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cisapride
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.


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05. Industrial Uses: pharmaceutical [CHEBI:52217] > drug [CHEBI:23888] > gastrointestinal drug [CHEBI:55324]
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more general categories    information about this item
03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 pharmacological uses [CHEBI:52210] (736) 
 neurotransmitter agent [CHEBI:35942] (471) 
 serotonergic drug [CHEBI:48278] (109) 
 serotonergic agonist [CHEBI:35941] (41) 
 cisapride [CHEBI:3720] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 anti-ulcer drug [CHEBI:49201] (25) 
 cisapride [CHEBI:3720] (1)
 gastrointestinal drug [CHEBI:55324] (24) 
 cisapride [CHEBI:3720] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 amide [CHEBI:32988] (1863) 
 primary amide [CHEBI:33256] (1586) 
 carboxamide [CHEBI:37622] (1381) 
 monocarboxylic acid amide [CHEBI:29347] (257) 
 arenecarboxamide [CHEBI:22645] (45) 
 benzamides [CHEBI:22702] (45) 
 cisapride [CHEBI:3720] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 carboxamide [CHEBI:37622] (1381) 
 monocarboxylic acid amide [CHEBI:29347] (257) 
 arenecarboxamide [CHEBI:22645] (45) 
 benzamides [CHEBI:22702] (45) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 organooxygen compound [CHEBI:36963] (11352) 
 carboxamide [CHEBI:37622] (1381) 
 monocarboxylic acid amide [CHEBI:29347] (257) 
 arenecarboxamide [CHEBI:22645] (45) 
 benzamides [CHEBI:22702] (45) 
 cisapride [CHEBI:3720] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carboxamide [CHEBI:37622] (1381) 
 monocarboxylic acid amide [CHEBI:29347] (257) 
 arenecarboxamide [CHEBI:22645] (45) 
 benzamides [CHEBI:22702] (45) 
 cisapride [CHEBI:3720] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 carboxamide [CHEBI:37622] (1381) 
 monocarboxylic acid amide [CHEBI:29347] (257) 
 arenecarboxamide [CHEBI:22645] (45) 
 benzamides [CHEBI:22702] (45) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carboxamide [CHEBI:37622] (1381) 
 monocarboxylic acid amide [CHEBI:29347] (257) 
 arenecarboxamide [CHEBI:22645] (45) 
 benzamides [CHEBI:22702] (45) 
 cisapride [CHEBI:3720] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 monocyclic compound [CHEBI:33661] (2007) 
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 piperidines [CHEBI:26151] (143) 
 cisapride [CHEBI:3720] (1)
ChEBI Compound Accession Identifier  [CHEBI:3720]
ChEBI Compound Description  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.
ChEBI Compound Identification Number  3720
ChEBI InChI Value  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
ChEBI InChIKey Value  DCSUBABJRXZOMT-IRLDBZIGSA-N
ChEBI Compound Name  cisapride
ChEBI SMILES Value  CO[C@H]1CN(CCCOc2ccc(F)cc2)CC[C@H]1NC(=O)c1cc(Cl)c(N)cc1OC
ChEBI Substance ID  93578313
ChEBI URL  ChEBI:3720
ChemSpider ID  5292927
Ontomatica Chemical Accession Key (OnChAKey)  DCSUBABJRXZOMT_IRLDBZIGSA_N_000_000000
PubChem Compound ID  6917698