Clotiapine: Difference between revisions

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{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460045350
| IUPAC_name = 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,5]benzothiazepine
| image = Clotiapine.png
| width = 200


<!--Clinical data-->
| tradename = Etumina, Etumine, Entumin, Etomine, Entumine
| Drugs.com = {{drugs.com|international|clotiapine}}
| pregnancy_category = 
| legal_status = Rx-only
| routes_of_administration = Oral, Intravenous and [[Intramuscular]]
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 2058-52-8
| ATC_prefix = N05
| ATC_suffix = AH06
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 304902
| PubChem = 16351
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 15510
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z05HCY0X1T
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01597
<!--Chemical data-->
| C=18 | H=18 | Cl=1 | N=3 | S=1
| molecular_weight = 343.87 g/mol
| smiles = Clc2ccc1Sc4c(/N=C(\c1c2)N3CCN(C)CC3)cccc4
| InChI = 1/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
| InChIKey = KAAZGXDPUNNEFN-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KAAZGXDPUNNEFN-UHFFFAOYSA-N
}}
__NOTOC__
{{SI}}
{{CMG}}
==Overview==
'''Clotiapine''' ('''Entumine''') is an [[atypical antipsychotic]]<ref>{{cite pmid|8105359}}</ref> of the [[dibenzothiazepine]] [[chemical class]].<ref name="Schmutz">{{cite doi|10.1002/hlca.19670500131}}</ref> It was first introduced in a few European countries (namely, [[Belgium]], [[Italy]], [[Spain]] and [[Switzerland]]), [[Argentina]], [[Taiwan]] and [[Israel]] in 1970.<ref name = forg/>
Some sources regard clotiapine as a [[typical antipsychotic]] rather than [[Atypical antipsychotic|atypical]] due to its high incidence of [[extrapyramidal side effects]] compared to the atypicals like clozapine and quetiapine, to which it is structurally related.<ref name = ClotChlor>{{cite journal|title=Clotiapine compared with chlorpromazine in chronic schizophrenia|journal=Schizophrenia Research|volume=80|issue=2-3|pages=343-347|author=Geller, V; Gorzaltsan, I; Shleifer, T; Belmaker, RH; Bersudsky, Y|pmid=16126373|date=December 2005|doi=10.1016/j.schres.2005.07.007}}</ref> 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.<ref name = ClotChlor/><ref>{{cite journal|title=chlorpromazine, clotiapine and thioridazine--a comparative clinical trial on Bantu psychotic patients|journal=South African Medical Journal|date=August 1971|volume=45|issue=34|pages=945-947|pmid=4939661|url=http://archive.samj.org.za/1971%20VOL%20XLV%20Jul-Dec/Articles/08%20August/4.3%20CHLORPROMOZAINE,%20CLOTIAPINE%20AND%20THIORIDAZINE%20-%20A%20COMPARATIVE%20CLINICAL%20TRIAL%20AND%20BANTU%20PSYCHOT.pdf|format=PDF|author=Van Wyk, AJ; Marais, GF}}</ref><ref name = forg>{{cite journal|title=Clotiapine: Another forgotten treasure in psychiatry?|journal=European Neuropsychopharmacology|volume=7|issue=Suppl 2|pages=S217|doi=10.1016/S0924-977X(97)88712-3|date=September 1997|author=Lokshin, P; Kotler, M; Belmaker, RH}}</ref>
==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 ().<ref name="Schmutz" />
[[File:Clothiapine0.png|400px]]
==References==
{{reflist|2}}
{{Antipsychotics}}
{{Adrenergics}}
{{Cholinergics}}
{{Dopaminergics}}
{{Histaminergics}}
{{Serotonergics}}
{{Piperazines}}
{{Tricyclics}}
[[Category:Atypical antipsychotics]]
[[Category:Piperazines]]
[[Category:Drug]]

Revision as of 17:58, 9 April 2015

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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC18H18ClN3S
Molar mass343.87 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)


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

Overview

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]

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 schizophrenic patients according to a number of psychiatrists with clinical experience with it, some weak clinical evidence supports this view too.[4][5][3]

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 ().[2]

References

  1. ↑ PMID 8105359 (PMID 8105359)
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  2. ↑ 2.0 2.1 Template:Cite doi
  3. ↑ 3.0 3.1 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. ↑ 4.0 4.1 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.
  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. 45 (34): 945–947. PMID 4939661.

Template:Piperazines Template:Tricyclics

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