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=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
| 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 Date1993 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| 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 Sources: |
healthy, newborns |
Other AEs: Diarrhea... |
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 |
Other AEs: Arrhythmia... |
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 |
Other AEs: Arrhythmia... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
| 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 |
| 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 |
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 |
|---|---|---|
| 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
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
Wed Apr 02 09:06:15 GMT 2025
by
admin
on
Wed Apr 02 09:06:15 GMT 2025
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| Record UNII |
UVL329170W
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Validated (UNII)
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WHO-VATC |
QA03FA02
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CFR |
21 CFR 216.24
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WHO-ATC |
A03FA02
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C267
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CISAPRIDE
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m3585
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UVL329170W
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3571
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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 |
|---|---|---|---|---|---|---|
| Biological Half-life | PHARMACOKINETIC |
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