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

• ChemBase编号: 753
• 分子式: C23H25F3N2OS
• 平均质量: 434.5176096
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: α-flupenthixol; fluanxol; flupenthixol
• 商标名: Depixol; Emergil; Fluanxol; Fluanxol Depot; Flupentixol; Flurentixol; Fluxanxol; Siplaril; Siplarol
• 别名: 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

登记号

• CAS号: 2413-38-9; 51529-01-2; 2709-56-0; 51529-02-3
• PubChem SID: 160964216
• PubChem CID: 17012; 5281881
• ATC码: N05AF01
• CHEMBL: 42055
• Chemspider ID: 4445173
• DrugBank ID: DB00875
• IUPHAR配体索引: 948
• KEGG ID: D01044
• 美国药典/FDA物质标识码: FA0UYH6QUO
• 维基百科标题: Flupentixol

理论计算性质

JChem

• Acid pKa: 15.593099
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.669585
• LogD (pH = 7.4): 3.4309251
• Log P: 4.4967875
• 摩尔折射率: 128.1692 cm^3
• 极化性: 44.335587 Å^3
• 极化表面积: 26.71 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.56
• LOG S: -5.04
• 溶解度: 3.99e-03 g/l

分子性质

理化性质

• 溶解度: 0.000346 mg/ml; Acetone; DMSO; Ethyl Acetate; Methanol
• 外观: Light Brown Solid; White Solid
• 熔点: 209-216°C; 223-225°C
• 疏水性(logP): 4.4

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 给药途径: Oral, IM
• 半衰期: 19-39 hours
• 法定药品分级: Rx-only

详细说明

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

参考文献

• 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)