Alizapride
| File:Alizapride.svg | |
| File:3D Alizapride.png | |
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| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral, IM, IV |
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| Pharmacokinetic data | |
| Elimination half-life | 3 hours |
| Excretion | Renal |
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| E number | {{#property:P628}} |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C16H21N5O2 |
| Molar mass | 315.377 g·mol−1 |
| 3D model (JSmol) | |
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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
[edit | edit source]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
[edit | edit source]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
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