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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

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

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
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
[Rabbit syndrome due to clebopride].
2003 Jun 7
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.
2006 Sep
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
Acute oculogyric crisis in a patient taking clebopride.
2008
Acute hemifacial dystonia possibly induced by clebopride.
2009 Mar-Apr
[A new method of investigation of "child's" behavior (infant-mother attachment) of newborn rats].
2010 Mar-Apr
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:55:21 UTC 2023
Edited
by admin
on Fri Dec 15 15:55:21 UTC 2023
Record UNII
H9490V5216
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
Code System Code Type Description
PUBCHEM
42503
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID20973227
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
SMS_ID
100000090326
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
ECHA (EC/EINECS)
260-874-6
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
EVMPD
SUB11828MIG
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL325109
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
CAS
57645-91-7
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
FDA UNII
H9490V5216
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
NCI_THESAURUS
C83629
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY
MERCK INDEX
m3612
Created by admin on Fri Dec 15 15:55:21 UTC 2023 , Edited by admin on Fri Dec 15 15:55:21 UTC 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY