U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H29ClFN3O4
Molecular Weight 465.945
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CISAPRIDE

SMILES

CO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C3=CC(Cl)=C(N)C=C3OC

InChI

InChIKey=DCSUBABJRXZOMT-IRLDBZIGSA-N
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)/t20-,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula C23H29ClFN3O4
Molecular Weight 465.945
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/propulsid.html | http://www.marvistavet.com/cisapride.pml

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.

Originator

Curator's Comment: # Janssen Pharmaceutica N.V.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
41.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PROPULSID

Approved Use

Cisapride is indicated for the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.

Launch Date

1993
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.5 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.5 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORCISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
75.7 ng/mL
10 mg 4 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
115.1 ng/mL
20 mg 4 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
190.4 ng/mL
40 mg 4 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
719 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
88.1 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORCISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1193 ng × h/mL
10 mg 4 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1925 ng × h/mL
20 mg 4 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2978 ng × h/mL
40 mg 4 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.7 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
8.2 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORCISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.77 h
10 mg 4 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.98 h
20 mg 4 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
9.76 h
40 mg 4 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CISAPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.2 mg/kg 4 times / day steady, oral
Recommended
Dose: 0.2 mg/kg, 4 times / day
Route: oral
Route: steady
Dose: 0.2 mg/kg, 4 times / day
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sex: M+F
Sources:
Other AEs: Diarrhea...
Other AEs:
Diarrhea (12 patients)
Sources:
0.2 mg/kg 4 times / day steady, oral
Recommended
Dose: 0.2 mg/kg, 4 times / day
Route: oral
Route: steady
Dose: 0.2 mg/kg, 4 times / day
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sex: M+F
Sources:
Other AEs: Arrhythmia...
Other AEs:
Arrhythmia (1 patient)
Sources:
2 mg/kg 4 times / day steady, oral
Studied dose
Dose: 2 mg/kg, 4 times / day
Route: oral
Route: steady
Dose: 2 mg/kg, 4 times / day
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sex: M+F
Sources:
Other AEs: Arrhythmia...
Other AEs:
Arrhythmia (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 12 patients
0.2 mg/kg 4 times / day steady, oral
Recommended
Dose: 0.2 mg/kg, 4 times / day
Route: oral
Route: steady
Dose: 0.2 mg/kg, 4 times / day
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sex: M+F
Sources:
Arrhythmia 1 patient
0.2 mg/kg 4 times / day steady, oral
Recommended
Dose: 0.2 mg/kg, 4 times / day
Route: oral
Route: steady
Dose: 0.2 mg/kg, 4 times / day
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sex: M+F
Sources:
Arrhythmia 2 patients
2 mg/kg 4 times / day steady, oral
Studied dose
Dose: 2 mg/kg, 4 times / day
Route: oral
Route: steady
Dose: 2 mg/kg, 4 times / day
Sources:
healthy, newborns
Health Status: healthy
Age Group: newborns
Sex: M+F
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 14 uM]
yes [Ki 16.1 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
QT interval effects of cisapride in the clinical setting.
2001-10-02
Update on acute colonic pseudo-obstruction.
2001-10
Approaching disturbed sleep in late Parkinson's Disease: first step toward a proposal for a revised UPDRS.
2001-10
Pharmacokinetic/pharmacodynamic assessment of the effects of E4031, cisapride, terfenadine and terodiline on monophasic action potential duration in dog.
2001-09-25
[Drug therapy of functional dyspepsia. A review based on Cochrane Reviews].
2001-09-10
Effect of cisapride on gastric sensitivity to distension, gastric compliance and duodeno-gastric reflexes in healthy humans.
2001-09-01
The role of age and salivation in acid clearance in symptomatic patients with gastro-oesophageal reflux disease.
2001-09
Dyspepsia in primary care: acid suppression as effective as prokinetic therapy. A randomized clinical trial.
2001-09
Treatment of non-ulcer dyspepsia: a meta-analysis of placebo-controlled prospective studies.
2001-09
Cisapride and the Vanessa Young inquest.
2001-08-21
[Irritable colon].
2001-08-20
Pneumatosis intestinalis in a patient with polymyositis.
2001-08-09
Electrogastrography: a non-invasive measurement of gastric function.
2001-08-09
The effect of cisapride on the corrected QT interval and QT dispersion in premature infants.
2001-08
Effects of 5-HT(4) receptor agonists, cisapride and mosapride citrate on electrocardiogram in anaesthetized rats and guinea-pigs and conscious cats.
2001-08
Gastrointestinal tract cytomegalovirus infection with prolonged vomiting and fever in an immunocompetent child.
2001-08
Enteral feeding in the critically ill: comparison between the supine and prone positions: a prospective crossover study in mechanically ventilated patients.
2001-08
A randomised controlled trial of four management strategies for dyspepsia: relationships between symptom subgroups and strategy outcome.
2001-08
No clinical benefit of adding cisapride to pantoprazole for treatment of gastro-oesophageal reflux disease.
2001-08
Survey of primary care physicians' approach to gastroesophageal reflux disease in elderly patients.
2001-08
Cisapride does not improve precolonoscopy bowel preparation with either sodium phosphate or polyethylene glycol electrolyte lavage.
2001-08
Stereoselective metabolism of cisapride and enantiomer-enantiomer interaction in human cytochrome P450 enzymes: major role of CYP3A.
2001-08
[Anorexia nervosa or somatic disease].
2001-07
A randomized, double-blind placebo-controlled trial of the effects of the 5-hydroxytriptamine(4) agonist cisapride on the female urinary bladder.
2001-07
Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man.
2001-07
Cisapride plasma levels and corrected QT interval in infants undergoing routine polysomnography.
2001-07
Effects of cisapride on ventricular depolarization-repolarization and arrhythmia markers in infants.
2001-07
Red wine-cisapride interaction: comparison with grapefruit juice.
2001-07
Cisapride improves gallbladder emptying and bile lipid composition in patients with gallstones.
2001-07
Pharmacological characterization of a novel 5-HT4 receptor agonist, TS-951, in vitro.
2001-07
"Use-dependent" effects of cisapride on postrest action potentials in rabbit ventricular myocardium.
2001-06-22
Study of the drug-drug interaction between simvastatin and cisapride in man.
2001-06
Postmarketing reports of QT prolongation and ventricular arrhythmia in association with cisapride and Food and Drug Administration regulatory actions.
2001-06
Gastric emptying in the critically ill.
2001-06
Cisapride associated with QTc prolongation in very low birth weight preterm infants.
2001-06
Canada needs better drug reporting, says inquest.
2001-05-05
Contraindicated medications dispensed with cisapride: temporal trends in relation to the sending of 'Dear Doctor' letters.
2001-05
Drug safety: can simple interventions be effective in a complex world?
2001-05
Design and evaluation of a two-layer floating tablet for gastric retention using cisapride as a model drug.
2001-05
Mechanisms of cisapride affecting gallbladder motility.
2001-05
Does cisapride influence cardiac rhythm? Results of a United States multicenter, double-blind, placebo-controlled pediatric study.
2001-04
Synergistic and antagonistic pharmacodynamic interaction between ranitidine and cisapride: a study on the isolated rabbit intestine.
2001-04
Cisapride use in preterms.
2001-01
Efficacy and tolerability of cisapride in children.
2001
Comparative safety of the different macrolides.
2001
Drug interaction studies with esomeprazole, the (S)-isomer of omeprazole.
2001
Gastroesophageal reflux in infants and children.
2001
Evaluation of drug-induced QT interval prolongation: implications for drug approval and labelling.
2001
Saquinavir soft gelatin capsule: a comparative safety review.
2001
[The effect of prokinetic treatment and eradication of Helicobacter pylori on gastric emptying and symptoms of functional dyspepsia].
2001
Patents

