Clotiapine: Difference between revisions

Jump to navigation Jump to search
← Older editNewer edit →
VisualWikitext
Aparna Vuppala (talk | contribs)
nocaptcha, Administrators
6,313 edits
Blanked the page
Aparna Vuppala (talk | contribs)
nocaptcha, Administrators
6,313 edits
No edit summary
Line 1: Line 1:
{{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)


WikiDoc Resources for Clotiapine

Articles

Most recent articles on Clotiapine

Most cited articles on Clotiapine

Review articles on Clotiapine

Articles on Clotiapine in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Clotiapine

Images of Clotiapine

Photos of Clotiapine

Podcasts & MP3s on Clotiapine

Videos on Clotiapine

Evidence Based Medicine

Cochrane Collaboration on Clotiapine

Bandolier on Clotiapine

TRIP on Clotiapine

Clinical Trials

Ongoing Trials on Clotiapine at Clinical Trials.gov

Trial results on Clotiapine

Clinical Trials on Clotiapine at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Clotiapine

NICE Guidance on Clotiapine

NHS PRODIGY Guidance

FDA on Clotiapine

CDC on Clotiapine

Books

Books on Clotiapine

News

Clotiapine in the news

Be alerted to news on Clotiapine

News trends on Clotiapine

Commentary

Blogs on Clotiapine

Definitions

Definitions of Clotiapine

Patient Resources / Community

Patient resources on Clotiapine

Discussion groups on Clotiapine

Patient Handouts on Clotiapine

Directions to Hospitals Treating Clotiapine

Risk calculators and risk factors for Clotiapine

Healthcare Provider Resources

Symptoms of Clotiapine

Causes & Risk Factors for Clotiapine

Diagnostic studies for Clotiapine

Treatment of Clotiapine

Continuing Medical Education (CME)

CME Programs on Clotiapine

International

Clotiapine en Espanol

Clotiapine en Francais

Business

Clotiapine in the Marketplace

Patents on Clotiapine

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[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)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  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

Retrieved from "https://www.wikidoc.org/index.php?title=Clotiapine&oldid=1085489"