Cisapride

Cisapride

Clinical data
Trade names	Prepulsid, Propulsid
AHFS/Drugs.com	FDA Professional Drug Information
MedlinePlus	a694006
Pregnancy category	AU: B1
Routes of administration	oral (tablets), suspension
ATC code	A03FA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: Withdrawn
Pharmacokinetic data
Bioavailability	30-40%
Protein binding	97.5%
Metabolism	hepatic CYP3A4, intestinal
Biological half-life	10 hours
Excretion	renal, biliary
Identifiers
IUPAC name (±)-cis-4-amino-5-chloro-N-(1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl)-2-methoxybenzamide
CAS Number	81098-60-4 Y
PubChem CID	2769
IUPHAR/BPS	240
DrugBank	DB00604 Y
ChemSpider	2667 Y
UNII	UVL329170W
KEGG	D00274 Y
ChEMBL	CHEMBL1729 N
ECHA InfoCard	100.072.423
Chemical and physical data
Formula	C23H29ClFN3O4
Molar mass	465.945 g/mol
3D model (Jmol)	Interactive image
SMILES Clc1cc(c(OC)cc1N)C(=O)NC3CCN(CCCOc2ccc(F)cc2)CC3OC
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) Y Key:DCSUBABJRXZOMT-UHFFFAOYSA-N Y
NY (what is this?)

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 Pharmaceutica in 1980. In many countries, it has been either withdrawn from the market or had its indications limited because of side-effects.

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.

Cisapride has been used for the treatment of gastroesophageal reflux disease (GERD). There is no evidence it is effective for this use in children. It also increases gastric emptying in people with diabetic gastroparesis. Evidence for its use in constipation is not clear.

In many countries, it has been either withdrawn or had its indications limited because of reports of the side-effect long QT syndrome, which may cause arrhythmias. The U.S. Food and Drug Administration (FDA) issued a warning letter to doctors, and cisapride was voluntarily removed from the U.S. market on July 14, 2000. Its use in Europe has also been limited. It was banned in India and in the Philippines in 2011.