Cilansetron
PubChem CID
6918107
Structure
Molecular Formula
Synonyms
- Cilansetron
- 120635-74-7
- KC-9946
- Calmactin
- 2J6DQ1U5B5
Molecular Weight
319.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2006-07-28
- Modify:2024-12-28
Description
Cilansetron is a 5HT-3 antagonist made by Solvay Pharmaceuticals that is currently under trial phase in the EU and US.
CILANSETRON is a small molecule drug with a maximum clinical trial phase of II and has 1 investigational indication.
Chemical Structure Depiction
(12R)-12-[(2-methylimidazol-1-yl)methyl]-1-azatetracyclo[7.6.1.05,16.010,15]hexadeca-5(16),6,8,10(15)-tetraen-11-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C20H21N3O/c1-13-21-9-11-22(13)12-15-7-8-17-18(20(15)24)16-6-2-4-14-5-3-10-23(17)19(14)16/h2,4,6,9,11,15H,3,5,7-8,10,12H2,1H3/t15-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
NCNFDKWULDWJDS-OAHLLOKOSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC1=NC=CN1C[C@H]2CCC3=C(C2=O)C4=CC=CC5=C4N3CCC5
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)
C20H21N3O
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 10-((2-methyl-1H-imidazol-1-yl)methyl)-5,6,8,9,10,11-hexahydro-4H-pyrido(3,2,1-jk)carbazol-11-one
- cilansetron
- Cilansetron
- 120635-74-7
- KC-9946
- Calmactin
- 2J6DQ1U5B5
- (12R)-12-[(2-methylimidazol-1-yl)methyl]-1-azatetracyclo[7.6.1.05,16.010,15]hexadeca-5(16),6,8,10(15)-tetraen-11-one
- DU-123265
- Cilansetron [INN]
- Cilansetron (USAN/INN)
- Cilansetron [USAN:INN]
- UNII-2J6DQ1U5B5
- CILANSETRON [MI]
- CILANSETRON [USAN]
- CILANSETRON [MART.]
- SCHEMBL15950
- CILANSETRON [WHO-DD]
- GTPL2297
- CHEMBL2103778
- DTXSID40152951
- BDBM50231569
- AKOS040748135
- DB04885
- HY-105109
- CS-0025026
- NS00068100
- D03495
- Q5119931
- (-)-(R)-5,6,9,10-Tetrahydro-10-((2-methylimidazol-1-yl)methyl)-4H-pyrido(3,2,1-jk)carbazol-11(8H)-one
- (10R)-5,6,9,10-TETRAHYDRO-10((2-METHYLIMIDAZOL-1-YL)METHYL)-4H-PYRIDOL(3,2,1-JK)CARBAZOL-11(8H)-ONE
- 10-((2-methyl-1H-imidazol-1-yl)methyl)-5,6,8,9,10,11-hexahydro-4H-pyrido(3,2,1-jk)carbazol-11-one
- 4H-Pyrido(3,2,1-jk)carbazol-11(8H)-one, 5,6,9,10-tetrahydro-10-((2-methyl-1H-imidazol-1-yl)methyl)-, (R)-
- 4H-PYRIDO(3,2,1-JK)CARBAZOL-11(8H)-ONE, 5,6,9,10-TETRAHYDRO-10-((2-MRTHYL-1H-INIDAZOL-1-YL)METHYL)-, (10R)-
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
319.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
319.168462302 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
319.168462302 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
39.8Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
509
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
For the treatment of symptoms associated with irritable bowel syndrome.
Cilansetron is an orally formulated medication that blocks the action of 5-hydroxy-tryptamine 3 (5-HT3) receptors. Phase III studies of cilansetron had been suspended by Solvay in order to assess whether the drug possesses safety concerns similar to alosetron. Alosetron, also a 5-HT3 antagonist, was withdrawn from the market due to questions regarding its safety. Phase III testing with cilansetron has since resumed. In June 2005 the company announced that they were reviewing the priority of the cilansetron program.
Absorption
Rapidly absorbed orally with a bioavailability of greater than 80% in rats.
The elimination half-life after 4- and 8-mg oral doses administered 3 times daily for 6 days was reported to be 1.6 to 1.9 hours.
Cilansetron is a potent and selective 5-HT3 receptor antagonist. 5-HT3 receptors are nonselective cation channels that are extensively distributed on enteric neurons in the human gastrointestinal tract, as well as other peripheral and central locations. Activation of these channels and the resulting neuronal depolarization affect the regulation of visceral pain, colonic transit and gastrointestinal secretions, processes that relate to the pathophysiology of irritable bowel syndrome (IBS). 5-HT3 receptor antagonists such as cilansetron inhibit activation of non-selective cation channels which results in the modulation of the enteric nervous system.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=NCNFDKWULDWJDS-OAHLLOKOSA-N
- CAS Common ChemistryLICENSEThe 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/
- ChemIDplusCilansetron [USAN:INN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0120635747ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useCilansetronhttps://www.drugbank.ca/drugs/DB04885
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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
- ChEMBLLICENSEAccess 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Drug Gene Interaction database (DGIdb)LICENSEThe 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/downloadsCILANSETRONhttps://www.dgidb.org/drugs/ncit:C76106
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe 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#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- Metabolomics Workbench
- NCI Thesaurus (NCIt)LICENSEUnless 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-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/CilansetronNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- PharosLICENSEData 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/aboutcilansetronhttps://pharos.nih.gov/ligands/Y4GZCUSN1ZK4
- Springer Nature
- WHO Anatomical Therapeutic Chemical (ATC) ClassificationLICENSEUse 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/
- Wikidatacilansetronhttps://www.wikidata.org/wiki/Q5119931
- WikipediaCilansetronhttps://en.wikipedia.org/wiki/Cilansetron
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmlcilansetronhttps://www.ncbi.nlm.nih.gov/mesh/67084473
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 389076617https://pubchem.ncbi.nlm.nih.gov/substance/389076617
- NCBI
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