Loperamide
- loperamide
- 53179-11-6
- Ioperamide
- Loperamida
- Loperamidum
- Create:2005-03-25
- Modify:2024-12-27
- Hydrochloride, Loperamide
- Imodium
- Loperamide
- Loperamide Hydrochloride
- Loperamide Monohydrochloride
- Monohydrochloride, Loperamide
- R 18553
- R-18553
- R18553
- loperamide
- 53179-11-6
- Ioperamide
- Loperamida
- Loperamidum
- Loperamidum [INN-Latin]
- Loperamida [INN-Spanish]
- 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
- UNII-6X9OC3H4II
- EINECS 258-416-5
- 6X9OC3H4II
- Loperamide (INN)
- BRN 1558273
- CHEBI:6532
- DTXSID6045165
- 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-N,N-dimethyl-2,2-diphenylbutanamide
- CHEMBL841
- 4-(4-Chlorophenyl)-N,N-dimethyl-alpha,alpha-diphenyl-4-hydroxy-1-piperidinebutanamide
- DTXCID4025165
- HSDB 8344
- EC 258-416-5
- 5-21-02-00379 (Beilstein Handbook Reference)
- Fortasec
- 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-
- NCGC00015608-04
- Loperacap
- LOPERAMIDE [INN]
- Apo-Loperamide
- Nu-Loperamide
- Rho-Loperamide
- Loperamidum (INN-Latin)
- Kaopectate II
- PMS-Loperamide
- Loperamida (INN-Spanish)
- Loperamide [INN:BAN]
- 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-.alpha.,.alpha.-diphenyl-
- 2-methoxyethyl1-methylethyl2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- Imodium A-D Caplets
- 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-.alpha.,.alpha.-diphenyl-1-piperidinebutyramide
- 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-N,N-dimethyl-2,2-diphenylbutanamide
- Diamide (TN)
- CAS-53179-11-6
- NSC696356
- Immodium
- Loperamid
- LoperamideHCl
- Loperamidum (Latin)
- Spectrum_000374
- Tocris-0840
- LOPERAMIDE [MI]
- LOPERAMIDE [JAN]
- Prestwick0_000144
- Prestwick1_000144
- Prestwick2_000144
- Prestwick3_000144
- Spectrum2_001738
- Spectrum3_001015
- Spectrum4_001143
- Spectrum5_001374
- Lopac-L-4762
- LOPERAMIDE [VANDF]
- LOPERAMIDE [WHO-DD]
- CBiol_001796
- Lopac0_000708
- Oprea1_109220
- SCHEMBL28530
- BSPBio_000248
- BSPBio_001381
- BSPBio_002769
- KBioGR_000101
- KBioGR_001685
- KBioSS_000101
- KBioSS_000854
- cid_71420
- DivK1c_000215
- SPBio_001816
- SPBio_002187
- BPBio1_000274
- GTPL7215
- KBio1_000215
- KBio2_000101
- KBio2_000854
- KBio2_002669
- KBio2_003422
- KBio2_005237
- KBio2_005990
- KBio3_000201
- KBio3_000202
- KBio3_001989
- NINDS_000215
- Bio1_000082
- Bio1_000571
- Bio1_001060
- Bio2_000101
- Bio2_000581
- HMS1791F03
- HMS1989F03
- HMS2089C13
- Tox21_110180
- BDBM50017698
- STK042086
- AKOS000573892
- Tox21_110180_1
- CCG-204793
- DB00836
- SDCCGSBI-0050686.P004
- 4-(4-Chlorophenyl)-N,N-dimethyl-.alpha.,.alpha.-diphenyl-4-hydroxy-1-piperidinebutanamide
- 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinebutyramide
- IDI1_000215
- IDI1_033851
- NCGC00015608-01
- NCGC00015608-02
- NCGC00015608-03
- NCGC00015608-05
- NCGC00015608-06
- NCGC00015608-07
- NCGC00015608-08
- NCGC00015608-09
- NCGC00015608-11
- NCGC00015608-15
- NCGC00015608-24
- NCGC00016828-01
- NCGC00024818-01
- NCGC00024818-02
- NCGC00024818-03
- NCGC00024818-04
- NCGC00024818-05
- DA-75076
- SBI-0050686.P003
- CAS-34552-83-5
- AB00053697
- NS00002516
- C07080
- D08144
- EN300-708764
- AB00053697-12
- AB00053697-13
- AB00053697_14
- AB00053697_15
- A829430
- L000709
- Q423751
- BRD-K61250553-001-02-9
- BRD-K61250553-003-05-8
- BRD-K61250553-003-16-5
- BRD-K61250553-003-29-8
- BRD-K61250553-003-30-6
- BRD-K61250553-003-32-2
- LOPERAMIDE OXIDE MONOHYDRATE IMPURITY A [EP IMPURITY]
- 4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-N,N-dimethyl-2,2-diphenyl-butyramide
