Alizapride

Alizapride (Litican, Plitican, Superan, Vergentan) is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting. It is structurally related to metoclopramide and other benzamides.^[1]

Alizapride

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, IM, IV
ATC code	A03FA05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	3 hours
Excretion	Renal
Identifiers
IUPAC name N-[(1-Allylpyrrolidin-2-yl)methyl]-6-methoxy-1H-benzo[d] [1,2,3]triazole-5-carboxamide
CAS Number	59338-93-1 Y
PubChem CID	43008
DrugBank	DB01425 Y
ChemSpider	39202 Y
UNII	P55703ZRZY
KEGG	D07102 Y
ChEMBL	ChEMBL290194 Y
CompTox Dashboard (EPA)	DTXSID10866755
ECHA InfoCard	100.056.082
Chemical and physical data
Formula	C16H21N5O2
Molar mass	315.377 g·mol−1
3D model (JSmol)	Interactive image
SMILES C=CCN1CCCC1CNC(=O)c3cc2nn[nH]c2cc3OC
InChI 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) Y Key:KSEYRUGYKHXGFW-UHFFFAOYSA-N Y
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Mechanism

Alizapride acts on the vomiting center by blocking D2 dopamine receptors.^[2]

Since alizapride is able to cross the blood-brain barrier, adverse effects may include temporary extrapyramidal motor disorders such as acute dystonia and dyskinesia.^[3]

It has a plasma half-life of 3 hours.^[3]

Synthesis

The synthesis of Alizapride happens in multiple steps:^[4]

Synthesis of Alacepril

4-Aminosalicylic acid is first methylated using dimethyl sulfate. A nitro group is then introduced that is reduced using Raney nickel to afford an amino group. The two amino groups are then closed to a triazole ring using sodium nitrite and hydrochloric acid. This is then condensed with 1-allyl-2-aminomethylpyrrolidine to afford Alizapride.