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

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

Approval Year

PubMed

PubMed

TitleDatePubMed
A controlled comparison of flupenthixol and amitriptyline in depressed outpatients.
1976 May 8
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
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
[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
Patents

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