FLUPENTIXOL, (Z)-

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H25F3N2OS
Molecular Weight	434.518
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

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
Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323617702
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: DOI: 10.1016/B978-008055232-3.61770-2	Antagonist 2849
Serotonin 2 (5-HT2) receptor 90 Target ID: CHEMBL2095200 Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323617702	Antagonist 2849
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323617702	Antagonist 2849
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323617702	Antagonist 2849
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323617702	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: http://www.lundbeck.com/upload/au/files/pdf/Fluanxol_CMI.pdf http://www.lundbeck.com/cn/en/products/fluanxol	Primary		Approved 8583	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.
Depression 240 Sources: https://www.medicines.org.uk/emc/PIL.5400.latest.pdf	Primary		Approved 8583	FLUANXOL Approved Use Fluanxol is used to treat depression in patients who may, or may not, also be showing signs of anxiety.

PubMed

Title	Date	PubMed
A comparative trail of fluphenazine decanoate and flupenthixol decanoate.	1975 Feb	1091124
A controlled comparison of flupenthixol and amitriptyline in depressed outpatients.	1976 May 8	773506
Depot injections and tardive dyskinesia.	1978 Oct	709010
Persistent involuntary movements after treatment with flupenthixol.	1981 May 30	6786609
Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice.	1982	6813425
Abnormal involuntary movements: a study of dopaminergic receptor interaction.	1983	6858777
Flupenthixol versus haloperidol in acute psychosis.	1983	6844372
[Pharmacotoxic psychosis and extrapyramidal motor syndrome. A case of acute adverse effect of fluoxetine and flupenthixol].	1992 Sep	1407229
Strain differences in clonidine-induced aggressiveness in mice and its interaction with the dopamine system.	1993 Apr	8097040
Depot flupenthixol-induced mania.	1993 Jun	8211474
Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists.	1994 Feb 1	7905786
Expression and pharmacological characterization of the human D3 dopamine receptor.	1994 Jan	8301582
Convulsions after enflurane in a schizophrenic patient receiving neuroleptics.	1994 May	8055610
High agonist-independent activity is a distinguishing feature of the dopamine D1B receptor subtype.	1994 Nov 11	7525564
Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine.	1995 Sep 5	7498321
Mitochondrial involvement in schizophrenia and other functional psychoses.	1996 Sep	8897462
Tolerability of low dose neuroleptics: a case control study of flupenthixol.	1997 Nov	9443657
Flupenthixol treatment for cocaine abusers with schizophrenia: a pilot study.	1998 Aug	9741939

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: Other

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

.ALPHA.-FLUPENTHIXOL

Preferred 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

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

DTXSID9046310