(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one

• ChemBase编号: 4383
• 分子式: C22H27ClO3
• 平均质量: 374.90098
• 单一同位素质量: 374.1648724
• SMILES: ClC1=C[C@@H]2[C@@H]([C@]3([C@@H]4[C@@H](C4)C(=O)C=C13)C)CC[C@]1([C@H]2CC[C@]1(O)C(=O)C)C
• Canonical SMILES: O=C1C=C2C(=C[C@@H]3[C@@H]([C@]2([C@@H]2[C@H]1C2)C)CC[C@]1([C@H]3CC[C@]1(O)C(=O)C)C)Cl
• InChI: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1
• InChIKey: DUSHUSLJJMDGTE-ZJPMUUANSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-6-one; (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0^{2,8}.0^{3,5}.0^{12,16}]octadeca-7,9-dien-6-one
• IUPAC传统名: cyproterone
• 商标名: Androcur; Apo-cyproterone; Gen-Cyproterone; Novo-cyproterone; CyPat
• 别名: Cyproterone acetate; (1β,2β)-6-Chloro-1,2-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; 6-Chloro-6-dehydro-17α-hydroxy-1,2α-methyleneprogesterone; 6-Chloro-17-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione; 1,2α-Methylene-6-chloro-6-17α-hydroxyprogesterone; Cyproterone acetate; Cyproterone

登记号

• CAS号: 2098-66-0
• PubChem SID: 160967815; 46506931
• PubChem CID: 5284537
• CHEBI ID: 50742
• ATC码: G03HA01
• CHEMBL: 142130
• Chemspider ID: 4447594
• DrugBank ID: DB04839
• KEGG ID: D07766
• 美国药典/FDA物质标识码: E61Q31EK2F
• 维基百科标题: Cyproterone_acetate; Cyproterone

理论计算性质

JChem

• Acid pKa: 12.6991005
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.1977315
• LogD (pH = 7.4): 3.1977293
• Log P: 3.1977315
• 摩尔折射率: 102.658 cm^3
• 极化性: 39.728195 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.37
• LOG S: -4.75
• 溶解度: 6.65e-03 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 208-210°C

药理学性质

• 给药途径: oral, intramuscular
• 生物利用度: 100%
• 排泄: 60% bile, 33% renal
• 半衰期: about 40 hours
• 代谢: hepatic
• 蛋白结合率: 96%
• 法定药品分级: Rx-only
• 妊娠期药物分类: X

详细说明

DrugBank - DB04839

• Drug Groups: approved; investigational
• Description: An anti-androgen that, in the form of its acetate (cyproterone acetate), also has progestational properties. It is used in the treatment of hypersexuality in males, as a palliative in prostatic carcinoma, and, in combination with estrogen, for the therapy of severe acne and hirsutism in females. [Pubchem]
• Indication: For the palliative treatment of patients with advanced prostatic carcinoma.
• Pharmacology: Cyproterone is an antiandrogen. It suppresses the actions of testosterone (and its metabolite dihydrotestosterone) on tissues. It acts by blocking androgen receptors which prevents androgens from binding to them and suppresses luteinizing hormone (which in turn reduces testosterone levels).
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. Cyproterone acetate is metabolized by the CYP3A4 enzyme, forming the active metabolite 15beta-hydroxycyproterone acetate, which retains its antiandrogen activity, but has reduced progestational activity.
• Absorption: Completely absorbed following oral administration.
• Half Life: Elimination Following oral or intramuscular administration, the plasma half-life is 38 and 96 hours, respectively.
• Elimination: It is excreted approximately 60% in the bile and 33% through the kidneys.
• References: Giorgi EP, Shirley IM, Grant JK, Stewart JC: Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate. Biochem J. 1973 Mar;132(3):465-74. [Pubmed] ; Pham-Huu-Trung MT, de Smitter N, Bogyo A, Girard F: Effects of cyproterone acetate on adrenal steroidogenesis in vitro. Horm Res. 1984;20(2):108-15. [Pubmed] ; Stadtler FA, Langner V: The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study. Pathol Res Pract. 1985 Mar;179(4-5):493-8. [Pubmed] ; Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, Cornell W, Steele R, Schweitzer R, Schumacher C: Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol Pharmacol. 2003 May;63(5):1012-20. [Pubmed] ; Holdaway IM, Croxson MS, Evans MC, France J, Sheehan A, Wilson T, Ibbertson HK: Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism. Acta Endocrinol (Copenh). 1983 Oct;104(2):222-6. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - C989090

An antiandrogen, suppresses Testosterone and its metabolites. Derivatives of Cyproterone are administered to patients suffering from hypersexuality and to help facilitate the sexual transformation of male-to-female transsexuals.

参考文献

• Giorgi EP, Shirley IM, Grant JK, Stewart JC: Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate. Biochem J. 1973 Mar;132(3):465-74. Pubmed
• Pham-Huu-Trung MT, de Smitter N, Bogyo A, Girard F: Effects of cyproterone acetate on adrenal steroidogenesis in vitro. Horm Res. 1984;20(2):108-15. Pubmed
• Stadtler FA, Langner V: The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study. Pathol Res Pract. 1985 Mar;179(4-5):493-8. Pubmed
• Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, Cornell W, Steele R, Schweitzer R, Schumacher C: Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol Pharmacol. 2003 May;63(5):1012-20. Pubmed
• Holdaway IM, Croxson MS, Evans MC, France J, Sheehan A, Wilson T, Ibbertson HK: Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism. Acta Endocrinol (Copenh). 1983 Oct;104(2):222-6. Pubmed
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