Clotiapine

Clotiapine (Entumine) is an atypical antipsychotic^[2] of the dibenzothiazepine chemical class.^[3] It was first introduced in a few European countries (namely, Belgium, Italy, Spain and Switzerland), Argentina, Taiwan and Israel in 1970.^[4]

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	BR: Class C1 (Other controlled substances)[1] In general: ℞ (Prescription only)
Identifiers
IUPAC name 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine
CAS Number	2058-52-8 N
PubChem CID	16351
ChemSpider	15510 Y
UNII	Z05HCY0X1T
KEGG	D01597 Y
ChEBI	CHEBI:108591
ChEMBL	ChEMBL304902 Y
CompTox Dashboard (EPA)	DTXSID5022851
ECHA InfoCard	100.016.512
Chemical and physical data
Formula	C18H18ClN3S
Molar mass	343.87 g·mol−1
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)

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.^[5] Despite the relativity high rate of undesired 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.^[4][5][6] A systematic review performed by Cochrane compared clotiapine with other antipsychotic drugs:

Clotiapine compared to other antipsychotic drugs for acute psychotic illnesses^[7]

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.[7]
Outcome Findings in words Findings in numbers Quality of evidence General clinical impression No significant improvement There is no clear difference between people given clotiapine and those receiving other antipsychotic drugs for acute psychotic illnesses. These findings are based on data of low quality. RR 0.88 (0.39 to 1.98) Low Not well enough to be discharged Clotiapine is not clearly different to other antipsychotic drugs for this outcome - for people who are acutely unwell. These findings are based on data of low quality. RR 1.04 (0.93 to 1.16) Low Adverse effects Movement disorders - use of antiparkinsonian medication Clotiapine may reduce the use of antiparkinsonian drugs - implying that clotiapine causes less of this effect, but, at present it is not possible to be confident about the difference between the two treatments and data supporting this finding are very limited. RR 0.43 (0.05 to 3.53) Very low Seizure Clotiapine may increase the risk of fits, but, the difference between the two treatments is not clear. This finding is based on data of low quality. RR 3.67 (0.16 to 84.66) Low Satisfaction with care Leaving the study early - any reason There is no clear difference between people given clotiapine and those receiving other antipsychotics for acute psychotic illnesses. These findings are based on data of low quality. RR 2.09 (0.81 to 5.42) Low No study reported any data on outcomes as sedation and information relating to behavioral outcomes such as tranquillisation. Clotiapine increases very fast weight, like approximately in 6 or 7 days of the start, so it is convenient to speak with your doctor it this happens.

A fatal case of urinary retention associated with this drug has been reported in literature.^[8]