CLEBOPRIDE MALATE

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

Structure Search

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)

HIDE SMILES / InChI

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
Synthesis and pharmacological properties of a series of antidopaminergic piperidyl benzamides.	1977 Mar	15078
[Clebopride, a new orthopramide with potent and selective central antidopaminergic properties].	1978 Apr	100059
[Drug-induced extrapyramidal syndrome. Apropos of 22 cases].	1987 Feb	3565961
NMDA receptor antagonists inhibit catalepsy induced by either dopamine D1 or D2 receptor antagonists.	1993 Jun 11	8359205
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	12453314
Dopamine antagonists during parturition disrupt maternal care and the retention of maternal behavior in rats.	2002 Nov	12213533
Etiological and therapeutical observations in a case of belly dancer's dyskinesia.	2006 Sep	16830316
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.	2007	21673949
Effect of clebopride, antidopaminergic gastrointestinal prokinetics, on cardiac repolarization.	2007 Jan-Feb	17365143
[Acute laryngeal dystonia due to clebopride simulating allergic reaction].	2007 Jul 7	17678608
Effectiveness and safety of levosulpiride in the treatment of dysmotility-like functional dyspepsia.	2007 Mar	18360622
Effects of vehicles and enhancers on transdermal delivery of clebopride.	2007 Sep	17958335
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
[A new method of investigation of "child's" behavior (infant-mother attachment) of newborn rats].	2010 Mar-Apr	20469600
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.

Name

Type

Language

CLEBOPRIDE MALATE

Common Name

English

CLEBOPRIDE MALATE [JAN]

Common Name

English

MOTILEX

Brand Name

English

CLEBOPRIDE HYDROGEN MALATE

Common Name

English

CLEPRID

Brand Name

English

CLEBOPRIDE MALATE [EP MONOGRAPH]

Common Name

English

CLEBOPRIDE MALATE, (±)-

Common Name

English

CLANZOL

Brand Name

English

MALIC ACID, COMPOUND WITH 4-AMINO-N-(1-(BENZYL)PIPERIDIN-4-YL)-5-CHLORO-2-METHOXYBENZAMIDE (1:1)

Common Name

English

CLEBORIL

Brand Name

English

CLEBOPRIDE MALATE [MART.]

Common Name

English

CLAST

Brand Name

English

4-AMINO-5-CHLORO-2-METHOXY-N-(1-BENZYL-4-PIPERIDYL)BENZAMIDE MALATE

Systematic Name

English

(±)-CLEBOPRIDE MALATE

Common Name

English

CLEBOPRIDE MALATE [MI]

Common Name

English

BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-(1-BENZYL-4-PIPERIDYL)-, MALATE

Systematic Name

English

AMICOS

Brand Name

English

Clebopride malate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883