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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 of ALIZAPRIDE HYDROCHLORIDE

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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 200.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Limican

Approved Use

Alizapride is used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.
PubMed

PubMed

TitleDatePubMed
Activity of a new antiemetic agent: alizapride. A randomized double-blind crossover controlled trial.
1988
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
Prevention of emesis by tropisetron (Navoban) in children receiving cytotoxic therapy for solid malignancies.
1994 Oct
Patents

Patents

CN1418624A
2
EP1954244A1
8
US6927036
2

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 17:14:57 GMT 2023
Edited
by admin
on Fri Dec 15 17:14:57 GMT 2023
Record UNII
41BT72BOQ7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALIZAPRIDE HYDROCHLORIDE
MART.   MI   WHO-DD  
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
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C200683
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID20974759
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
SMS_ID
100000088880
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
DRUG BANK
DBSALT000918
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
CAS
59338-87-3
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
PUBCHEM
6410734
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
FDA UNII
41BT72BOQ7
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
EVMPD
SUB00345MIG
Created by admin on Fri Dec 15 17:14:57 GMT 2023 , Edited by admin on Fri Dec 15 17:14:57 GMT 2023
PRIMARY
Related Record Type Details
Structure of ALIZAPRIDE HYDROCHLORIDE, (R)-
ENANTIOMER -> RACEMATE
Structure of ALIZAPRIDE
PARENT -> SALT/SOLVATE
Structure of ALIZAPRIDE HYDROCHLORIDE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of ALIZAPRIDE
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