CLEBOPRIDE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24ClN3O2.ClH
Molecular Weight	410.337
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=YFLOJFUMBVJTRZ-UHFFFAOYSA-N

InChI=1S/C20H24ClN3O2.ClH/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

HIDE SMILES / InChI

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	C20H24ClN3O2
Molecular Weight	373.876
Charge	0
Count

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

Description
Sources: http://onlinelibrary.wiley.com/doi/10.1002/9781118541203.xen306/abstract

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 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14871277	Antagonist 2778		2.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14871277 https://www.drugs.com/international/clebopride.html	Primary		Approved 8429	CLEBOPRIDE Approved Use Clebopride 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
NMDA receptor antagonists inhibit catalepsy induced by either dopamine D1 or D2 receptor antagonists.	1993 Jun 11	8359205
Dopamine antagonists during parturition disrupt maternal care and the retention of maternal behavior in rats.	2002 Nov	12213533
Acute oculogyric crisis in a patient taking clebopride.	2008	18344644
Acute hemifacial dystonia possibly induced by clebopride.	2009 Mar-Apr	19512962
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
A randomized, controlled, double-blind trial of the adjunct use of Clebopride in polyethylene glycol electrolyte (PEG) solution for colonoscopy preparation.	2010 Jan	20305329
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:54:23 UTC 2023` Edited by `admin` on `Sat Dec 16 04:54:23 UTC 2023`
Record UNII	ZU312V0958
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLEBOPRIDE HYDROCHLORIDE

Common Name

English

BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-(1-(PHENYLMETHYL)-4-PIPERIDINYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

FDA UNII

ZU312V0958