Metiapine

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]

Metiapine

Clinical data
Drug class	Typical antipsychotic
Identifiers
IUPAC name 8-methyl-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine
CAS Number	5800-19-1
PubChem CID	22047
ChemSpider	20718
UNII	775D6D91J8
KEGG	D02672
ChEMBL	ChEMBL2106892
CompTox Dashboard (EPA)	DTXSID7020891
Chemical and physical data
Formula	C19H21N3S
Molar mass	323.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(C=C1)SC3=CC=CC=C3N=C2N4CCN(CC4)C
InChI 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

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]

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

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 814–. ISBN 978-1-4757-2085-3.
2. Zare M, Bazrafshan A (March 2017). "Chlorpromazine versus metiapine for schizophrenia". The Cochrane Database of Systematic Reviews. 2017 (3): CD011655. doi:10.1002/14651858.CD011655.pub2. PMC 6464499. PMID 28349512.
3. Baldessarini RJ (1985). Chemotherapy in psychiatry : principles and practice (Rev. and enl. ed.). Cambridge, Massachusetts: Harvard University Press. ISBN 0674113837.
4. Ishar MP, Faruk A (2006). Syntheses of organic medicinal compounds. Oxford: Alpha Science International. ISBN 184265280X.