Cisapride

Title: Cisapride
CAS Registry Number: 81098-60-4
CAS Name: cis-4-Amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide
Additional Names: cis-4-amino-5-chloro-N-[1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-o-anisamide
Molecular Formula: C23H29ClFN3O4
Molecular Weight: 465.95
Percent Composition: C 59.29%, H 6.27%, Cl 7.61%, F 4.08%, N 9.02%, O 13.73%
Literature References: Serotonin 5-HT4 receptor agonist. Prepn: G. Van Daele, EP 76530; idem, US 4962115 (1983, 1990 both to Janssen); and pharmacology: idem et al., Drug Dev. Res. 8, 225 (1986). Pharmacokinetics: J. A. Barone et al., Clin. Pharm. 6, 640 (1987). Review of pharmacology and therapeutic efficacy: L. R. Wiseman, D. Faulds, Drugs 47, 116-152 (1994).
Derivative Type: Monohydrate
Manufacturers' Codes: R-51619
Trademarks: Acenalin (Janssen Kyowa); Alimix (Janssen-Cilag); Cipril (Italchimici); Prepulsid (Janssen-Cilag); Propulsid (Janssen); Risamol (Yoshitomi)
Molecular Formula: C23H29ClFN3O4.H2O
Molecular Weight: 483.96
Percent Composition: C 57.08%, H 6.46%, Cl 7.33%, F 3.93%, N 8.68%, O 16.53%
Properties: Crystals from 2-propanol, mp 109.8°. Sol in acetone. Sparingly sol in methanol. Practically insol in water.
Melting point: mp 109.8°
Therap-Cat: Gastroprokinetic.
Keywords: Gastroprokinetic.
Cisplatin Citiolone Citraconic Acid Citral Citramalic Acid

Cisapride
Cisapride.svg
Cisapride 3D.png
Systematic (IUPAC) name
(±)-cis-4-amino-5-chloro-N-(1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl)-2-methoxybenzamide
Clinical data
Trade names Prepulsid, Propulsid
AHFS/Drugs.com FDA Professional Drug Information
MedlinePlus a694006
Pregnancy cat. B1 (AU)
Legal status Prescription Only (S4) (AU) POM (UK) Withdrawn (US)
Routes oral (tablets), suspension
Pharmacokinetic data
Bioavailability 30-40%
Protein binding 97.5%
Metabolism hepatic CYP3A4, intestinal
Half-life 10 hours
Excretion renal, biliary
Identifiers
CAS number 81098-60-4 YesY
ATC code A03FA02
PubChem CID 2769
IUPHAR ligand 240
DrugBank DB00604
ChemSpider 2667 YesY
UNII UVL329170W YesY
KEGG D00274 YesY
ChEMBL CHEMBL1729 N
Chemical data
Formula C23H29ClFN3O4 
Mol. mass 465.945 g/mol
 N (what is this?)  (verify)

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 U.S.). 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.[1]