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=C(OC)C=C(N)C(Cl)=C3

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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Co-administed with::
erythromycin
Sources:
healthy, newborns
n = 1
Health Status: healthy
Condition: premature infants, <36 weeks
Age Group: newborns
Sex: M+F
Population Size: 1
Sources:
Other AEs: Arrhythmia...
Other AEs:
Arrhythmia (1 patient)
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
n = 58000
Health Status: healthy
Condition: premature infants, <36 weeks
Age Group: newborns
Sex: M+F
Population Size: 58000
Sources:
Other AEs: Diarrhea...
Other AEs:
Diarrhea (12 patients)
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
n = 2
Health Status: healthy
Condition: premature infants, <36 weeks
Age Group: newborns
Sex: M+F
Population Size: 2
Sources:
Other AEs: Arrhythmia...
Other AEs:
Arrhythmia (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Co-administed with::
erythromycin
Sources:
healthy, newborns
n = 1
Health Status: healthy
Condition: premature infants, <36 weeks
Age Group: newborns
Sex: M+F
Population Size: 1
Sources:
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
n = 58000
Health Status: healthy
Condition: premature infants, <36 weeks
Age Group: newborns
Sex: M+F
Population Size: 58000
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
n = 2
Health Status: healthy
Condition: premature infants, <36 weeks
Age Group: newborns
Sex: M+F
Population Size: 2
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
Treatment of functional dyspepsia with a fixed peppermint oil and caraway oil combination preparation as compared to cisapride. A multicenter, reference-controlled double-blind equivalence study.
1999 Nov
[Lengthening of the QT-interval in a newborn treated with cisapride].
1999 Oct 16
Isolation of the serotoninergic 5-HT4(e) receptor from human heart and comparative analysis of its pharmacological profile in C6-glial and CHO cell lines.
2000 Feb
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.
2000 Feb
Fluorometric screening for metabolism-based drug--drug interactions.
2000 Jul-Aug
Efficacy and tolerability of cisapride in children.
2001
Drug interaction studies with esomeprazole, the (S)-isomer of omeprazole.
2001
[Current indications for cisapride].
2001 Apr
Cisapride decreases gastroesophageal reflux in preterm infants.
2001 Apr
The effect of cisapride on the corrected QT interval and QT dispersion in premature infants.
2001 Aug
No clinical benefit of adding cisapride to pantoprazole for treatment of gastro-oesophageal reflux disease.
2001 Aug
Survey of primary care physicians' approach to gastroesophageal reflux disease in elderly patients.
2001 Aug
[Irritable colon].
2001 Aug 20
Pharmacokinetic/pharmacodynamic assessment of the effects of E4031, cisapride, terfenadine and terodiline on monophasic action potential duration in dog.
2001 Aug-Sep
Determination of cisapride in pharmaceutical preparations using derivative spectrophotometry.
2001 Feb
Influence of coadministration of fluoxetine on cisapride pharmacokinetics and QTc intervals in healthy volunteers.
2001 Feb
[Acid-related disease in the population of two Norwegian municipalities--diagnosis and drug therapy].
2001 Feb 20
Cisapride use in preterms.
2001 Jan
Inhibition of drug metabolism in human liver microsomes by nizatidine, cimetidine and omeprazole.
2001 Jan
Possible interaction between cisapride and digoxin.
2001 Jan
Gastroesophageal reflux disease (GERD): current agents and future perspective.
2001 Jan
Gastric emptying in diabetic gastroparetic dogs: ffects of SK-951,a novel prokinetic agent.
2001 Jan
Red wine-cisapride interaction: comparison with grapefruit juice.
2001 Jul
Cisapride improves gallbladder emptying and bile lipid composition in patients with gallstones.
2001 Jul
[Gynecomastia associated with the simultaneous use of cisapride and lansoprazole].
2001 Mar 24
Contraindicated medications dispensed with cisapride: temporal trends in relation to the sending of 'Dear Doctor' letters.
2001 May
Drug safety: can simple interventions be effective in a complex world?
2001 May
Design and evaluation of a two-layer floating tablet for gastric retention using cisapride as a model drug.
2001 May
The canine Purkinje fiber: an in vitro model system for acquired long QT syndrome and drug-induced arrhythmogenesis.
2001 May
Transgenic mice overexpressing human KvLQT1 dominant-negative isoform. Part II: Pharmacological profile.
2001 May
Update on acute colonic pseudo-obstruction.
2001 Oct
Approaching disturbed sleep in late Parkinson's Disease: first step toward a proposal for a revised UPDRS.
2001 Oct
QT interval effects of cisapride in the clinical setting.
2001 Sep-Oct
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 Sat Dec 16 17:25:34 GMT 2023
Edited
by admin
on Sat Dec 16 17:25:34 GMT 2023
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
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
R-51,619
Code 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 Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
WHO-ATC A03FA02
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
NCI_THESAURUS C267
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
Code System Code Type Description
WIKIPEDIA
CISAPRIDE
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022825
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
INN
5338
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
MERCK INDEX
m3585
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY Merck Index
FDA UNII
UVL329170W
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
HSDB
3571
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
DAILYMED
UVL329170W
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
PUBCHEM
6917698
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
RXCUI
35255
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY RxNorm
SMS_ID
100000081525
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
MESH
D020117
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
CHEBI
3720
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
DRUG BANK
DB00604
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
USAN
T-87
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
279-689-7
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
RS_ITEM_NUM
1134120
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
DRUG CENTRAL
660
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
CAS
81098-60-4
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
NCI_THESAURUS
C1210
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
EVMPD
SUB07479MIG
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
LACTMED
Cisapride
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
IUPHAR
240
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL1729
Created by admin on Sat Dec 16 17:25:35 GMT 2023 , Edited by admin on Sat Dec 16 17:25:35 GMT 2023
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