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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24ClN3O2
Molecular Weight 373.8772
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLEBOPRIDE

SMILES

COc1cc(c(cc1C(=NC2CCN(CC2)Cc3ccccc3)O)Cl)N

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
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

Targets

Primary TargetPharmacologyConditionPotency
2.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

PubMed

TitleDatePubMed
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
[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
Stereocontrolled dopamine receptor binding and subtype selectivity of clebopride analogues synthesized from aspartic acid.
2003 Oct 6
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
Etiological and therapeutical observations in a case of belly dancer's dyskinesia.
2005 Feb
Etiological and therapeutical observations in a case of belly dancer's dyskinesia.
2006 Sep
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.
2007
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
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

500 mcg 3 times/day.
Route of Administration: Oral
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
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-(1-(PHENYLMETHYL)-4-PIPERIDINYL)-
Systematic Name English
4-AMINO-5-CHLORO-2-METHOXY-N-(1-(PHENYLMETHYL)-4-PIPERIDINYL)BENZAMIDE
Systematic Name English
CLEBOPRIDE [USAN]
Common Name English
CLEBOPRIDE [MART.]
Common Name English
LAS-9273
Code English
CLEBOPRIDE [MI]
Common Name English
LAS 9273
Code English
CLEBOPRIDE [INN]
Common Name English
4-AMINO-N-(1-BENZYL-4-PIPERIDYL)-5-CHLORO-O-ANISAMIDE
Common Name English
CLEBOPRIDE [WHO-DD]
Common Name English
N-(1'-BENZYL-4'-PIPERIDYL)-2-METHOXY-4-AMINO-5-CHLOROBENZAMIDE
Common Name English
Classification Tree Code System Code
WHO-VATC QA03FA06
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
WHO-ATC A03FA06
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
NCI_THESAURUS C66883
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
259-885-9
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
EPA CompTox
55905-53-8
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
FDA UNII
I0A84520Y9
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
DRUG CENTRAL
670
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
CAS
55905-53-8
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL325109
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
RXCUI
21224
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
CLEBOPRIDE
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
NCI_THESAURUS
C83627
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
INN
3699
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
EVMPD
SUB06646MIG
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
MERCK INDEX
M3612
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB13511
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY
PUBCHEM
2780
Created by admin on Sat Jun 26 15:20:07 UTC 2021 , Edited by admin on Sat Jun 26 15:20:07 UTC 2021
PRIMARY