- 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-N,N-dimethyl-2,2-diphenylbutanamide #
- 4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-N,N-dimethyl-2,2-diphenyl-butyramide(loperamide)
196.27 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
218.84 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
266.1547 100
267.1572 36.23
210.1273 22.76
238.1222 3.26
211.1301 2.72
266.1547 100
267.157 42.06
477.2299 4.11
268.1597 2.81
210.1268 2.62
477.2304 999
479.2282 312
478.2332 307
266.1532 35
266.1538 999
477.2299 843
479.2278 226
478.2331 207
267.1567 172
<b>Use (kg; approx.) in Germany (2009):</b> >250
<b>Use (kg) in USA (2002):</b> 20600
<b>Use (kg) in France (2004):</b> 318
<b>Consumption (g per capita; approx.) in Germany (2009):</b> 0.00305
<b>Consumption (g per capita) in the USA (2002):</b> 0.073
<b>Consumption (g per capita) in France (2004):</b> 0.00526
<b>Calculated removal (%):</b> 81.9
P264, P270, P301+P316, P321, P330, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
Aggregated GHS information provided per 7 reports by companies from 1 notifications to the ECHA C&L Inventory.
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.
IMAP assessments - 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-.alpha.,.alpha.-diphenyl-: Environment tier I assessment
IMAP assessments - 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-.alpha.,.alpha.-diphenyl-: Human health tier I assessment
As with most opiates in current use, therapy with loperamide has not been linked to serum enzyme elevations. There have been no convincing cases of idiosyncratic acute, clinically apparent liver injury attributed to either agent. The reason for its lack of hepatotoxicity may relate to the low doses used and lack of significant systemic absorption. What loperamide is absorbed is metabolized in the liver.
References on the safety and potential hepatotoxicity of loperamide are given in the overview section of the Opioids. Last updated: 20 May 2019
Drug Class: Gastrointestinal Agents; Opioids
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
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
◉ Summary of Use during Lactation
The amount of loperamide that enters milk from a prodrug of loperamide is minimal. Use of loperamide during breastfeeding is unlikely to affect the infant with standard doses.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=RDOIQAHITMMDAJ-UHFFFAOYSA-N
- Australian Industrial Chemicals Introduction Scheme (AICIS)1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-.alpha.,.alpha.-diphenyl-https://services.industrialchemicals.gov.au/search-assessments/
- 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/
- ChemIDplusLoperamide [INN:BAN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0053179116ChemIDplus 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_useLoperamidehttps://www.drugbank.ca/drugs/DB00836
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
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- BindingDBLICENSEAll data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).https://www.bindingdb.org/rwd/bind/info.jsp4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-N,N-dimethyl-2,2-diphenylbutanamidehttps://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50017698
- 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/downloadsLOPERAMIDEhttps://www.dgidb.org/drugs/rxcui:6468
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- Kruve Lab, Ionization & Mass Spectrometry, Stockholm Universityloperamide
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