2-(4-{3-[(9Z)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol

• ChemBase ID: 753
• Molecular Formular: C23H25F3N2OS
• Molecular Mass: 434.5176096
• Monoisotopic Mass: 434.16396909
• SMILES: S1c2c(C(=CCCN3CCN(CC3)CCO)c3c1cccc3)cc(cc2)C(F)(F)F
• Canonical SMILES: OCCN1CCN(CC1)CCC=C1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
• InChI: 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
• InChIKey: NJMYODHXAKYRHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{3-[(9Z)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol; 2-(4-{3-[(9E)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol; 2-(4-{3-[2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol
• IUPAC Traditional name: α-flupenthixol; fluanxol; flupenthixol
• Brand Name: Depixol; Emergil; Fluanxol; Fluanxol Depot; Flupentixol; Flurentixol; Fluxanxol; Siplaril; Siplarol
• Synonyms: FX 703; (E/Z)-Flupentixol Dihydrochloride; 4-[3-[(3Z)-2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol Hydrochloride; α-Flupenthixol Hydrochloride; cis-Flupentixol Hydrochloride; Emergil; Fluanxol; Siplarol; Metamin; cis-(Z)-Flupentixol Dihydrochloride; 4-[(3E)-3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol Hydrochloride (1:2); trans-Flupentixol Hydrochloride; 4-[3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol Dihydrochloride; β-Flupenthixol Dihydrochloride; trans-(E)-Flupentixol Dihydrochloride; Flupentixol; Flupenthixole; Flupenthixol

Database IDs

• CAS Number: 2709-56-0; 2413-38-9; 51529-02-3; 51529-01-2
• PubChem SID: 160964216
• PubChem CID: 5281881; 17012
• ATC CODE: N05AF01
• CHEMBL: 42055
• Chemspider ID: 4445173
• DrugBank ID: DB00875
• IUPHAR ligand ID: 948
• KEGG ID: D01044
• Unique Ingredient Identifier: FA0UYH6QUO
• Wikipedia Title: Flupentixol

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.593099
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.669585
• LogD (pH = 7.4): 3.4309251
• Log P: 4.4967875
• Molar Refractivity: 128.1692 cm^3
• Polarizability: 44.335587 Å^3
• Polar Surface Area: 26.71 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.56
• LOG S: -5.04
• Solubility (Water): 3.99e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.000346 mg/ml; Acetone; DMSO; Ethyl Acetate; Methanol
• Apperance: Light Brown Solid; White Solid
• Melting Point: 209-216°C; 223-225°C
• Hydrophobicity(logP): 4.4

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral, IM
• Half Life: 19-39 hours
• Legal Status: Rx-only

DETAILS

DrugBank - DB00875

• Drug Groups: approved
• Description: Flupentixol is an antipsychotic neuroleptic drug. It is a thioxanthene, and therefore closely related to the phenothiazines. Its primary use is as a long acting injection given two or three weekly to people with schizophrenia who have a poor compliance with medication and suffer frequent relapses of illness. It is a D1 and D2 receptor antagonist.
• Indication: For use in the treatment of schizophrenia and depression
• Pharmacology: Flupenthixol is an anxiolytic, antidepressive agent and a mood stabilizer. It inhibits the central monoamine receptors, particularly the dopamine D1 and D2 receptors. Therefore, it increases the amount of serotonin and noradrenaline that control mood and thinking, and improves mood.
• Toxicity: LD₅₀=300 mk/kg (Oral in mice); LD₅₀=791 mg/kg (Oral in rats); LD₅₀=87 mk/kg (IV in mice); LD₅₀=37 mg/kg (IV in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Mainly hepatic
• Absorption: Fairly slow and incomplete after oral administration
• Half Life: 19 to 39 hours
• Protein Binding: Highly bound to plasma proteins (>95%)
• External Links: Wikipedia

Toronto Research Chemicals - F598050

Neuroleptic agent related structurally to thiothixene. Antipsychotic; neuroleptic agent; dopamine receptor antagonist.

Toronto Research Chemicals - F597980

Neuroleptic agent related structurally to thiothixene. Antipsychotic; neuroleptic agent; dopamine receptor antagonist.

Toronto Research Chemicals - F597981

Impurity of cis-(Z)-Flupentixol Dihydrochloride production

REFERENCES

• Nielsen, et al.: Acta Pharmacol. Toxicol., 32, 363 (1973)
• Post, M.L., et al.: Nature, 256, 342 (1973)
• Peuch, et al.: Neuropharmacology, 20, 1279 (1973)
• Nielsen, et al.: Acta Pharmacol. Toxicol., 32, 363 (1973)
• Post, M.L., et al.: Nature, 256, 342 (1973)
• Peuch, et al.: Neuropharmacology, 20, 1279 (1973)
• Li Wan Po, A., et al.: J. Pharm. Pharmacol., 32, 25 (1980)
• Waddington, J., et al.: Eur. J. Pharmacol., 69, 511 (1980)
• Kula, N., et al.: Cell. Mol. Neurobiol., 14, 185 (1980)