Alizapride

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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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]

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.

References

1. Ballatori E, Roila F (September 2003). "Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy". Health and Quality of Life Outcomes. 1: 46. doi: 10.1186/1477-7525-1-46 . PMC   212194 . PMID   14521717.
2. Online GL (October 17, 2016). "Anwendung, Wirkung, Nebenwirkungen". Gelbe Liste Online (in German). Retrieved April 30, 2025.
3. Geisslinger G, Menzel S, Gundermann T, Roth P (2020). Mutschler Arzneimittelwirkungen (11 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 580. ISBN   978-3-8047-3663-4.
4. Kleemann A, Engel J, Kutscher B, Reichert D (2014). Pharmaceutical Substances, 5th Edition: Syntheses, Patents and Applications of the most relevant APIs. Georg Thieme Verlag. p. 41. ISBN   978-3-13-179525-0.