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Details

Stereochemistry ACHIRAL
Molecular Formula C23H25F3N2OS.2ClH
Molecular Weight 507.439
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

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

SMILES

Cl.Cl.OCCN1CCN(CC\C=C2\C3=C(SC4=C2C=C(C=C4)C(F)(F)F)C=CC=C3)CC1

InChI

InChIKey=IOVDQEIIMOZNNA-MHKBYHAFSA-N
InChI=1S/C23H25F3N2OS.2ClH/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;2*1H/b18-5-;;

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H25F3N2OS
Molecular Weight 434.518
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
A controlled comparison of flupenthixol and amitriptyline in depressed outpatients.
1976 May 8
Persistent involuntary movements after treatment with flupenthixol.
1981 May 30
Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice.
1982
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
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
Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists.
1994 Feb 1
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
Inhibition of HIV replication by neuroleptic agents and their potential use in HIV infected patients with AIDS related dementia.
2000 Apr
[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
Noradrenergic mechanisms in cocaine-induced reinstatement of drug seeking in squirrel monkeys.
2007 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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:52:10 GMT 2023
Edited
by admin
on Fri Dec 15 17:52:10 GMT 2023
Record UNII
96L0Z069N1
Record Status Validated (UNII)
Record Version
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Name Type Language
FLUPENTIXOL DIHYDROCHLORIDE, (Z)-
Common Name English
1-PIPERAZINEETHANOL, 4-((3Z)-3-(2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-, DIHYDROCHLORIDE
Systematic Name English
1-PIPERAZINEETHANOL, 4-(3-((3Z)-2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-, HYDROCHLORIDE (1:2)
Systematic Name English
.ALPHA.-FLUPENTHIXOL HYDROCHLORIDE
Common Name English
1-PIPERAZINEETHANOL, 4-(3-(2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE)PROPYL)-, DIHYDROCHLORIDE, (Z)-
Systematic Name English
CIS-FLUPENTIXOL HYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
51529-01-2
Created by admin on Fri Dec 15 17:52:10 GMT 2023 , Edited by admin on Fri Dec 15 17:52:10 GMT 2023
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PUBCHEM
5282483
Created by admin on Fri Dec 15 17:52:10 GMT 2023 , Edited by admin on Fri Dec 15 17:52:10 GMT 2023
PRIMARY
FDA UNII
96L0Z069N1
Created by admin on Fri Dec 15 17:52:10 GMT 2023 , Edited by admin on Fri Dec 15 17:52:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID501017247
Created by admin on Fri Dec 15 17:52:10 GMT 2023 , Edited by admin on Fri Dec 15 17:52:10 GMT 2023
PRIMARY