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
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
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 |
DescriptionSources: http://www.rxlist.com/propulsid-drug.htmCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/propulsid.html | http://www.marvistavet.com/cisapride.pml
Sources: http://www.rxlist.com/propulsid-drug.htm
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.
CNS Activity
Originator
Sources: https://www.google.com/patents/US4962115
Curator's Comment: # Janssen Pharmaceutica N.V.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1875 Sources: http://www.rxlist.com/propulsid-drug.htm |
41.5 nM [Ki] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10780971 |
|||
Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10780971 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | PROPULSID Approved UseCisapride is indicated for the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease. Launch Date7.4390399E11 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... |
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... |
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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Ki 14 uM] | ||||
yes [Ki 16.1 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | yes (co-administration study) Comment: Ketoconazole resulted in an 8 fold increase and fluconazole more than doubled the AUC of cisapride. Many other DDIs: see https://pubmed.ncbi.nlm.nih.gov/10926350/ Page: 10.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Does cisapride influence cardiac rhythm? Results of a United States multicenter, double-blind, placebo-controlled pediatric study. | 2001 Apr |
|
Synergistic and antagonistic pharmacodynamic interaction between ranitidine and cisapride: a study on the isolated rabbit intestine. | 2001 Apr |
|
Electrogastrography: a non-invasive measurement of gastric function. | 2001 Apr-Jun |
|
The effect of cisapride on the corrected QT interval and QT dispersion in premature infants. | 2001 Aug |
|
Effects of 5-HT(4) receptor agonists, cisapride and mosapride citrate on electrocardiogram in anaesthetized rats and guinea-pigs and conscious cats. | 2001 Aug |
|
Gastrointestinal tract cytomegalovirus infection with prolonged vomiting and fever in an immunocompetent child. | 2001 Aug |
|
Enteral feeding in the critically ill: comparison between the supine and prone positions: a prospective crossover study in mechanically ventilated patients. | 2001 Aug |
|
A randomised controlled trial of four management strategies for dyspepsia: relationships between symptom subgroups and strategy outcome. | 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 |
|
Cisapride does not improve precolonoscopy bowel preparation with either sodium phosphate or polyethylene glycol electrolyte lavage. | 2001 Aug |
|
Stereoselective metabolism of cisapride and enantiomer-enantiomer interaction in human cytochrome P450 enzymes: major role of CYP3A. | 2001 Aug |
|
[Irritable colon]. | 2001 Aug 20 |
|
Cisapride and the Vanessa Young inquest. | 2001 Aug 21 |
|
Pharmacokinetic/pharmacodynamic assessment of the effects of E4031, cisapride, terfenadine and terodiline on monophasic action potential duration in dog. | 2001 Aug-Sep |
|
Cisapride use in preterms. | 2001 Jan |
|
[Anorexia nervosa or somatic disease]. | 2001 Jul |
|
A randomized, double-blind placebo-controlled trial of the effects of the 5-hydroxytriptamine(4) agonist cisapride on the female urinary bladder. | 2001 Jul |
|
Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man. | 2001 Jul |
|
Cisapride plasma levels and corrected QT interval in infants undergoing routine polysomnography. | 2001 Jul |
|
Effects of cisapride on ventricular depolarization-repolarization and arrhythmia markers in infants. | 2001 Jul |
|
Red wine-cisapride interaction: comparison with grapefruit juice. | 2001 Jul |
|
Cisapride improves gallbladder emptying and bile lipid composition in patients with gallstones. | 2001 Jul |
|
Pharmacological characterization of a novel 5-HT4 receptor agonist, TS-951, in vitro. | 2001 Jul |
|
Pneumatosis intestinalis in a patient with polymyositis. | 2001 Jul-Aug |
|
Study of the drug-drug interaction between simvastatin and cisapride in man. | 2001 Jun |
|
Postmarketing reports of QT prolongation and ventricular arrhythmia in association with cisapride and Food and Drug Administration regulatory actions. | 2001 Jun |
|
Cisapride associated with QTc prolongation in very low birth weight preterm infants. | 2001 Jun |
|
"Use-dependent" effects of cisapride on postrest action potentials in rabbit ventricular myocardium. | 2001 Jun 22 |
|
Effect of cisapride on gastric sensitivity to distension, gastric compliance and duodeno-gastric reflexes in healthy humans. | 2001 Jun-Jul |
|
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 |
|
Mechanisms of cisapride affecting gallbladder motility. | 2001 May |
|
Cisapride and patient information leaflets. | 2001 May 1 |
|
Canada needs better drug reporting, says inquest. | 2001 May 5 |
|
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 |
|
The role of age and salivation in acid clearance in symptomatic patients with gastro-oesophageal reflux disease. | 2001 Sep |
|
Dyspepsia in primary care: acid suppression as effective as prokinetic therapy. A randomized clinical trial. | 2001 Sep |
|
Treatment of non-ulcer dyspepsia: a meta-analysis of placebo-controlled prospective studies. | 2001 Sep |
|
[Drug therapy of functional dyspepsia. A review based on Cochrane Reviews]. | 2001 Sep 10 |
|
QT interval effects of cisapride in the clinical setting. | 2001 Sep-Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/propulsid.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6143806
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
Edited
Sat Dec 16 17:25:34 UTC 2023
by
admin
on
Sat Dec 16 17:25:34 UTC 2023
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Record UNII |
UVL329170W
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QA03FA02
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WHO-ATC |
A03FA02
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NCI_THESAURUS |
C267
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CISAPRIDE
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DTXSID3022825
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5338
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m3585
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UVL329170W
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3571
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6917698
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35255
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100000081525
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D020117
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DB00604
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T-87
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279-689-7
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1134120
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81098-60-4
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C1210
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SUB07479MIG
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Cisapride
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240
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CHEMBL1729
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS | |||
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TARGET -> AGONIST | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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