U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H25ClN2OS.2ClH
Molecular Weight 473.8883
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLOPENTHIXOL DIHYDROCHLORIDE, TRANS

SMILES

c1ccc2c(c1)/C(=C(/[H])\CCN3CCN(CC3)CCO)/c4cc(ccc4S2)Cl.Cl.Cl

InChI

InChIKey=LPWNZMIBFHMYMX-MONHGIHASA-N
InChI=1S/C22H25ClN2OS.2ClH/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26;;/h1-2,4-8,16,26H,3,9-15H2;2*1H/b18-5+;;

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H25ClN2OS
Molecular Weight 400.9665
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

trans-Clopenthixol is a typical antipsychotic drug of the thioxanthene class. Clopenthixol is composed of a mixture of cis-clopenthixol and trans-clopenthixol. The two isomers do not differ in several pharmacological properties, for instance, anti-noradrenergic effect. However, cis-clopenthixol possesses anti-dopaminergic effects, while trans-Clopenthixol not. Cis-Clopenthixol indicated for the management of the manifestations of schizophrenia and other mental illnesses with disturbances in thinking, emotional reactions and behavior.

Approval Year

PubMed

PubMed

TitleDatePubMed
The bucco-linguo-masticatory syndrome as a side-effect of neuroleptics therapy.
1967
Differential inhibition by dopamine D-1 and D-2 antagonists of circling behaviour induced by dopamine agonists in rats with unilateral 6-hydroxydopamine lesions.
1984 Jul 13
The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria.
1986 Dec
Prolonged oculogyric crisis on addition of nifedipine to neuroleptic medication regime.
1987 Jan
Zuclopenthixol and perphenazine in patients with acute psychotic states. A double-blind multicentre study.
1987 Jul
Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia.
1991 Dec
[acute dystonias in combined abuse of cocaine and neuroleptics].
1994 Nov 26
Central D2 receptor occupancy and effects of zuclopenthixol acetate in humans.
1995 Nov
Effect of some psychotropic drugs and a barbiturate on mycoplasmas.
2000 Apr
Antipsychotic-induced extrapyramidal syndromes. Risperidone compared with low- and high-potency conventional antipsychotic drugs.
2001 Jul
Clozapine and weight gain.
2001 May
Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms.
2003 Jul
Pro-oxidant activity of zuclopenthixol in vivo: differential effect of the drug on brain oxidative status of scopolamine-treated rats.
2004 Aug
Long term results of unilateral posteroventral pallidotomy for antipsychotic drug induced tardive dyskinesia.
2005 Jul
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Fatal exertional heat stroke in a patient receiving zuclopenthixol, quetiapine and benztropine.
2007 Fall
Remission of schizophrenia psychosis and strong reduction of obsessive-compulsive disorder after adding clozapine to aripiprazole.
2009 Nov 13
Severe laryngeal dystonia in a patient receiving zuclopenthixol "Acuphase" and fluoxetine.
2010 Apr
Zuclopenthixol acetate for acute schizophrenia and similar serious mental illnesses.
2012 Apr 18
Simultaneous determination of 25 common pharmaceuticals in whole blood using ultra-performance liquid chromatography-tandem mass spectrometry.
2012 Sep
Paradoxical severe agitation induced by add-on high-doses quetiapine in schizo-affective disorder.
2014 May 15
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:45:41 UTC 2021
Edited
by admin
on Sat Jun 26 08:45:41 UTC 2021
Record UNII
L3KM17324B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOPENTHIXOL DIHYDROCHLORIDE, TRANS
Common Name English
TRANS-CLOPENTHIXOL DIHYDROCHLORIDE
Common Name English
1-PIPERAZINEETHANOL, 4-((3E)-3-(2-CHLORO-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-, DIHYDROCHLORIDE
Common Name English
CLOPENTHIXOL HYDROCHLORIDE, TRANS
Common Name English
Code System Code Type Description
CAS
58045-22-0
Created by admin on Sat Jun 26 08:45:41 UTC 2021 , Edited by admin on Sat Jun 26 08:45:41 UTC 2021
PRIMARY
PUBCHEM
6446379
Created by admin on Sat Jun 26 08:45:41 UTC 2021 , Edited by admin on Sat Jun 26 08:45:41 UTC 2021
PRIMARY
EPA CompTox
58045-22-0
Created by admin on Sat Jun 26 08:45:41 UTC 2021 , Edited by admin on Sat Jun 26 08:45:41 UTC 2021
PRIMARY
FDA UNII
L3KM17324B
Created by admin on Sat Jun 26 08:45:41 UTC 2021 , Edited by admin on Sat Jun 26 08:45:41 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE