Clotiapine

Clotiapine

Clinical data
Trade names	Etumina, Etumine, Entumin, Etomine, Entumine
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, Intravenous and Intramuscular
ATC code	N05AH06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,5]benzothiazepine
CAS Number	2058-52-8 N
PubChem CID	16351
ChemSpider	15510 Y
UNII	Z05HCY0X1T
KEGG	D01597 Y
ChEMBL	ChEMBL304902 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C18H18ClN3S
Molar mass	343.87 g/mol
3D model (JSmol)	Interactive image
SMILES Clc2ccc1Sc4c(/N=C(\c1c2)N3CCN(C)CC3)cccc4
InChI InChI=1S/C18H18ClN3S/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3 Y Key:KAAZGXDPUNNEFN-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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Evidence Based Medicine
Cochrane Collaboration on Clotiapine Bandolier on Clotiapine TRIP on Clotiapine
Clinical Trials
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Commentary
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Definitions
Definitions of Clotiapine
Patient Resources / Community
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Healthcare Provider Resources
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Continuing Medical Education (CME)
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International
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Business
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Experimental / Informatics
List of terms related to Clotiapine

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Clotiapine (Entumine) is an atypical antipsychotic of the dibenzothiazepine chemical class. It was first introduced in a few European countries (namely, Belgium, Italy, Spain and Switzerland), Argentina, Taiwan and Israel in 1970.

Some sources regard clotiapine as a typical antipsychotic rather than atypical due to its high incidence of extrapyramidal side effects compared to the atypicals like clozapine and quetiapine, to which it is structurally related.Despite its profile of a relatively high incidence of extrapyramidal side effects it has demonstrated efficacy in treatment-resistant schizophrenic patients according to a number of psychiatrists with clinical experience with it, some weak clinical evidence supports this view too.

Synthesis

Ullmann condensation of the substituted thiosalyciclic acid with ortho-chloronitrobenzene results in the displacement of chlorine by thiophenoxide and the formation of the thioether . The nitro group in this last intermediate is then reduced to an aniline ; the resulting amino acid is then cyclized thermally to the lactam . Treatment of that with phosphorus oxychloride gives the imino chloride. Reaction with N-methylpiperazine leads to the replacement of chlorine by nitrogen and the formation of clothiapine .