| Verifiedrevid | 477317609 |
|---|---|
| Iupac name | N-[(1-Allylpyrrolidin-2-yl)methyl]-6-methoxy-1H-benzo[d][1,2,3]triazole-5-carboxamide |
| Legal status | Rx-only |
| Routes of administration | Oral, IM, IV |
| Elimination half-life | 3 hours |
| Excretion | Renal |
| Cas number | 59338-93-1 |
| Atc prefix | A03 |
| Atc suffix | FA05 |
| Pubchem | 43008 |
| Drugbank | DB01425 |
| Chemspiderid | 39202 |
| Unii | P55703ZRZY |
| Kegg | D07102 |
| Chembl | 290194 |
| C | 16 |
| H | 21 |
| N | 5 |
| O | 2 |
| Smiles | C=CCN1CCCC1CNC(=O)c3cc2nn[nH]c2cc3OC |
| Stdinchi | 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) |
| Stdinchikey | KSEYRUGYKHXGFW-UHFFFAOYSA-N |
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 blocks D2 dopamine receptors in the vomiting center.[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
- ^ 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
- ^ Online GL (October 17, 2016). "Anwendung, Wirkung, Nebenwirkungen" (in German). Gelbe Liste Online. Retrieved April 30, 2025.
- ^ Geisslinger G, Menzel S, Gundermann T, Roth P (2020). Mutschler Arzneimittelwirkungen. 11 ed. Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 580. ISBN 978-3-8047-3663-4.
- ^ 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.