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

• ChemBase编号: 1400
• 分子式: C22H25ClN2OS
• 平均质量: 400.9647
• 单一同位素质量: 400.13761211
• SMILES: Clc1cc2/C(=C\CCN3CCN(CC3)CCO)/c3c(Sc2cc1)cccc3
• Canonical SMILES: OCCN1CCN(CC1)CC/C=C\1/c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-
• InChIKey: WFPIAZLQTJBIFN-DVZOWYKESA-N

名称和登记号

名称

• IUPAC标准名: 2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol
• IUPAC传统名: zuclopenthixol
• 商标名: Clopixol; Acuphase
• 别名: Clopenthixol; Zuclopenthixolum [latin]; Zuclopentixol [spanish]; zuclopenthixol decanoate; zuclopenthixol acetate; zuclopenthixol dihydrochloride; Zuclopenthixol

登记号

• CAS号: 53772-83-1
• PubChem SID: 46507341; 160964860
• PubChem CID: 5311507

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): 1.396457
• LogD (pH = 7.4): 3.1579008
• Log P: 4.222984
• 摩尔折射率: 127.0003 cm^3
• 极化性: 45.285892 Å^3
• 极化表面积: 26.71 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.46
• LOG S: -5.19
• 溶解度: 2.60e-03 g/l

详细说明

DrugBank - DB01624

• Drug Groups: approved
• Description: A thioxanthene with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors. [PubChem]
• Indication: For the management of the manifestations of schizophrenia.
• Pharmacology: Zuclopenthixol is a thioxanthene with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors.
• Toxicity: Although there have not been any cases of overdosage reported, the symptoms are likely to be somnolence, coma, extrapyramidal symptoms, convulsions, hypotension, shock, or hyper- or hypothermia.
• Affected Organisms: Humans and other mammals
• Biotransformation: The metabolism of zuclopenthixol is mainly by sulphoxidation, side chain N-dealkylation and glucuronic acid conjugation. The metabolites are devoid of pharmacological activity.
• Half Life: 20 hours (range 12-28 hours) for the tablet form, 19 days for the depot form.
• Protein Binding: Approximately 98%.
• References: [Link] ; Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. [Pubmed]
• External Links: Wikipedia

参考文献

• Link
• Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. Pubmed