Sample Use Guides

Initiate therapy with one 10 mg tablet or 10 mL of the suspension 4 times daily at least 15 minutes before meals and at bedtime. In some patients the dosage will need to be increased to 20 mg, given as above, to obtain a satisfactory result.
Route of Administration: Oral
In Vitro Use Guide
The addition of Cisapride to the mucosal solution to give a concentration of 6 x 10-5 M caused a transient rise in potential difference (PD, P < 0.05) and short-circuit current (SCC, P < 0.05) with no significant (P > 0.05) change in tissue resistance.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:06:15 GMT 2025
Edited
by admin
on Wed Apr 02 09:06:15 GMT 2025
Record UNII
UVL329170W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CISAPRIDE
HSDB   INN   JAN   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
R-51,619
Preferred Name English
CISAPRIDE [HSDB]
Common Name English
CISAPRIDE [MI]
Common Name English
CISAPRIDE [JAN]
Common Name English
R-51619
Code English
CISAPRIDE [USAN]
Common Name English
CIS-4-AMINO-5-CHLORO-N-(1-(3-(P-FLUOROPHENOXY)PROPYL)-3-METHOXY-4-PIPERIDYL)-O-ANISAMIDE
Common Name English
cisapride [INN]
Common Name English
CISAPRIDE [USP-RS]
Common Name English
Cisapride [WHO-DD]
Common Name English
CISAPRIDE [VANDF]
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-N-(1-(3-(4-FLUOROPHENOXY)PROPYL)-3-METHOXY-4-PIPERIDINYL)-2-METHOXY-, CIS
Common Name English
CISAPRIDE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
WHO-VATC QA03FA02
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
CFR 21 CFR 216.24
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
WHO-ATC A03FA02
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
NCI_THESAURUS C267
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
Code System Code Type Description
WIKIPEDIA
CISAPRIDE
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID3022825
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
INN
5338
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
MERCK INDEX
m3585
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY Merck Index
FDA UNII
UVL329170W
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
HSDB
3571
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
DAILYMED
UVL329170W
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
PUBCHEM
6917698
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
RXCUI
35255
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY RxNorm
SMS_ID
100000081525
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
MESH
D020117
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
CHEBI
3720
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
DRUG BANK
DB00604
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
USAN
T-87
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
279-689-7
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1134120
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
DRUG CENTRAL
660
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
CAS
81098-60-4
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
NCI_THESAURUS
C1210
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
EVMPD
SUB07479MIG
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
LACTMED
Cisapride
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
IUPHAR
240
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL1729
Created by admin on Wed Apr 02 09:06:15 GMT 2025 , Edited by admin on Wed Apr 02 09:06:15 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
TARGET -> AGONIST
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC