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Details

Stereochemistry ACHIRAL
Molecular Formula C23H25F3N2OS
Molecular Weight 434.5196
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

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

SMILES

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

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
Curator's Comment:: Description was created based on several sources, including https://www.medicines.org.uk/emc/PIL.5400.latest.pdf | http://www.lundbeck.com/upload/au/files/pdf/Fluanxol_CMI.pdf

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLUANXOL

Approved Use

Flupentixol Decanoate Injection and Flupentixol Dihydrochloride Tablets Indication: Schizophrenia and allied psychoses, especially with symptoms such as hallucinations, delusions and thought disturbances along with apathy, lowered mood and withdrawal.
Primary
FLUANXOL

Approved Use

Fluanxol is used to treat depression in patients who may, or may not, also be showing signs of anxiety.
PubMed

PubMed

TitleDatePubMed
[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
Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice.
1982
Abnormal involuntary movements: a study of dopaminergic receptor interaction.
1983
The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria.
1986 Dec
Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists.
1994 Feb 1
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
Effect of flupenthixol on subjective and cardiovascular responses to intravenous cocaine in humans.
2001 Nov 1
Permanent activation of the human P-glycoprotein by covalent modification of a residue in the drug-binding site.
2003 Jun 6
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
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
Patents

Sample Use Guides

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: Other
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 Sat Jun 26 07:22:19 UTC 2021 , Edited by admin on Sat Jun 26 07:22:19 UTC 2021
PRIMARY
FDA UNII
FA0UYH6QUO
Created by admin on Sat Jun 26 07:22:19 UTC 2021 , Edited by admin on Sat Jun 26 07:22:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
258-756-4
Created by admin on Sat Jun 26 07:22:19 UTC 2021 , Edited by admin on Sat Jun 26 07:22:19 UTC 2021
PRIMARY
PUBCHEM
5281881
Created by admin on Sat Jun 26 07:22:19 UTC 2021 , Edited by admin on Sat Jun 26 07:22:19 UTC 2021
PRIMARY
CAS
53772-82-0
Created by admin on Sat Jun 26 07:22:19 UTC 2021 , Edited by admin on Sat Jun 26 07:22:19 UTC 2021
PRIMARY