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Alizapride

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Alizapride
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral,IM,IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Eliminationhalf-life3 hours
ExcretionRenal
Identifiers
  • N-[(1-Allylpyrrolidin-2-yl)methyl]-6-methoxy-1H-benzo[d] [1,2,3]triazole-5-carboxamide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.056.082Edit this at Wikidata
Chemical and physical data
FormulaC16H21N5O2
Molar mass315.377 g·mol−1
3D model (JSmol)
  • C=CCN1CCCC1CNC(=O)c3cc2nn[nH]c2cc3OC
  • 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) checkY
  • Key:KSEYRUGYKHXGFW-UHFFFAOYSA-N checkY
  (verify)

Alizapride (Litican,Plitican,Superan,Vergentan) is adopamine antagonist withprokinetic andantiemetic effects used in the treatment ofnausea andvomiting, includingpostoperative nausea and vomiting. It is structurally related tometoclopramide and otherbenzamides.[1]

Mechanism

[edit]

Alizapride acts on thevomiting center by blockingD2 dopamine receptors.[2]

Since alizapride is able to cross the blood-brain barrier, adverse effects may include temporary extrapyramidal motor disorders such as acutedystonia anddyskinesia.[3]

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

Synthesis

[edit]

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

Synthesis of Alacepril
Synthesis of Alacepril

4-Aminosalicylic acid is firstmethylated usingdimethyl sulfate. Anitro group is then introduced that is reduced usingRaney nickel to afford an amino group. The two amino groups are then closed to atriazole ring usingsodium nitrite andhydrochloric acid. This is thencondensed with 1-allyl-2-aminomethylpyrrolidine to afford Alizapride.

References

[edit]
  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). RetrievedApril 30, 2025.
  3. ^abGeisslinger 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.
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