CLEBOPRIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24ClN3O2
Molecular Weight	373.876
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=C(C=C(Cl)C(N)=C1)C(=O)NC2CCN(CC3=CC=CC=C3)CC2

InChI

InChIKey=BVPWJMCABCPUQY-UHFFFAOYSA-N

InChI=1S/C20H24ClN3O2/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)

HIDE SMILES / InChI

Molecular Formula	C20H24ClN3O2
Molecular Weight	373.876
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297	Antagonist 2,778		2.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting 38	Primary		Approved 8,429	CLEBOPRIDE

PubMed

Show entries

Title	Date	PubMed
Dopamine antagonists during parturition disrupt maternal care and the retention of maternal behavior in rats.	2002 Nov	12213533
[Rabbit syndrome due to clebopride].	2003 Jun 7	12812712
Review article: clinical implications of enteric and central D2 receptor blockade by antidopaminergic gastrointestinal prokinetics.	2004 Feb 15	14871277
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.	2007	21673949
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	20598654

Showing 1 to 5 of 5 entries

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Patents

Sample Use Guides

In Vivo Use Guide

500 mcg 3 times/day.

Route of Administration: Oral

In Vitro Use Guide

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.