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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] > anti-ulcer drug [CHEBI:49201]
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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