Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H24ClN3O2.ClH.H2O |
| Molecular Weight | 428.353 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.COC1=C(C=C(Cl)C(N)=C1)C(=O)NC2CCN(CC3=CC=CC=C3)CC2
InChI
InChIKey=NTUDMRPSPGYWMY-UHFFFAOYSA-N
InChI=1S/C20H24ClN3O2.ClH.H2O/c1-26-19-12-18(22)17(21)11-16(19)20(25)23-15-7-9-24(10-8-15)13-14-5-3-2-4-6-14;;/h2-6,11-12,15H,7-10,13,22H2,1H3,(H,23,25);1H;1H2
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C20H24ClN3O2 |
| Molecular Weight | 373.876 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Clebopride is a dopamine antagonist drug. It is used to treat functional gastrointestinal disorder such as nausea or vomiting. Unchanged parent drug was the most abundant compound in human urine. Major metabolites included the hydroxylation at benzyl group to yield carbinolamine and its further N-dealkylation product, and the piperidine ring hydroxylation/oxidation metabolite (a lactam).
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL217 |
2.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CLEBOPRIDE Approved UseClebopride is used in the treatment of stomach ulcer, inflammation of stomach and intestine, indigestion. It also reduces the symptoms like excessive air accumulation in gut, nausea and vomiting associated with stomach discomfort. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and pharmacological properties of a series of antidopaminergic piperidyl benzamides. | 1977 Mar |
|
| [Clebopride, a new orthopramide with potent and selective central antidopaminergic properties]. | 1978 Apr |
|
| [Drug-induced extrapyramidal syndrome. Apropos of 22 cases]. | 1987 Feb |
|
| NMDA receptor antagonists inhibit catalepsy induced by either dopamine D1 or D2 receptor antagonists. | 1993 Jun 11 |
|
| Angiogenic and angiostatic factors in systemic sclerosis: increased levels of vascular endothelial growth factor are a feature of the earliest disease stages and are associated with the absence of fingertip ulcers. | 2002 |
|
| Dopamine antagonists during parturition disrupt maternal care and the retention of maternal behavior in rats. | 2002 Nov |
|
| [Rabbit syndrome due to clebopride]. | 2003 Jun 7 |
|
| Progressive supranuclear palsy syndrome induced by clebopride. | 2004 Apr |
|
| Etiological and therapeutical observations in a case of belly dancer's dyskinesia. | 2005 Feb |
|
| Etiological and therapeutical observations in a case of belly dancer's dyskinesia. | 2006 Sep |
|
| Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials. | 2007 |
|
| Effect of clebopride, antidopaminergic gastrointestinal prokinetics, on cardiac repolarization. | 2007 Jan-Feb |
|
| [Acute laryngeal dystonia due to clebopride simulating allergic reaction]. | 2007 Jul 7 |
|
| Effectiveness and safety of levosulpiride in the treatment of dysmotility-like functional dyspepsia. | 2007 Mar |
|
| Effects of vehicles and enhancers on transdermal delivery of clebopride. | 2007 Sep |
|
| Development and validation of a LC-MS/MS method for the determination of clebopride and its application to a pharmacokinetics study in healthy Chinese volunteers. | 2010 Aug 1 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
Clebopride at 10 uM significantly decreased the Vmax of phase 0 depolarization in isolated rabbit Purkinje fiber and significantly prolonged the action potential duration at 90% repolarization, whereas the action potential duration at 50% repolarization was not prolonged. For hERG potassium channel currents in human ether-à-go-go-related gene (hERG)-stably transfected Chinese hamster ovarian (CHO) cells the IC50 value was 0.62 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:09:00 UTC 2023
by
admin
on
Fri Dec 15 16:09:00 UTC 2023
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| Record UNII |
Y01345MLEW
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C66883
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C83628
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21152066
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m3612
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Y01345MLEW
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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|---|---|---|---|---|
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ACTIVE MOIETY |