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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 of CLEBOPRIDE MALATE

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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 2.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

PubMed

TitleDatePubMed
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
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
[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

US4978531A
5

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
EP   JAN   MART.   MI   WHO-DD  
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
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
Code System Code Type Description
PUBCHEM
42503
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID20973227
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
SMS_ID
100000090326
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
260-874-6
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
EVMPD
SUB11828MIG
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL325109
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
CAS
57645-91-7
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
FDA UNII
H9490V5216
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
NCI_THESAURUS
C83629
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY
MERCK INDEX
m3612
Created by admin on Fri Dec 15 15:55:21 GMT 2023 , Edited by admin on Fri Dec 15 15:55:21 GMT 2023
PRIMARY Merck Index
ACTIVE MOIETY
Structure of CLEBOPRIDE
PARENT (SALT/SOLVATE)
Structure of Malic acid
SUBSTANCE RECORD
Structure of CLEBOPRIDE MALATE
NIH
NCATS
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