Cisapride

Structural formula
	(3 R , 4 S ) -Cisapride (top) and (3 S , 4 R ) -Cisapride (bottom), 1: 1 mixture of stereoisomers
General
Non-proprietary name	Cisapride
other names	(3 RS , 4 SR ) -4-Amino-5-chloro- N - {1- [3- (4-fluorophenoxy) propyl] -3-methoxypiperidin-4-yl} -2-methoxybenzamide ( IUPAC )
Molecular formula	C 23 H 29 ClFN 3 O 4 (cisapride) ; C 23 H 29 ClFN 3 O 4 H 2 O (cisapride monohydrate) ; C 27 H 35 ClFN 3 O 10 (cisapride tartrate ) ;
External identifiers / databases
EC number	279-689-7
ECHA InfoCard	100.072.423
PubChem	6917698
ChemSpider	5292927
DrugBank	DB00604
Wikidata	Q425295
Drug information
ATC code	A03 FA02
Mechanism of action	Serotonin (5-HT 4 ) receptor agonist
properties
Molar mass	465.95 g · mol -1 (cisapride) ; 484.0 g · mol -1 (· cisapride monohydrate) ;
Physical state	firmly
Melting point	110 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 318
	P: 280-305 + 351 + 338
Toxicological data	4166 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cisapride is a drug from the group of prokinetics , which increase motility in the upper gastrointestinal tract .

It has been withdrawn from the market in many countries because it causes irregular heartbeat ( QT syndrome ). In Germany the drug was marketed under the trade names Alimix and Propulsin until 2000 .

Chemically speaking, cisapride is a derivative of benzamide . Effectively, it is a selective serotonin agonist .

application areas

Cisapride can be used for the symptomatic treatment of heartburn in patients with reflux esophagitis , gastric paralysis , intestinal dysmotility , nausea, and constipation .

effect

Cisapride is a parasympathomimetic which a stimulation of 5-HT ₄ receptors , a release of acetylcholine causes; this leads to various effects in the upper gastrointestinal tract .

Individual evidence

^ Entry on cisapride in the DrugBank of the University of Alberta .
↑ ^a ^b ^c Data sheet Cisapride monohydrate from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
↑ Suspension of approval for cisapride from a Rote-Hand letter from the company to doctors (source: Drug Commission of the German Medical Association - www.akdae.de), accessed on February 13, 2014.

literature

CJ Estler (Ed.): Pharmacology and Toxicology . 4th edition. Schattauer, Stuttgart a. New York 1995, p. 408 .

[1] Entry on cisapride in the DrugBank of the University of Alberta .

[Sigma-2] Data sheet Cisapride monohydrate from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).

[3] Suspension of approval for cisapride from a Rote-Hand letter from the company to doctors (source: Drug Commission of the German Medical Association - www.akdae.de), accessed on February 13, 2014.