U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H24ClN3O2.C4H4O4
Molecular Weight 489.949
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLEBOPRIDE MALEATE

SMILES

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

InChI

InChIKey=BCVIWCRZYPHHMQ-BTJKTKAUSA-N
InChI=1S/C20H24ClN3O2.C4H4O4/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;5-3(6)1-2-4(7)8/h2-6,11-12,15H,7-10,13,22H2,1H3,(H,23,25);1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H24ClN3O2
Molecular Weight 373.876
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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

Targets

Primary TargetPharmacologyConditionPotency
2.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLEBOPRIDE
PubMed

PubMed

TitleDatePubMed
[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
Review article: clinical implications of enteric and central D2 receptor blockade by antidopaminergic gastrointestinal prokinetics.
2004 Feb 15
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.
2007
[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
Acute oculogyric crisis in a patient taking clebopride.
2008
Acute hemifacial dystonia possibly induced by clebopride.
2009 Mar-Apr
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
A randomized, controlled, double-blind trial of the adjunct use of Clebopride in polyethylene glycol electrolyte (PEG) solution for colonoscopy preparation.
2010 Jan
[A new method of investigation of "child's" behavior (infant-mother attachment) of newborn rats].
2010 Mar-Apr
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

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 Tue Oct 22 14:00:24 UTC 2019
Edited
by admin
on Tue Oct 22 14:00:24 UTC 2019
Record UNII
P42041X5SU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLEBOPRIDE MALEATE
Common Name English
4-(4-AMINO-5-CHLORO-2-METHOXYBENZAMIDO)-1-BENZYLPIPERIDINE MALEATE SALT
Common Name English
CLEBOPRIDE MALEATE SALT
Common Name English
CLEBOPRIDE HYDROGEN MALEATE
Common Name English
Code System Code Type Description
EVMPD
SUB01334MIG
Created by admin on Tue Oct 22 14:00:24 UTC 2019 , Edited by admin on Tue Oct 22 14:00:24 UTC 2019
PRIMARY
RXCUI
236701
Created by admin on Tue Oct 22 14:00:24 UTC 2019 , Edited by admin on Tue Oct 22 14:00:24 UTC 2019
PRIMARY RxNorm
PUBCHEM
6420010
Created by admin on Tue Oct 22 14:00:25 UTC 2019 , Edited by admin on Tue Oct 22 14:00:25 UTC 2019
PRIMARY
EPA CompTox
84370-95-6
Created by admin on Tue Oct 22 14:00:25 UTC 2019 , Edited by admin on Tue Oct 22 14:00:25 UTC 2019
PRIMARY
MESH
C014417
Created by admin on Tue Oct 22 14:00:24 UTC 2019 , Edited by admin on Tue Oct 22 14:00:24 UTC 2019
PRIMARY
CAS
84370-95-6
Created by admin on Tue Oct 22 14:00:24 UTC 2019 , Edited by admin on Tue Oct 22 14:00:24 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY