Chemistry: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]
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]
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
- ↑ "Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy". Health and Quality of Life Outcomes 1: 46. September 2003. doi:10.1186/1477-7525-1-46. PMID 14521717.
- ↑ "Anwendung, Wirkung, Nebenwirkungen" (in de). October 17, 2016. https://www.gelbe-liste.de/wirkstoffe/Alizaprid_21923.
- ↑ 3.0 3.1 Mutschler Arzneimittelwirkungen (11 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. 2020. pp. 580. ISBN 978-3-8047-3663-4.
- ↑ Pharmaceutical Substances, 5th Edition: Syntheses, Patents and Applications of the most relevant APIs. Georg Thieme Verlag. 2014. p. 41. ISBN 978-3-13-179525-0.
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