Clotiapine

Clotiapine (Entumine) is an atypical antipsychotic[1] of the dibenzothiazepine chemical class.[2] It was first introduced in a few European countries (namely, Belgium, Italy, Spain and Switzerland), Argentina, Taiwan and Israel in 1970.[3]

Clotiapine
Clinical data
Trade namesEtumina, Etumine, Entumin, Etomine, Entumine
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, Intravenous and Intramuscular
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.512
Chemical and physical data
FormulaC18H18ClN3S
Molar mass343.87 g·mol−1
3D model (JSmol)
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)

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.[4] Despite its profile of a relatively high incidence of extrapyramidal side effects it has demonstrated efficacy in treatment-resistant individuals with schizophrenia according to a number of psychiatrists with clinical experience with it, some weak clinical evidence supports this view too.[3][4][5] A systematic review compared clotiapine with other antipsychotic drugs:

Clotiapine compared to other antipsychotic drugs for acute psychotic illnesses[6]
Summary
There was no evidence to support or refute the use of clotiapine in preference to other antipsychotic drug treatments for management of people with acute psychotic illness.[6]

References
  1. Seminara G, Trassari V, Prestifilippo N, Chiavetta R, Calandra C (June 1993). "[Atypical tricyclic neuroleptics for treatment of schizophrenia. Clothiapine and clozapine]". Minerva Psichiatrica. 34 (2): 95–9. PMID 8105359.
  2. Schmutz J, Künzle F, Hunziker F, Gauch R (1967). "Über in 11-Stellung amino-substituierte Dibenzo[b,f]-1, 4-thiazepine und -oxazepine. 9. Mitteilung über siebengliedrige Heterocyclen". Helvetica Chimica Acta. 50: 245–254. doi:10.1002/hlca.19670500131.
  3. Lokshin, P; Kotler, M; Belmaker, RH (September 1997). "Clotiapine: Another forgotten treasure in psychiatry?". European Neuropsychopharmacology. 7 (Suppl 2): S217. doi:10.1016/S0924-977X(97)88712-3.
  4. Geller V, Gorzaltsan I, Shleifer T, Belmaker RH, Bersudsky Y (December 2005). "Clotiapine compared with chlorpromazine in chronic schizophrenia". Schizophrenia Research. 80 (2–3): 343–7. doi:10.1016/j.schres.2005.07.007. PMID 16126373.
  5. Van Wyk AJ, Marais GF (August 1971). "Chlorpromazine, clotiapine and thioridazine--a comparative clinical trial on Bantu psychotic patients" (PDF). South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde. 45 (34): 945–7. PMID 4939661.
  6. Carpenter S, Berk M, Rathbone J (October 2004). "Clotiapine for acute psychotic illnesses". The Cochrane Database of Systematic Reviews. 4 (4): CD002304. doi:10.1002/14651858.CD002304.pub2. PMID 15495032.
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