Flupentixol

Title: Flupentixol
CAS Registry Number: 2709-56-0
CAS Name: 4-[3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol
Additional Names: 2-trifluoromethyl-9-[3-[4-(b-hydroxyethyl)-1-piperazinyl]propylidene]thioxanthene; flupenthixol
Manufacturers' Codes: N-7009; LC-44
Molecular Formula: C23H25F3N2OS
Molecular Weight: 434.52
Percent Composition: C 63.58%, H 5.80%, F 13.12%, N 6.45%, O 3.68%, S 7.38%
Literature References: Neuroleptic agent related structurally to thiothixene, q.v. Prepn: P. N. Craig, C. L. Zirkle, US 3282930 (1966 to SKF). Prepn of cis- and trans-forms: GB 925538 (1963 to SKF); P. V. Petersen, T. Ammitzboll, US 3681346 (1972 to Kefalas). Metabolism of decanoate: A. Jorgensen et al., Acta Pharmacol. Toxicol. 29, 339 (1971). a-Flupentixol, the cis-isomer, shows greater pharmacological activity than b-flupentixol, the trans-isomer: I. Moller Nielsen et al., Acta Pharmacol. Toxicol. 33, 353 (1973). X-ray crystallography of isomers: M. L. Post et al., Nature 256, 342 (1975).
Derivative Type: Dihydrochloride
CAS Registry Number: 2413-38-9
Trademarks: Emergil (Labaz); Fluanxol (Lundbeck); Siplarol (Erba); Metamin (Takeda)
Molecular Formula: C23H25F3N2OS.2HCl
Molecular Weight: 507.44
Percent Composition: C 54.44%, H 5.36%, F 11.23%, N 5.52%, O 3.15%, S 6.32%, Cl 13.97%
Derivative Type: Decanoate
CAS Registry Number: 30909-51-4
Manufacturers' Codes: Lu-5-110
Trademarks: Depixol (Lundbeck); Fluanxol Dépot (Lundbeck); Viscoleo (Lundbeck)
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Thioxanthenes.
Fluperolone Acetate Fluphenazine Flupirtine Fluprednidene Acetate Fluprednisolone

Flupentixol
Systematic (IUPAC) name
(EZ)-2-[4-[3-[2-(trifluoromethyl)thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol
Clinical data
Trade names Depixol, Fluanxol
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. C
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK)
Rx-only
Routes Oral, IM (including a depot)
Pharmacokinetic data
Bioavailability 40-55% (Oral)[1]
Metabolism Gut wall, hepatic[2]
Half-life 35 hours[1]
Excretion Renal (negligible)[3]
Identifiers
CAS number 2709-56-0 YesY
ATC code N05AF01
PubChem CID 5281881
IUPHAR ligand 968
DrugBank DB00875
ChemSpider 4445173 YesY
UNII FA0UYH6QUO YesY
KEGG D01044 YesY
ChEMBL CHEMBL42055 N
Chemical data
Formula C23H25F3N2OS 
Mol. mass 434.5219 g/mol
 N (what is this?)  (verify)

Flupentixol (INN), also known as flupenthixol (former BAN), marketed under brand names such as Depixol (UK) and Fluanxol (AU, AT, BD, BE, BG, CA, CH, CL, CN, CZ, DE, DK, EE, FI, FR, GE, GR, HK, IE, IL, LT, LV, MT, NL, NO, NZ, OM, PH, PL, PT, RO, RU, SE, SG, SI, SK, TH, TW, UK, ZA) is a typical antipsychotic drug of the thioxanthene class. In addition to single drug preparations, it is also available as Anxiset, Deanxit, Mixit—a combination product containing both melitracen (a tricyclic antidepressant) and flupentixol.

Flupentixol is not approved for use in the US. It is, however, approved for use in the UK,[4] Australia,[5] Canada, South Africa, New Zealand and various other countries.