Structure via PubChem · Public domain (PubChem)
cisapride
Sign in to saveAlso known as 4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide, cis-4-amino-5-chloro-N-(1-(3-(P-Fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-O-anisamide, cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide, (+-)-Cisapride, cis-4-amino-5-chloro-N-{1-[3-(P-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-O-anisamide, 4-amino-5-chloro-N-(1-(3-(4-Fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide, (+)-(R)-Cisapride, Cisaprid
Cisapride is a gastroprokinetic agent, a drug that increases motility in the upper gastrointestinal tract. It acts directly as a serotonin 5-HT4 receptor agonist and indirectly as a parasympathomimetic. Stimulation of the serotonin receptors increases acetylcholine release in the enteric nervous system. It has been sold under the trade names Prepulsid (Janssen-Ortho) and Propulsid (in the United States). It was discovered by Janssen Pharmaceuticals in 1980. In many countries, it has been either withdrawn from the market or had its indications limited due to incidence of serious cardiac side-ef
Chemical data
- Formula
- C23H29ClFN3O4
- Molecular weight
- 465.9 g/mol
- IUPAC name
- 4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
- SMILES
- CO[C@H]1CN(CC[C@H]1NC(=O)C2=CC(=C(C=C2OC)N)Cl)CCCOC3=CC=C(C=C3)F
- InChIKey
- DCSUBABJRXZOMT-IRLDBZIGSA-N
- XLogP
- 3.4
- Polar surface area
- 86.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
2,083 papers- Cisapride poisoning.Veterinary and human toxicology · 1997
- Cisapride for gastric emptying in diabetic patients: a meta-analysis on its efficacy and safety.Hormones (Athens, Greece) · 2025
- Cisapride for intestinal constipation.The Cochrane database of systematic reviews · 2011
- Cisapride. Drug interactions of clinical significance.Drug safety · 1996
- Cisapride and anaesthesia.British journal of anaesthesia · 1989
via PubMed
Wikidata facts
- Mass
- 465.183062
Show 6 more facts
- chemical formula
- C₂₃H₂₉ClFN₃O₄
- Commons category
- Cisapride
- World Health Organisation international non-proprietary name
- cisapride
- isomeric SMILES
- CO[C@H]1CN(CC[C@H]1NC(=O)C2=CC(=C(C=C2OC)N)Cl)CCCOC3=CC=C(C=C3)F
- canonical SMILES
- COC1CN(CCC1NC(=O)C2=CC(=C(C=C2OC)N)Cl)CCCOC3=CC=C(C=C3)F
- defined daily dose
- 30
via Wikidata · CC0
~3 min read
Article
8 sectionsContents
- Medical uses
- Veterinary uses
- Kinetics
- Pharmacology and mechanism of action
- See also
- References
- Further reading
- External links
Cisapride is a gastroprokinetic agent, a drug that increases motility in the upper gastrointestinal tract. It acts directly as a serotonin 5-HT4 receptor agonist and indirectly as a parasympathomimetic. Stimulation of the serotonin receptors increases acetylcholine release in the enteric nervous system. It has been sold under the trade names Prepulsid (Janssen-Ortho) and Propulsid (in the United States). It was discovered by Janssen Pharmaceuticals in 1980. In many countries, it has been either withdrawn from the market or had its indications limited due to incidence of serious cardiac side-effects. Propulsid was linked to children's deaths.
The commercial preparations of this drug are the racemic mixture of both enantiomers of the compound. The (+) enantiomer itself has the major pharmacologic effects and does not induce many of the detrimental side-effects of the mixture.