Clopenthixol

Structural formula
	( Z ) -isomer (top) and ( E ) -isomer (bottom)
General
Non-proprietary name	Clopenthixol
other names	cis , trans -2- {4- [3- (2-chlorothioxanthen-9-ylidene) propyl] piperazin-1-yl} ethanol (mixture of isomers) ; ( Z , E ) -2- {4- [3- (2-chlorothioxanthen-9-ylidene) propyl] piperazin-1-yl} ethanol (mixture of isomers) ;
Molecular formula	C 22 H 25 ClN 2 OS
External identifiers / databases
EC number	213-566-0
ECHA InfoCard	100.012.333
PubChem	12454
ChemSpider	11945
Wikidata	Q413000
Drug information
ATC code	N05 AF02
Drug class	Antipsychotic
properties
Molar mass	400.97 g · mol -1 ( cis , trans -Clopenthixol) ; 473.89 g · mol -1 ( cis , trans -Clopenthixol · dihydrochloride) ;
Melting point	250–260 ° C ( cis , trans -Clopenthixol · dihydrochloride) ; 84-84 ° C ( cis -clopenthixol) ; 250–260 ° C ( cis -clopenthixol · dihydrochloride) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	226 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Clopenthixol is a mixture of two isomeric polycyclic organic chemical compounds from the group of thioxanthenes . Before it was withdrawn from the market in 2000, it was used as a drug , specifically as a neuroleptic in the treatment of psychoses . Clopenthixol is a dopamine - and serotonin - inhibitor . Clopenthixol was first marketed as part of a drug in 1961 by Lundbeck under the name Sordinol .

Clinical information

application areas

Clopenthixol has been used in the treatment of psychosis to suppress delusional ideas , hallucinations, and thought disorders . Clopenthixol was also used for psychomotor agitation and mania .

Therapeutic value

Clopenthixol is considered to be a moderately strong neuroleptic with a neuroleptic potency of approx. 2 to 3.

unwanted effects

Common undesirable effects include extrapyramidal disorders ( akathisia , parkinsonoid ). Furthermore, drowsiness, a lowering of the seizure threshold , dry mouth, accommodation disorders , drop in blood pressure when changing position, weight gain or the absence of menstruation can occur.

pharmacology

Clopenthixol acts as an antagonist on the dopamine receptors D ₁ and D ₂ and on serotonin receptors ( 5-HT ₂ ). Clopenthixol also inhibits adrenoceptors and acetylcholine receptors to a lesser extent .

Clopenthixol is a mixture of isomers and consists of a pharmacologically active cis isomer [synonym: ( Z ) -Clopenthixol] and the inactive trans isomer [synonym: ( E ) -Clopenthixol]. The mixture of cis- and trans- cyclopenthixol has about half the neuroleptic potency of cis- cyclopenthixol, but has the same antipsychotic effect, but is more sedating . The cis -Clopenthixol will zuclopenthixol called and represents an independent drug.

History

Clopenthixol was marketed in 1961 by the Danish company Lundbeck under the name Sordinol and sold in Germany under license by Bayer under the name Ciatyl . Clopenthixol was first mentioned in the accessible scientific literature in 1962. In 2000 Bayer started Ciatyl. taken off the market and replaced by a preparation with the effective cis - ( Z ) - isomer zuclopenthixol (trade name: Ciatyl-Z).

Individual evidence

↑ ^a ^b ^c The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , pp. 402-403.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on Clopenthixol in the ChemIDplus database of the United States National Library of Medicine (NLM)
^ ^A ^b ^c ^d Franz von Bruchhausen, Siegfried Ebel, August W Frahm, Eberhard Hackenthal (eds.): Hager's handbook of pharmaceutical practice. Volume 4: Substances AK. 5th edition. Springer, Heidelberg 1999, ISBN 3-540-52688-9 . ( limited preview in Google Book search)
↑ A. Gravem, E. Engstrand, RJ Guleng: cis (Z) and -clopenthixol clopenthixol (Sordinol) in chronic psychotic patients. A double-blind clinical investigation. In: Acta Psychiatr Scand. 58, 1978, pp. 384-388, PMID 362830 .
↑ C. Massaut, J. Chantraine, E. Meurice et al: Étude clinique de 162 malades traités par un nouveau neuroleptique: le clopenthixol. In: Acta Neurol Belg. 62, 1962, pp. 651-661. PMID 13933392 .

[MerckIndex-1] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , pp. 402-403.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ChemIDplus-3] Entry on Clopenthixol in the ChemIDplus database of the United States National Library of Medicine (NLM)

[hager-4] A ^b ^c ^d Franz von Bruchhausen, Siegfried Ebel, August W Frahm, Eberhard Hackenthal (eds.): Hager's handbook of pharmaceutical practice. Volume 4: Substances AK. 5th edition. Springer, Heidelberg 1999, ISBN 3-540-52688-9 . ( limited preview in Google Book search)

[5] A. Gravem, E. Engstrand, RJ Guleng: cis (Z) and -clopenthixol clopenthixol (Sordinol) in chronic psychotic patients. A double-blind clinical investigation. In: Acta Psychiatr Scand. 58, 1978, pp. 384-388, PMID 362830 .

[6] C. Massaut, J. Chantraine, E. Meurice et al: Étude clinique de 162 malades traités par un nouveau neuroleptique: le clopenthixol. In: Acta Neurol Belg. 62, 1962, pp. 651-661. PMID 13933392 .