Alizapride

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Chemical compound

title: "Alizapride" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antiemetics", "dopamine-antagonists", "motility-stimulants", "salicylamide-ethers", "benzotriazoles", "pyrrolidines", "allylamines"] description: "Chemical compound" topic_path: "general/antiemetics" source: "https://en.wikipedia.org/wiki/Alizapride" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 477317609 | IUPAC_name = N-[(1-Allylpyrrolidin-2-yl)methyl]-6-methoxy-1H-benzo[d] [1,2,3]triazole-5-carboxamide | image = Alizapride.svg | image_class = skin-invert-image | image2 = 3D Alizapride.png | image_class2 = bg-transparent | tradename = | Drugs.com = | pregnancy_category = | legal_status = Rx-only | routes_of_administration = Oral, IM, IV | bioavailability = | metabolism = | elimination_half-life = 3 hours | excretion = Renal | CAS_number_Ref = | CAS_number = 59338-93-1 | ATC_prefix = A03 | ATC_suffix = FA05 | PubChem = 43008 | DrugBank_Ref = | DrugBank = DB01425 | ChemSpiderID_Ref = | ChemSpiderID = 39202 | UNII_Ref = | UNII = P55703ZRZY | KEGG_Ref = | KEGG = D07102 | ChEMBL_Ref = | ChEMBL = 290194 | C=16 | H=21 | N=5 | O=2 | smiles = C=CCN1CCCC1CNC(=O)c3cc2nn[nH]c2cc3OC | StdInChI_Ref = | 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_Ref = | 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.

Mechanism

Alizapride acts on the vomiting center by blocking D2 dopamine receptors.

Since alizapride is able to cross the blood-brain barrier, adverse effects may include temporary extrapyramidal motor disorders such as acute dystonia and dyskinesia.

It has a plasma half-life of 3 hours.

Synthesis

The synthesis of Alizapride happens in multiple steps:

::figure[src="https://upload.wikimedia.org/wikipedia/commons/3/35/Alizaprid_Synthesis.svg" caption="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

References

  1. (September 2003). "Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy". Health and Quality of Life Outcomes.
  2. (October 17, 2016). "Anwendung, Wirkung, Nebenwirkungen".
  3. (2020). "Mutschler Arzneimittelwirkungen". Wissenschaftliche Verlagsgesellschaft.
  4. (2014). "Pharmaceutical Substances, 5th Edition: Syntheses, Patents and Applications of the most relevant APIs". Georg Thieme Verlag.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

antiemeticsdopamine-antagonistsmotility-stimulantssalicylamide-ethersbenzotriazolespyrrolidinesallylamines