ALIZAPRIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H21N5O2
Molecular Weight	315.3702
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KSEYRUGYKHXGFW-UHFFFAOYSA-N

InChI=1S/C16H21N5O2/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)

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	( + / - )

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
[Hydrolysis of the antiemetic alizapride].	1984	6543307
Hypertension and intravenous antidopaminergic drugs.	1985 Apr 25	3982470
Gastro-oesophageal reflux in paediatric patients: studies with alizapride.	1987	3602025
Activity of a new antiemetic agent: alizapride. A randomized double-blind crossover controlled trial.	1988	3048762
Manometric study of the activity of alizapride on the motor function of the human sphincter of Oddi.	1988 Aug	3235478
Comparison of the in-vitro receptor selectivity of substituted benzamide drugs for brain neurotransmitter receptors.	1988 Jun	2901473
Role of dopamine receptors in gastrointestinal motility.	1989 Jun	2571179
[Comparison of the antiemetic effectiveness of granisetron and alizapride plus dexamethasone in cytostatic therapy].	1991 Nov 29	1659980
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
Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs.	1999 Mar	10075867

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:50 UTC 2023` Edited by `admin` on `Fri Dec 15 15:01:50 UTC 2023`
Record UNII	P55703ZRZY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALIZAPRIDE

Official Name

English

Alizapride [WHO-DD]

Common Name

English

alizapride [INN]

Common Name

English

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

Systematic Name

English

(±)-N-((1-ALLYL-2-PYRROLIDINYL)METHYL)-6-METHOXY-1H-BENZOTRIAZOLE-5-CARBOXAMIDE

Systematic Name

English

N-((1-ALLYL-2-PYRROLIDINYL)METHYL)-6-METHOXY-1H-BENZOTRIAZOLE-5-CARBOXAMIDE

Systematic Name

English

ALIZAPRIDE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA03FA05