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=CC(N)=C(Cl)C=C1C(=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	C20H24ClN3O2
Molecular Weight	373.876
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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	( + / - )

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 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14871277	Antagonist 2849		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 8583	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.

C_max

Value	Dose	Co-administered	Analyte	Population
2073 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20598654/	1.36 mg single, oral dose: 1.36 mg route of administration: Oral experiment type: SINGLE co-administered:		CLEBOPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
215 μg/L EXPERIMENT https://link.springer.com/article/10.1007/BF03258378	15.171 mg single, intravenous dose: 15.171 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CLEBOPRIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
8045 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20598654/	1.36 mg single, oral dose: 1.36 mg route of administration: Oral experiment type: SINGLE co-administered:		CLEBOPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
842 ng × h/mL EXPERIMENT https://link.springer.com/article/10.1007/BF03258378	15.171 mg single, intravenous dose: 15.171 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CLEBOPRIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
5.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20598654/	1.36 mg single, oral dose: 1.36 mg route of administration: Oral experiment type: SINGLE co-administered:	CLEBOPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.5 h EXPERIMENT https://link.springer.com/article/10.1007/BF03258378	15.171 mg single, intravenous dose: 15.171 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CLEBOPRIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.5 h EXPERIMENT https://link.springer.com/article/10.1007/BF03258378	15.171 mg single, intravenous dose: 15.171 mg route of administration: Intravenous experiment type: SINGLE co-administered:	N-DESBENZYL-CLEBOPRIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.9 mg/kg single, intravenous Highest studied dose Dose: 0.9 mg/kg Route: intravenous Route: single Dose: 0.9 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/	Other AEs: Somnolence, Diarrhea... Other AEs: Somnolence (grade 1-2) Diarrhea Extrapyramidal symptoms Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/
1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8419802/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8419802/	Disc. AE: Dyskinesia... AEs leading to discontinuation/dose reduction: Dyskinesia Sources: https://pubmed.ncbi.nlm.nih.gov/8419802/
1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1557073/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1557073/	Disc. AE: Parkinson's syndrome... AEs leading to discontinuation/dose reduction: Parkinson's syndrome Sources: https://pubmed.ncbi.nlm.nih.gov/1557073/
0.68 mg single, oral Studied dose Dose: 0.68 mg Route: oral Route: single Dose: 0.68 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31145322/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31145322/	Disc. AE: Dystonic reaction... AEs leading to discontinuation/dose reduction: Dystonic reaction Sources: https://pubmed.ncbi.nlm.nih.gov/31145322/

AEs

AE	Significance	Dose	Population
Diarrhea		0.9 mg/kg single, intravenous Highest studied dose Dose: 0.9 mg/kg Route: intravenous Route: single Dose: 0.9 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/
Extrapyramidal symptoms		0.9 mg/kg single, intravenous Highest studied dose Dose: 0.9 mg/kg Route: intravenous Route: single Dose: 0.9 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/
Somnolence	grade 1-2	0.9 mg/kg single, intravenous Highest studied dose Dose: 0.9 mg/kg Route: intravenous Route: single Dose: 0.9 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1606084/
Dyskinesia	Disc. AE	1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8419802/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8419802/
Parkinson's syndrome	Disc. AE	1.5 mg 3 times / day multiple, oral Recommended Dose: 1.5 mg, 3 times / day Route: oral Route: multiple Dose: 1.5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1557073/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1557073/
Dystonic reaction	Disc. AE	0.68 mg single, oral Studied dose Dose: 0.68 mg Route: oral Route: single Dose: 0.68 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31145322/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31145322/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 OATP1B3 961 OATP1B1 1079	CYP2C19 1119 CYP1A2 1197 CYP2B6 776 CYP2C8 810	CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzI1MTA5In19	inconclusive [IC50 3.1623 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDMyNTEwOSJ9fQ==	no [IC50 12.5893 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDMyNTEwOSJ9fQ==	no [IC50 7.9433 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDMyNTEwOSJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzI1MTA5In19	yes [IC50 0.0126 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTkyNDgifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTkyNDgifX0=	yes [Inhibition 10 uM]
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/25183402/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/25183402/	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	minor
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	minor
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	minor
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	minor
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21841964/	minor

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
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.	2010-08-01	20598654
[A new method of investigation of "child's" behavior (infant-mother attachment) of newborn rats].	2010-05-18	20469600
A randomized, controlled, double-blind trial of the adjunct use of Clebopride in polyethylene glycol electrolyte (PEG) solution for colonoscopy preparation.	2010-01	20305329
Acute hemifacial dystonia possibly induced by clebopride.	2009-06-11	19512962
Acute oculogyric crisis in a patient taking clebopride.	2008	18344644
Effects of vehicles and enhancers on transdermal delivery of clebopride.	2007-09	17958335
[Acute laryngeal dystonia due to clebopride simulating allergic reaction].	2007-07-07	17678608
Effect of clebopride, antidopaminergic gastrointestinal prokinetics, on cardiac repolarization.	2007-03-17	17365143
Effectiveness and safety of levosulpiride in the treatment of dysmotility-like functional dyspepsia.	2007-03	18360622
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.	2007	21673949
Etiological and therapeutical observations in a case of belly dancer's dyskinesia.	2006-09	16830316
Etiological and therapeutical observations in a case of belly dancer's dyskinesia.	2005-02	15455446
Progressive supranuclear palsy syndrome induced by clebopride.	2004-04	15077251
Review article: clinical implications of enteric and central D2 receptor blockade by antidopaminergic gastrointestinal prokinetics.	2004-02-15	14871277
Stereocontrolled dopamine receptor binding and subtype selectivity of clebopride analogues synthesized from aspartic acid.	2003-10-06	12951112
[Rabbit syndrome due to clebopride].	2003-06-07	12812712
Dopamine antagonists during parturition disrupt maternal care and the retention of maternal behavior in rats.	2002-11	12213533
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
NMDA receptor antagonists inhibit catalepsy induced by either dopamine D1 or D2 receptor antagonists.	1993-06-11	8359205
[Drug-induced extrapyramidal syndrome. Apropos of 22 cases].	1987-02	3565961
[Clebopride, a new orthopramide with potent and selective central antidopaminergic properties].	1978-04	100059
Synthesis and pharmacological properties of a series of antidopaminergic piperidyl benzamides.	1977-03	15078

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 `Mon Mar 31 18:13:18 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:18 GMT 2025`
Record UNII	H9490V5216
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLEBOPRIDE MALATE

Common Name

English

AMICOS

Preferred 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

Clebopride malate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883