Center RI for FFGPTBGBLSHEPO-UHFFFAOYSA-N Carbamazepine The NIST Mass Spectrometry Data Center, a Group in the Biomolecular Measurement Division (BMD), develops evaluated mass spectral libraries and provides related software tools. These products are intended to assist compound identification by providing reference mass spectra for GC/MS (by electron ionization) and LC-MS/MS (by tandem mass spectrometry) as well as gas phase retention indices for GC. http://www.nist.gov/srd/nist1a.cfm Data covered by the Standard Reference Data Act of 1968 as amended. https://www.nist.gov/srd/public-law 298389 162 NLM RxNorm Terminology 2002 carbamazepine RxNorm provides normalized names for clinical drugs and links its names to many of the drug vocabularies commonly used in pharmacy management and drug interaction software. https://rxnav.nlm.nih.gov/id/rxnorm/2002 The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license. https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html 15095795 192 WHO Anatomical Therapeutic Chemical (ATC) Classification N03AF01 Carbamazepine The WHO Anatomical Therapeutic Chemical (ATC) Classification System is a classification of active ingredients of drugs according to the organ or system on which they act and their therapeutic, pharmacological and chemical properties. https://www.whocc.no/atc_ddd_index/?code=N03AF01 Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed. https://www.whocc.no/copyright_disclaimer/ 24383588 164 Pharos Compound::7U7WXCCPXPYL carbamazepine Pharos gives access to a comprehensive, integrated knowledge-base for the Druggable Genome (DG) to illuminate the uncharacterized and/or poorly annotated portion of the DG, focusing on three of the most commonly drug-targeted protein families: G-protein-coupled receptors (GPCRs), Ion channels (ICs) and Kinases. It is the user interface to the Knowledge Management Center (KMC) for the Illuminating the Druggable Genome (IDG) program. https://pharos.nih.gov/ligands/7U7WXCCPXPYL Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution. https://pharos.nih.gov/about 24466941 165 Protein Data Bank in Europe (PDBe) N6W The Protein Data Bank in Europe (PDBe) manages the PDB with its wwPDB partners and provides a high-quality, up-to-date and integrated resource of macromolecular structures to support basic and applied research and education across the sciences. http://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/N6W 8763156 167 RCSB Protein Data Bank (RCSB PDB) 2554 The RCSB Protein Data Bank (PDB) contains crystallographic data defining 3D shapes of proteins, nucleic acids, and complex assemblies that helps students and researchers understand all aspects of biomedicine and agriculture, from protein synthesis to health and disease. https://www.rcsb.org/ Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data. https://www.rcsb.org/pages/policies 13145331 170 SpectraBase nvsudQ4SuY Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/nvsudQ4SuY 4772153 174 SpectraBase LECFCRnUnNo Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/LECFCRnUnNo 10098224 171 SpectraBase FbF3qV5CBf4 CARBAMAZEPINE Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/FbF3qV5CBf4 4772154 175 SpectraBase DUpOUnYt8os Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/DUpOUnYt8os 10098225 172 SpectraBase FsfunOsZ6UX Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/FsfunOsZ6UX 4772155 173 SpectraBase 9dvbiAkhs0c CARBAMAZEPINE Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/9dvbiAkhs0c 4772156 176 SpectraBase C4UFfo9EkbB Carbamazepine Wiley Science Solutions (https://sciencesolutions.wiley.com) is a leading publisher of spectral databases and KnowItAll spectroscopy software. SpectraBase provides fast text access to hundreds of thousands of NMR, IR, Raman, UV-Vis, and mass spectra. https://spectrabase.com/spectrum/C4UFfo9EkbB 13594816 178 Springer Nature 18051453-686651982 Springer Nature is the world's largest academic book publisher, publisher of the world's most influential journals, and a pioneer in the field of open research. SpringerLink provides electronic access to its book and journal content. https://pubchem.ncbi.nlm.nih.gov/substance/?source=15745&sourceid=18051453-686651982 3847030 179 SpringerMaterials smsid_bneuthoaaluflmue Dibenzo[b,f]azepine-5-carboxylic acid amide Springer Nature is the leading scientific publisher in the fields of science and related areas. The company not only publishes best-in-class scientific journals and books but is also a well-known organization compiling databases for scientific applications. Amongst these databases, SpringerMaterials helps scientist to find and use property data of materials and chemical substances. https://materials.springer.com/substanceprofile/docs/smsid_bneuthoaaluflmue 8730093 190 Thieme Chemistry 18051453-686651982 Thieme Chemistry is part of the privately owned Thieme Group and publishes highly evaluated information about synthetic and general chemistry for professional chemists and advanced students since 1909. Our portfolio includes the journals SYNFACTS, SYNLETT, SYNTHESIS and SynOpen, the synthetic methodology reference work Science of Synthesis, the German chemical encyclopedia ROEMPP, and monographs in electronic and printed format. The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license (https://creativecommons.org/licenses/by-nc-nd/4.0/), unless otherwise stated. https://pubchem.ncbi.nlm.nih.gov/substance/?source=22163&sourceid=18051453-686651982 