ALIZAPRIDE HYDROCHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H21N5O2.ClH
Molecular Weight	351.831
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.COC1=C(C=C2N=NNC2=C1)C(=O)NCC3CCCN3CC=C

InChI

InChIKey=BRECEDGYMYXGNF-UHFFFAOYSA-N

InChI=1S/C16H21N5O2.ClH/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2;/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20);1H

HIDE SMILES / InChI

Molecular Formula	C16H21N5O2
Molecular Weight	315.3702
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://www.drugbank.ca/drugs/DB01425 | http://en.pharmacodia.com/web/drug/1_17054.html

Alizapride is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting. The anti-emetic action of Alizapride is due to its antagonist activity at D2 receptors in the chemoreceptor trigger zone (CTZ) in the central nervous system (CNS)—this action prevents nausea and vomiting triggered by most stimuli. Structurally similar to metoclopramide and, therefore, shares similar other attributes related to emesis and prokinetics.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3397992	Antagonist 2849		200.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nausea and vomiting 19 Sources: http://en.pharmacodia.com/web/drug/1_17054.html https://www.epharmapedia.com/medicine/profile/143124/Limican.html?lang=en&tab=druginfo	Primary		Approved 8583	Limican Approved Use Alizapride is used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.

AUC

Value	Dose	Analyte	Population
1.977 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.533 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.66 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.587 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.706 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.76 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.17 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.573 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7595 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11468033/	3.78 mg/kg single, intravenous dose: 3.78 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
5574 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11468033/	4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
4260.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11468033/	3.97 mg/kg single, intravenous dose: 3.97 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.98 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6827466/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.28 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11468033/	3.78 mg/kg single, intravenous dose: 3.78 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
2.27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11468033/	4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
4.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11468033/	3.97 mg/kg single, intravenous dose: 3.97 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	ALIZAPRIDE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 mg/kg single, intravenous Recommended Dose: 5 mg/kg Route: intravenous Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7826833/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7826833/	Other AEs: Diarrhoea... Other AEs: Diarrhoea (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/7826833/
100 mg single, intramuscular Studied dose Dose: 100 mg Route: intramuscular Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/	Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/
100 mg single, oral Studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/	Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/
4 mg/kg single, intravenous Studied dose Dose: 4 mg/kg Route: intravenous Route: single Dose: 4 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11468033/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11468033/	Sources: https://pubmed.ncbi.nlm.nih.gov/11468033/
100 mg single, rectal Studied dose Dose: 100 mg Route: rectal Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/	unhealthy Health Status: unhealthy Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/	Sources: https://pubmed.ncbi.nlm.nih.gov/6502497/

AEs

AE	Significance	Dose	Population
Diarrhoea	1 pt	5 mg/kg single, intravenous Recommended Dose: 5 mg/kg Route: intravenous Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7826833/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7826833/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UMAT 30 P-gp 1741	HLM 34

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1347076#sid=56463033	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/602162#sid=56463033	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
HLM 34	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22707166/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/720551#sid=56463033

PubMed

Title	Date	PubMed
Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs.	1999-03	10075867
Prevention of emesis by tropisetron (Navoban) in children receiving cytotoxic therapy for solid malignancies.	1994-10	9113122
The role of dopamine (D2), alpha and beta-adrenoceptor receptors in the decrease in gastrointestinal transit induced by dopamine and dopamine-related drugs in the rat.	1993-05-01	8103596
[Comparison of the antiemetic effectiveness of granisetron and alizapride plus dexamethasone in cytostatic therapy].	1991-11-29	1659980
Role of dopamine receptors in gastrointestinal motility.	1989-06	2571179
Manometric study of the activity of alizapride on the motor function of the human sphincter of Oddi.	1988-08	3235478
Comparison of the in-vitro receptor selectivity of substituted benzamide drugs for brain neurotransmitter receptors.	1988-06	2901473
Activity of a new antiemetic agent: alizapride. A randomized double-blind crossover controlled trial.	1988	3048762
Gastro-oesophageal reflux in paediatric patients: studies with alizapride.	1987	3602025
Hypertension and intravenous antidopaminergic drugs.	1985-04-25	3982470
[Hydrolysis of the antiemetic alizapride].	1984	6543307

Patents

Sample Use Guides

In Vivo Use Guide

The treatment duration should not exceed one week.Oral administration: 100-200 mg per day in divided dosesParenteral administration:nausea and vomiting in pre-or post-operative, 50-200 mg, usually intramuscularly within 24 hours.Nausea and vomiting during chemotherapy: 100 mg intravenously 20-30 minutes prior to chemotherapy treatment, followed by 50-100 mg intramuscularly 4-8 hours after the end of chemotherapy.

Route of Administration: Other

In Vitro Use Guide

Alizapride inhibited binding of [3H]spiperone to rat striatal membrane preparations with the IC50 value of 66 nm.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:42:48 GMT 2025` Edited by `admin` on `Mon Mar 31 18:42:48 GMT 2025`
Record UNII	41BT72BOQ7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALIZAPRIDE HYDROCHLORIDE

Common Name

English

LIMICAN

Preferred Name

English

6-METHOXY-N-((1-(2-PROPEN-1-YL)-2-PYRROLIDINYL)METHYL)-1H-BENZOTRIAZOLE-5-CARBOXAMIDE HYDROCHLORIDE

Systematic Name

English

N-(1-ALLYL-2-PYRROLIDINYLMETHYL)-6-METHOXY-1H-BENZOTRIAZOLE-5-CARBOXAMIDE HYDROCHLORIDE

Systematic Name

English

Alizapride hydrochloride [WHO-DD]

Common Name

English

NAUSILEN

Brand Name

English

ALIZAPRIDE HCL

Common Name

English

(±)-N-(1-ALLYL-2-PYRROLIDINYLMETHYL)-6-METHOXY-1H-BENZOTRIAZOLE-5-CARBOXAMIDE HYDROCHLORIDE

Systematic Name

English

VERGENTAN

Brand Name

English

ALIZAPRIDE HYDROCHLORIDE [MI]

Common Name

English

ALIZAPRIDE HYDROCHLORIDE [MART.]

Common Name

English

PLITICAN

Brand Name

English

Code System Code Type Description

MERCK INDEX

m1512