ALIZAPRIDE HYDROCHLORIDE

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

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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 297 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3397992	Antagonist 2778		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 8429	Limican Approved Use Alizapride is used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.

PubMed

Title	Date	PubMed
Hypertension and intravenous antidopaminergic drugs.	1985 Apr 25	3982470
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 May-Jun	8103596
Prevention of emesis by tropisetron (Navoban) in children receiving cytotoxic therapy for solid malignancies.	1994 Oct	9113122

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 doses Parenteral 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.

Name

Type

Language

ALIZAPRIDE HYDROCHLORIDE

Common 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

LIMICAN

Brand Name

English

PLITICAN

Brand Name

English

Code System Code Type Description

MERCK INDEX

m1512