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CHEBI:3720 - cisapride

ChEBI IDCHEBI:3720
ChEBI Namecisapride
Stars
DefinitionThe 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.
Secondary ChEBI IDsCHEBI:143545, CHEBI:151790, CHEBI:221485, CHEBI:657397, CHEBI:657741
Last Modified24 February 2016
DownloadsMolfile
FormulaC23H29ClFN3O4
Net Charge0
Average Mass465.953
Monoisotopic Mass465.18306
SMILESCOc1cc(N)c(Cl)cc1C(=O)N[C@@H]1CCN(CCCOc2ccc(F)cc2)C[C@@H]1OC
InChIInChI=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
InChIKeyDCSUBABJRXZOMT-IRLDBZIGSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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.
Applications:
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.
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
cisapridumChemIDplus
cisaprideChemIDplus
cisapridaChemIDplus
Synonyms  Source
CisaprideKEGG COMPOUND
4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamideChEMBL
4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamideChEMBL
(±)-cisaprideChemIDplus
cis-4-amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamideChemIDplus
cis-4-amino-5-chloro-N-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-o-anisamideChEBI
Manual XrefsDatabases
C06910KEGG COMPOUND
DB00604DrugBank
D00274KEGG DRUG
EP76530Patent
US4962115Patent
LSM-2133LINCS
Registry NumbersSources
CAS:81098-60-4KEGG COMPOUND
CAS:81098-60-4ChemIDplus
Citations