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
SMILES
OCCN1CCN(CC\C=C2\C3=C(SC4=C2C=C(C=C4)C(F)(F)F)C=CC=C3)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-
DescriptionCurator'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
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 |
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Target ID: CHEMBL217 Sources: DOI: 10.1016/B978-008055232-3.61770-2 |
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Target ID: CHEMBL2095200 |
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Target ID: CHEMBL2094251 |
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Target ID: CHEMBL231 |
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Target ID: CHEMBL2094109 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | FLUANXOL Approved UseFlupentixol 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. |
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Primary | FLUANXOL Approved UseFluanxol is used to treat depression in patients who may, or may not, also be showing signs of anxiety. |
PubMed
Title | Date | PubMed |
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Flupenthixol and trifluoperazine: a double-blind investigation in the treatment of schizophrenics. | 1971 Nov |
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A comparative trail of fluphenazine decanoate and flupenthixol decanoate. | 1975 Feb |
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[Allergotoxic brain reaction to flupentixol-depot]. | 1976 Mar-Apr |
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A controlled comparison of flupenthixol and amitriptyline in depressed outpatients. | 1976 May 8 |
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Depot injections and tardive dyskinesia. | 1978 Oct |
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Persistent involuntary movements after treatment with flupenthixol. | 1981 May 30 |
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Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice. | 1982 |
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Abnormal involuntary movements: a study of dopaminergic receptor interaction. | 1983 |
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Flupenthixol versus haloperidol in acute psychosis. | 1983 |
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Neuroleptic malignant syndrome. | 1984 Jun 23 |
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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 |
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The selective dopamine D2 receptor antagonist raclopride discriminates between dopamine-mediated motor functions. | 1986 |
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The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria. | 1986 Dec |
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Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1. | 1991 Apr 18 |
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Strain differences in clonidine-induced aggressiveness in mice and its interaction with the dopamine system. | 1993 Apr |
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Depot flupenthixol-induced mania. | 1993 Jun |
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Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists. | 1994 Feb 1 |
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Expression and pharmacological characterization of the human D3 dopamine receptor. | 1994 Jan |
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Convulsions after enflurane in a schizophrenic patient receiving neuroleptics. | 1994 May |
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High agonist-independent activity is a distinguishing feature of the dopamine D1B receptor subtype. | 1994 Nov 11 |
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Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine. | 1995 Sep 5 |
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Mitochondrial involvement in schizophrenia and other functional psychoses. | 1996 Sep |
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Tolerability of low dose neuroleptics: a case control study of flupenthixol. | 1997 Nov |
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Flupenthixol treatment for cocaine abusers with schizophrenia: a pilot study. | 1998 Aug |
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Effects of flupenthixol and quadazocine on self-administration of speedball combinations of cocaine and heroin by rhesus monkeys. | 1999 Oct |
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Inhibition of HIV replication by neuroleptic agents and their potential use in HIV infected patients with AIDS related dementia. | 2000 Apr |
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Effect of flupenthixol on subjective and cardiovascular responses to intravenous cocaine in humans. | 2001 Nov 1 |
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Association between flupenthixol treatment and emergence of manic symptoms. | 2002 Oct |
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Nonalcoholic steatohepatitis: a possible side effect of atypical antipsychotics. | 2003 Jul |
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Permanent activation of the human P-glycoprotein by covalent modification of a residue in the drug-binding site. | 2003 Jun 6 |
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[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 |
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Post-training intra-striatal scopolamine or flupenthixol impairs radial maze learning in rats. | 2006 Jun 3 |
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Noradrenergic mechanisms in cocaine-induced reinstatement of drug seeking in squirrel monkeys. | 2007 Aug |
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Antitubercular pharmacodynamics of phenothiazines. | 2013 Apr |
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Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes. | 2013 Jun |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26945819
Fupentixol inhibited the proton currents in BV2 microglial cells in a concentration-dependent manner (IC50 6.6 uM).
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SUBSTANCE RECORD