Metiapine

Chemical compound From Wikipedia, the free encyclopedia

Metiapine is a typical antipsychotic medication of the dibenzothiazepine group.[1][2] There is scarce research on the safety and efficacy of metiapine in humans, though limited human trials exist.[2]

CAS Number
Quick facts Clinical data, Drug class ...
Metiapine
Clinical data
Drug classTypical antipsychotic
Identifiers
  • 8-methyl-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H21N3S
Molar mass323.46 g·mol−1
3D model (JSmol)
  • CC1=CC2=C(C=C1)SC3=CC=CC=C3N=C2N4CCN(CC4)C
  • InChI=1S/C19H21N3S/c1-14-7-8-17-15(13-14)19(22-11-9-21(2)10-12-22)20-16-5-3-4-6-18(16)23-17/h3-8,13H,9-12H2,1-2H3
  • Key:IOEPXYJOHIZYGQ-UHFFFAOYSA-N
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Medical uses

Metiapine has been investigated for the treatment of schizophrenia.[2]

Side effects

Like other typical antipsychotics, it has a high rate of extrapyramidal side effects.[3]

Pharmacology

Metiapine has strong antidopaminergic effects and is classified as a typical (i.e., first-generation) antipsychotic.[3]

Chemistry

Metiapine is a dibenzothiazepine derivative.[2] Like clothiapine, metiapine has a sulfur atom replacing the nitrogen atom found in dibenzodiazepine derivative antipsychotics like clozapine.[3]

Synthesis

Metiapine can be synthesized through the following mechanism:[4]

Metiapine Synthesis

History

Metiapine was first discovered in the 1970s by Marion Merrell Dow (now a part of Sanofi).[2]

Research

A 2017 Cochrane Review provided guidance for a double-blind, randomized controlled trial of metiapine versus chlorpromazine for the treatment of schizophrenia, though the authors acknowledged that it is unlikely that any future trials will investigate the use of metiapine in humans.[2] The available evidence for the use of metiapine is very limited.[2]

References

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