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	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Identifiers
	IUPAC name 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine;
CAS Number	2058-52-8 ;
PubChem CID	16351;
ChemSpider	15510 ;
UNII	Z05HCY0X1T;
KEGG	D01597 ;
ChEBI	CHEBI:108591;
ChEMBL	ChEMBL304902 ;
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 ; Key:KAAZGXDPUNNEFN-UHFFFAOYSA-N ;
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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]

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]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ 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): 95–99. PMID 8105359.
^ 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.
^ ^a ^b 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. S2CID 54246576.
^ ^a ^b Geller V, Gorzaltsan I, Shleifer T, Belmaker RH, Bersudsky Y (December 2005). "Clotiapine compared with chlorpromazine in chronic schizophrenia". Schizophrenia Research. 80 (2–3): 343–347. doi:10.1016/j.schres.2005.07.007. PMID 16126373. S2CID 22340010.
^ 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): 945–947. PMID 4939661.
^ ^a ^b Carpenter S, Berk M, Rathbone J (October 2004). "Clotiapine for acute psychotic illnesses". The Cochrane Database of Systematic Reviews. 2004 (4): CD002304. doi:10.1002/14651858.CD002304.pub2. PMC 8985500. PMID 15495032.
^ Mannocchi G, Pantano F, Tittarelli R, Catanese M, Umani Ronchi F, Busardò FP (2015) Development and Validation of a GC-MS Method for the Detection and Quantification of Clotiapine in Blood and Urine Specimens and Application to a Postmortem Case. Int J Anal Chem 2015 ():972480. DOI:10.1155/2015/972480 PMID: 26236337

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] 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): 95–99. PMID 8105359.

[Schmutz-3] 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.

[forg-4] 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. S2CID 54246576.

[ClotChlor-5] Geller V, Gorzaltsan I, Shleifer T, Belmaker RH, Bersudsky Y (December 2005). "Clotiapine compared with chlorpromazine in chronic schizophrenia". Schizophrenia Research. 80 (2–3): 343–347. doi:10.1016/j.schres.2005.07.007. PMID 16126373. S2CID 22340010.

[6] 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): 945–947. PMID 4939661.

[Ber2004-7] Carpenter S, Berk M, Rathbone J (October 2004). "Clotiapine for acute psychotic illnesses". The Cochrane Database of Systematic Reviews. 2004 (4): CD002304. doi:10.1002/14651858.CD002304.pub2. PMC 8985500. PMID 15495032.

[pmid26236337-8] Mannocchi G, Pantano F, Tittarelli R, Catanese M, Umani Ronchi F, Busardò FP (2015) Development and Validation of a GC-MS Method for the Detection and Quantification of Clotiapine in Blood and Urine Specimens and Application to a Postmortem Case. Int J Anal Chem 2015 ():972480. DOI:10.1155/2015/972480 PMID: 26236337

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol Xanomeline/trospium chloride
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (Tricyclic antidepressants (TCAs))	Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Batelapine Beloxepin Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mirtazapine Monometacrine Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Cidoxepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Perlapine Phenindamine Pimethixene Pirolate Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Anticholinergics	Darenzepine Dipitramine Nuvenzepine Pirenzepine Profenamine Rispenzepine Siltenzepine Telenzepine Tripitramine Tropatepine Zolenzepine
Others	Adosopine Aminopromazine Atiprosin Benzoctamine Botiacrine Carvedilol Cyclobenzaprine Damotepine Elanzepine Fluradoline Methylene blue Monatepil Oxetorone Pipazethate P7C3 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole