cisapride

Trade name: Propulsid

Small moleculeapproved

Approved

Jul 29, 1993

Cisapride is chemically related to metoclopramide, but unlike metoclopramide, it does not cross the blood-brain barrier or have antidopaminergic effects. Cisapride is a serotonin-4 (5-HT4) receptor agonist. Cisapride was indicated for the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease. The Food and Drug Administration (FDA) in America stopped the marketing of cisapride as of 14th July 2000. They had received at least 341 reports of heart rhythm abnormalities and these led to 80 deaths. Other reported adverse effects are: headache, diarrhea, abdominal pain, nausea, constipation. Cisapride for animals has been found helpful in some cases of megaesophagus and is a common treatment for feline megacolon. Clarithromycin, erythromycin, and troleandomycin markedly inhibit the metabolism of cisapride. Concurrent administration of certain anticholinergic compounds, such as belladonna alkaloids and dicyclomine, would be expected to compromise the beneficial effects of cisapride. — NCATS

Clinical trial activity

4 trials · 1 clinical orgs · 1 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Mar 1, 2003 (NCT01281566)

Timeline

1990s

Jul 29, 1993
Johnson and Johnson — Earliest FDA Approval
Jul 29, 1993
Johnson and Johnson — NDA Organization
Nov 7, 1997
Johnson and Johnson — NDA Secondary Org

Indications

Approved for

Heartburn (approved 1993)

Studied for

Mechanism of action

Serotonin 4 (5-HT4) receptorAGONIST
HTR4 agonist
- 5-hydroxytryptamine receptor 4 (HTR4) ↗

Approval history

approvedJul 29, 1993

Chemistry & pharmacology

Loading structure…

SMILES

COc1cc(N)c(Cl)cc1C(=O)NC1CCN(CCCOc2ccc(F)cc2)CC1OC

Mol. weight: 465.95 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Racemic Mixture
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Discontinued

Oral

Yes

Parenteral

Topical

Sources

Also known as

4-amino-5-chloro-n-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide
4-amino-5-chloro-n-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide
4-amino-5-chloro-n-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide
4-amino-5-chloro-n-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide
acenalin
alimix
alimix
alimix
cipril
cis-4-amino-5-chloro-n-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide
cis-4-amino-5-chloro-n-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide
cis-4-amino-5-chloro-n-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-o-anisamide
cis-4-amino-5-chloro-n-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-o-anisamide
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-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide
cisaprid
cisaprid
cisaprida
cisaprida
cisapride
cisapride
cisapride
cisapride
cisapride
cisapride
cisapride
cisapride
cisapride
cisapride
cisapride
(+-)-cisapride
(+-)-cisapride
cisapride monohydrate
cisapride monohydrate
cisapride monohydrate
cisapride monohydrate
cisapridum
cisapridum
coordinax
prepulsid
prepulsid
prepulsid
prepulsid quicklet
propulsid
propulsid
propulsid
propulsid
propulsid quicksolv
propulsid quicksolv
r51619
r51619
r51619
r51619
r51619
r51619
r 51619
r-51619
r-51619
r-51619
risamal

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT01281553	Phase 4	Sep 1, 2003	Johnson and Johnson
NCT01286090	Phase 4	Jul 1, 2003	Johnson and Johnson
NCT01281540	Phase 4	May 1, 2003	Johnson and Johnson
NCT01281566	Phase 4	Mar 1, 2003	Johnson and Johnson

Showing 4 of 4 trials

Page 1 / 1

Organizations

Research & Development (1)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Johnson and Johnson	For profit	4	4	1	2003

1 organizations

Page 1 / 1

Marketing (3)

Organization	Org type	Relationship	Date
Johnson and Johnson	For profit	NDA2	Nov 7, 1997
Johnson and Johnson	For profit	SYN	Jul 29, 1993
Johnson and Johnson	For profit	NDA	Jul 29, 1993