Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H24ClN3O2.C4H6O5 |
Molecular Weight | 507.964 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CC(O)=O)C(O)=O.COC1=C(C=C(Cl)C(N)=C1)C(=O)NC2CCN(CC3=CC=CC=C3)CC2
InChI
InChIKey=NYNKCGWJPNZJMI-UHFFFAOYSA-N
InChI=1S/C20H24ClN3O2.C4H6O5/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;5-2(4(8)9)1-3(6)7/h2-6,11-12,15H,7-10,13,22H2,1H3,(H,23,25);2,5H,1H2,(H,6,7)(H,8,9)
Molecular Formula | C4H6O5 |
Molecular Weight | 134.0874 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14871277 |
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 |
|
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 |
|
[Rabbit syndrome due to clebopride]. | 2003 Jun 7 |
|
Progressive supranuclear palsy syndrome induced by clebopride. | 2004 Apr |
|
Review article: clinical implications of enteric and central D2 receptor blockade by antidopaminergic gastrointestinal prokinetics. | 2004 Feb 15 |
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Etiological and therapeutical observations in a case of belly dancer's dyskinesia. | 2006 Sep |
|
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 |
|
Acute oculogyric crisis in a patient taking clebopride. | 2008 |
|
Acute hemifacial dystonia possibly induced by clebopride. | 2009 Mar-Apr |
|
[A new method of investigation of "child's" behavior (infant-mother attachment) of newborn rats]. | 2010 Mar-Apr |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17365143
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 15:55:21 UTC 2023
by
admin
on
Fri Dec 15 15:55:21 UTC 2023
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Record UNII |
H9490V5216
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66883
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42503
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DTXSID20973227
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100000090326
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260-874-6
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SUB11828MIG
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CHEMBL325109
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57645-91-7
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H9490V5216
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C83629
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m3612
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |