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Details

Stereochemistry ACHIRAL
Molecular Formula C23H25F3N2OS
Molecular Weight 434.518
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUPENTIXOL, (Z)-

SMILES

OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC4=CC=C(C=C24)C(F)(F)F)CC1

InChI

InChIKey=NJMYODHXAKYRHW-DVZOWYKESA-N
InChI=1S/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5-

HIDE SMILES / InChI

Description

Flupenthixol is a thioxanthene antipsychotic used in the treatment of schizophrenia and other psychoses, with the exception of mania and psychomotor hyperactivity due to an activating effect associated with this drug. It may also be employed as an antidepressant. Flupenthixol has a wide range of pharmacological actions. Flupenthixol blocks dopaminergic receptors, thus interfering with dopaminergic transmission in the brain. Flupenthixol also inhibits serotonin 5-HT, histamine H1, muscarinic and alpha-1 adrenergic receptors.

CNS Activity

Originator

PMID

PMID

TitleDatePMID
Flupenthixol and trifluoperazine: a double-blind investigation in the treatment of schizophrenics.
1971 Nov
A comparative trail of fluphenazine decanoate and flupenthixol decanoate.
1975 Feb
[Allergotoxic brain reaction to flupentixol-depot].
1976 Mar-Apr
A controlled comparison of flupenthixol and amitriptyline in depressed outpatients.
1976 May 8
Depot injections and tardive dyskinesia.
1978 Oct
Persistent involuntary movements after treatment with flupenthixol.
1981 May 30
Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice.
1982
Abnormal involuntary movements: a study of dopaminergic receptor interaction.
1983
Flupenthixol versus haloperidol in acute psychosis.
1983
Neuroleptic malignant syndrome.
1984 Jun 23
Pharmacology in vivo of the phenylindan derivative, Lu 19-005, a new potent inhibitor of dopamine, noradrenaline and 5-hydroxytryptamine uptake in rat brain.
1985 Apr
The selective dopamine D2 receptor antagonist raclopride discriminates between dopamine-mediated motor functions.
1986
The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria.
1986 Dec
[D-TRP11]-neurotensin, unlike alpha-flupenthixol, may not block amphetamine-induced hyperactivity in rats.
1989 Mar
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
1991 Apr 18
Effect of selected neuroleptic agents and stereo-isomeric analogues on virus and eukaryotic cells.
1991 May
Positron emission tomographic analysis of central D1 and D2 dopamine receptor occupancy in patients treated with classical neuroleptics and clozapine. Relation to extrapyramidal side effects.
1992 Jul
[Pharmacotoxic psychosis and extrapyramidal motor syndrome. A case of acute adverse effect of fluoxetine and flupenthixol].
1992 Sep
Strain differences in clonidine-induced aggressiveness in mice and its interaction with the dopamine system.
1993 Apr
Depot flupenthixol-induced mania.
1993 Jun
Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists.
1994 Feb 1
Expression and pharmacological characterization of the human D3 dopamine receptor.
1994 Jan
Convulsions after enflurane in a schizophrenic patient receiving neuroleptics.
1994 May
High agonist-independent activity is a distinguishing feature of the dopamine D1B receptor subtype.
1994 Nov 11
Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine.
1995 Sep 5
Mitochondrial involvement in schizophrenia and other functional psychoses.
1996 Sep
Tolerability of low dose neuroleptics: a case control study of flupenthixol.
1997 Nov
Flupenthixol treatment for cocaine abusers with schizophrenia: a pilot study.
1998 Aug
Effects of flupenthixol and quadazocine on self-administration of speedball combinations of cocaine and heroin by rhesus monkeys.
1999 Oct
Inhibition of HIV replication by neuroleptic agents and their potential use in HIV infected patients with AIDS related dementia.
2000 Apr
Effect of flupenthixol on subjective and cardiovascular responses to intravenous cocaine in humans.
2001 Nov 1
Association between flupenthixol treatment and emergence of manic symptoms.
2002 Oct
Nonalcoholic steatohepatitis: a possible side effect of atypical antipsychotics.
2003 Jul
Permanent activation of the human P-glycoprotein by covalent modification of a residue in the drug-binding site.
2003 Jun 6
Direct interactions between the basolateral amygdala and nucleus accumbens core underlie cocaine-seeking behavior by rats.
2004 Aug 11
Encephalopathy and myoclonus triggered by valproic acid.
2004 Sep
[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
Post-training intra-striatal scopolamine or flupenthixol impairs radial maze learning in rats.
2006 Jun 3
Noradrenergic mechanisms in cocaine-induced reinstatement of drug seeking in squirrel monkeys.
2007 Aug
Cell specific dopamine modulation of the transient potassium current in the pyloric network by the canonical D1 receptor signal transduction cascade.
2010 Aug
The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates.
2012 Mar
Antitubercular pharmacodynamics of phenothiazines.
2013 Apr
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes.
2013 Jun
Patent

Sample Use Guides

In Vivo Use Guide
Fluanxol® (flupentixol) 0.5 mg and 1 mg film-coated tablets. The starting dose is usually 1 mg daily taken as a single dose in the morning. This may be increased to 2 mg per day after one week. The maximum daily dose is 3 mg per day. Fluanxol® (flupenthixol decanoate) Depot 20 mg/mL, Concentrated Depot 100 mg/mL. Generally, the starting dose is 20 to 40 mg (1 to 2 mL). A second dose of 20 to 40 mg (1 to 2 mL) is usually given 4-10 days after the first injection, and further doses are given every 2 to 4 weeks for the majority of patients.
Route of Administration: oral, intramuscular
In Vitro Use Guide
Fupentixol inhibited the proton currents in BV2 microglial cells in a concentration-dependent manner (IC50 6.6 uM).
Name Type Language
FLUPENTIXOL, (Z)-
Common Name English
1-PIPERAZINEETHANOL, 4-(3-(2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-, (Z)-
Systematic Name English
4-((3Z)-3-(2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-1-PIPERAZINEETHANOL
Systematic Name English
Z-FLUPENTIXOL
Common Name English
.ALPHA.-FLUPENTHIXOL
Common Name English
Z-FLUPENTHIXOL
Common Name English
ZUFLUPENTIXOL
Common Name English
CIS-FLUPENTHIXOL
Common Name English
CIS-FLUPENTIXOL
Common Name English
1-PIPERAZINEETHANOL, 4-((3Z)-3-(2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
53772-82-0
Created by admin on Tue Mar 06 11:44:57 UTC 2018 , Edited by admin on Tue Mar 06 11:44:57 UTC 2018
PRIMARY
ECHA (EC/EINECS)
258-756-4
Created by admin on Tue Mar 06 11:44:57 UTC 2018 , Edited by admin on Tue Mar 06 11:44:57 UTC 2018
PRIMARY
PUBCHEM
5281881
Created by admin on Tue Mar 06 11:44:57 UTC 2018 , Edited by admin on Tue Mar 06 11:44:57 UTC 2018
PRIMARY SWITZERF
CAS
53772-82-0
Created by admin on Tue Mar 06 11:44:57 UTC 2018 , Edited by admin on Tue Mar 06 11:44:57 UTC 2018
PRIMARY