The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated. https://creativecommons.org/licenses/by-nc-nd/4.0/ 5440585 193 WHO Model Lists of Essential Medicines 49 Carbamazepine The WHO Model Lists of Essential Medicines contains the medications considered to be most effective and safe to meet the most important needs in a health system. It has been updated every two years since 1977. https://list.essentialmeds.org/medicines/49 Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) license. https://www.who.int/about/policies/publishing/copyright 13127765 194 Wikidata Q410412 Carbamazepine Link to the compound information in Wikidata. https://www.wikidata.org/wiki/Q410412 CCZero https://creativecommons.org/publicdomain/zero/1.0/ 16291847 195 Wikipedia fm_808 carbamazepine Chemical information link to Wikipedia. https://en.wikipedia.org/wiki/Carbamazepine 24318865 196 Wikipedia c_25 Carbamazepine Link to the chemical information in Wikipedia. https://en.wikipedia.org/wiki/Carbamazepine 24321561 197 Wiley 118076 Literature references related to scientific contents from Wiley. Read more: https://onlinelibrary.wiley.com/ https://pubchem.ncbi.nlm.nih.gov/substance/?source=wiley&sourceid=118076 8298881 198 Medical Subject Headings (MeSH) 68002220 Carbamazepine MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/68002220 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 199 PubChem PubChem Data deposited in or computed by PubChem https://pubchem.ncbi.nlm.nih.gov 200 Medical Subject Headings (MeSH) DescTree MeSH Tree MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed. http://www.nlm.nih.gov/mesh/meshhome.html Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 201 ChEBI OBO ChEBI Ontology The ChEBI Ontology is a structured classification of the entities contained within ChEBI. http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology 202 KEGG br08301 Therapeutic category of drugs in Japan KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08301.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 203 KEGG br08302 USP drug classification KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08302.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 204 KEGG br08303 Anatomical Therapeutic Chemical (ATC) classification KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08303.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 205 KEGG br08310 Target-based classification of drugs KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08310.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 206 KEGG br08311 Drugs listed in the Japanese Pharmacopoeia KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08311.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 208 FDA Pharm Classes FDA_pharm_tree FDA Pharmacological Classification FDA published a final rule that amended the requirements for the content and format of approved labeling (prescribing information) for human prescription drug and biological products in January 2006. https://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling/ucm162549.htm Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 209 WHO Anatomical Therapeutic Chemical (ATC) Classification ATCTree ATC Code In the World Health Organization (WHO) Anatomical Therapeutic Chemical (ATC) classification system, the active substances are divided into different groups according to the organ or system on which they act and their therapeutic, pharmacological and chemical properties. https://www.whocc.no/atc_ddd_index/ Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed. https://www.whocc.no/copyright_disclaimer/ 210 GHS Classification (UNECE) UN_GHS_tree GHS Classification Tree The United Nations' Globally Harmonized System of Classification and Labeling of Chemicals (GHS) provides a harmonized basis for globally uniform physical, environmental, and health and safety information on hazardous chemical substances and mixtures. It sets up criteria for the classification of chemicals for physical-chemical, health, and environmental hazards of chemical substances and mixtures and sets up standardized hazard information to facilitate global trade of chemicals. Please note that obsolete codes are added in this classification for completeness purposes, as they are still in use. Any obsolete codes are annotated as such. http://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html 211 ChemIDplus ChemIDplus_tree ChemIDplus Chemical Information Classification ChemIDplus is a TOXNET (TOXicology Data NETwork) databases that contain chemicals and drugs related information. It is a product of the National Library of Medicine (NLM). https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus https://www.nlm.nih.gov/copyright.html true 212 ChEMBL Target Tree ChEMBL Protein Target Tree The ChEMBL Protein Target Tree is a structured classification of the protein target entities contained with the ChEMBL resource release version 32. https://www.ebi.ac.uk/chembl/g/#browse/targets Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/). http://www.ebi.ac.uk/Information/termsofuse.html 213 IUPHAR/BPS Guide to PHARMACOLOGY Target Classification Guide to Pharmacology Target Classification An expert-driven guide to pharmacological targets and the substances that act on them https://www.guidetopharmacology.org/targets.jsp The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/) https://www.guidetopharmacology.org/about.jsp#license 214 KEGG br08330 Drug Groups KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08330.