CHEBI:3720 - cisapride

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ChEBI Name cisapride
ChEBI ID CHEBI:3720
Definition The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:151790, CHEBI:221485, CHEBI:143545, CHEBI:657397, CHEBI:657741
Supplier Information
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Formula C23H29ClFN3O4
Net Charge 0
Average Mass 465.94500
Monoisotopic Mass 465.183
InChI InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1
InChIKey DCSUBABJRXZOMT-IRLDBZIGSA-N
SMILES CO[C@H]1CN(CCCOc2ccc(F)cc2)CC[C@H]1NC(=O)c1cc(Cl)c(N)cc1OC
Roles Classification
Biological Role(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
Application(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
anti-ulcer drug
One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cisapride (CHEBI:3720) has role anti-ulcer drug (CHEBI:49201)
cisapride (CHEBI:3720) has role gastrointestinal drug (CHEBI:55324)
cisapride (CHEBI:3720) has role serotonergic agonist (CHEBI:35941)
cisapride (CHEBI:3720) is a aromatic ether (CHEBI:35618)
cisapride (CHEBI:3720) is a benzamides (CHEBI:22702)
cisapride (CHEBI:3720) is a monochlorobenzenes (CHEBI:83403)
cisapride (CHEBI:3720) is a organofluorine compound (CHEBI:37143)
cisapride (CHEBI:3720) is a piperidines (CHEBI:26151)
cisapride (CHEBI:3720) is a substituted aniline (CHEBI:48975)
IUPAC Name
4-amino-5-chloro-N-{cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl}-2-methoxybenzamide
INNs Sources
cisaprida ChemIDplus
cisapride ChemIDplus
cisapridum ChemIDplus
Synonyms Sources
(±)-cisapride ChemIDplus
4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide ChEMBL
4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide ChEMBL
cis-4-amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide ChemIDplus
cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide ChEBI
cis-4-amino-5-chloro-N-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-o-anisamide ChEBI
Cisapride KEGG COMPOUND
Database Links Databases
C06910 KEGG COMPOUND
D00274 KEGG DRUG
DB00604 DrugBank
EP76530 Patent
LSM-2133 LINCS
US4962115 Patent
View more database links
Registry Numbers Types Sources
81098-60-4 CAS Registry Number KEGG COMPOUND
81098-60-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10891117 PubMed citation ChEMBL
12190308 PubMed citation ChEMBL
19110341 PubMed citation ChEMBL
19663444 PubMed citation ChEMBL
1995885 PubMed citation ChEMBL
2139471 PubMed citation ChEMBL
Last Modified
24 February 2016