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 215 EPA Chemical and Products Database (CPDat) cpdat_tree EPA CPDat Classification CPDat (Chemical and Products Database) is a database containing information mapping more than 49,000 chemicals to a set of terms categorizing their usage or function in 16,000 consumer products. Ref: The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125 https://www.epa.gov/chemical-research/chemical-and-products-database-cpdat https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 216 NORMAN Suspect List Exchange norman_sle_tree NORMAN Suspect List Exchange Classification The NORMAN Suspect List Exchange (NORMAN-SLE) is a central access point for NORMAN members (and others) to find suspect lists relevant for their environmental monitoring questions.<br>Update: 2024-04-30 18:00:01 https://www.norman-network.com/nds/SLE/ Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0 https://creativecommons.org/licenses/by/4.0/ 217 CCSbase ccsbase_tree CCSbase Classification CCSbase is an integrated platform consisting of a comprehensive database of Collision Cross Section (CCS) measurements taken from a variety of sources and a high-quality and high-throughput CCS prediction model trained with this database using machine learning. https://ccsbase.net/ 218 EPA DSSTox dsstoxlist_tree CompTox Chemicals Dashboard Chemical Lists This classification lists the chemical categories from the EPA CompTox Chemicals Dashboard.<br>Update: 2024-04-30 09:21:02 https://comptox.epa.gov/dashboard/chemical-lists/ https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 221 NCI Thesaurus (NCIt) NCIt NCI Thesaurus Tree The NCI Thesaurus (NCIt) provides reference terminology for many NCI and other systems. It covers vocabulary for clinical care, translational and basic research, and public information and administrative activities. https://ncit.nci.nih.gov Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. https://www.cancer.gov/policies/copyright-reuse 222 National Drug Code (NDC) Directory fdandc_tree FDA Drug Type and Pharmacologic Classification The FDA Drug Type and Pharmacologic Classification is created based on the FDA drug types and pharm classes data from the National Drug Code (NDC) Directory. https://www.fda.gov/drugs/drug-approvals-and-databases/national-drug-code-directory Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. https://www.fda.gov/about-fda/about-website/website-policies#linking 223 KEGG br08332 Drug Classes KEGG is an encyclopedia of genes and genomes. Assigning functional meanings to genes and genomes both at the molecular and higher levels is the primary objective of the KEGG database project. http://www.genome.jp/kegg-bin/get_htext?br08332.keg Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license https://www.kegg.jp/kegg/legal.html 224 EPA Substance Registry Services epasrs_tree EPA SRS List Classification Substance Registry Services (SRS) is the Environmental Protection Agency's (EPA) central system for information about substances that are tracked or regulated by EPA or other sources. It is a resource for basic information about chemicals, biological organisms, and other substances of interest to EPA and its state and tribal partners. SRS makes it possible to identify which EPA data systems, environmental statutes, or other sources have information about a substance and which synonym is used by that system or statute. https://sor.epa.gov/sor_internet/registry/substreg/LandingPage.do https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources 225 Medical Subject Headings (MeSH) 68065701 Cytochrome P-450 CYP3A Inducers MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/68065701 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 226 Medical Subject Headings (MeSH) 68018692 Antimanic Agents MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/68018692 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 227 Medical Subject Headings (MeSH) 68018712 Analgesics, Non-Narcotic MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/68018712 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 228 Medical Subject Headings (MeSH) 68026941 Sodium Channel Blockers MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/68026941 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 229 Medical Subject Headings (MeSH) 68000927 Anticonvulsants MeSH (Medical Subject Headings) is the U.S. National Library of Medicine's controlled vocabulary thesaurus used for indexing articles for PubMed. https://www.ncbi.nlm.nih.gov/mesh/68000927 Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S. https://www.nlm.nih.gov/copyright.html 230 PATENTSCOPE (WIPO) SID 403450545 The PATENTSCOPE database from WIPO includes patent and chemical structure search (with a free account) that gives access to millions of patent documents. The World Intellectual Property Organisation (WIPO) is a specialized United Nations (UN) agency headquartered in Geneva (Switzerland). Our mission is to lead the development of a balanced and effective international Intellectual Property (IP) system that enables innovation and creativity for the benefit of all. We help governments, businesses and society realize the benefits of Intellectual Property and are notably a world reference source for IP information. https://pubchem.ncbi.nlm.nih.gov/substance/403450545 231 NCBI LinkOut LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyond NCBI systems. https://www.ncbi.nlm.nih.gov/projects/linkout