(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

• ChemBase编号: 979
• 分子式: C20H27NO3
• 平均质量: 329.43328
• 单一同位素质量: 329.19909373
• SMILES: O1[C@@]23[C@@]([C@@H]4[C@H]([C@H]5[C@](CC4)([C@@H](O)CC5)C)CC3)(CC(=C(O)[C@@H]12)C#N)C
• Canonical SMILES: N#CC1=C(O)[C@@H]2[C@]3([C@@](C1)(C)[C@H]1CC[C@]4([C@H]([C@@H]1CC3)CC[C@@H]4O)C)O2
• InChI: InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
• InChIKey: KVJXBPDAXMEYOA-CXANFOAXSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile; (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^2,^8.0^6,^8.0^1^2,^1^6]octadec-4-ene-4-carbonitrile
• IUPAC传统名: trilostane
• 商标名: Desopan; Modrastane; Modrenal
• 别名: Trilostane; trilostane; (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile; Win-24540, Desopan, Modrastane, Modrenal; (4α,5α,17β)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile; Trilostane; Vetoryl

登记号

• CAS号: 13647-35-3
• MDL号: MFCD00199295
• PubChem SID: 160964442; 46507062
• PubChem CID: 656583

理论计算性质

JChem

• Acid pKa: 5.2311697
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.8450996
• LogD (pH = 7.4): 0.14754808
• Log P: 2.3007839
• 摩尔折射率: 90.1746 cm^3
• 极化性: 35.464157 Å^3
• 极化表面积: 73.48 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.41
• LOG S: -3.75
• 溶解度: 5.93e-02 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: ≥17 mg/mL; Pyridine
• 外观: Off-White Solid; white to tan powder
• 熔点: 247-257°C (dec.)
• 疏水性(logP): 2.335; 3

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存温度: 2-8°C

药理学性质

• 作用靶点: hydroxysteroid dehydrogenase

产品相关信息

• 纯度: ≥98% (HPLC); 95%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C20H27NO3

详细说明

DrugBank - DB01108

• Drug Groups: approved; withdrawn; investigational
• Description: Trilostane is an inhibitor of 3 beta-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome. It was withdrawn from the United States market in April 1994. [Wikipedia]
• Indication: Used in the treatment of Cushing's syndrome. It is normally used in short-term treatment until permanent therapy is possible.
• Pharmacology: Trilostane blocks an enzyme involved in the production of several steroids including cortisol. Inhibiting this enzyme inhibits the production of cortisol. In Cushing's syndrome, the adrenal gland overproduces steroids. Although steroids are important for various functions of the body, too much can cause problems. Trilostane reduces the amount of steroids produced by the adrenal gland. This product was withdrawn from the U.S. market in April 1994.
• Toxicity: Symptoms of overdose include darkening of skin, drowsiness or tiredness, loss of appetite, mental depression, skin rash, and/or vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 8 hours.
• References: Komanicky P, Spark RF, Melby JC: Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis. J Clin Endocrinol Metab. 1978 Nov;47(5):1042-51. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S1404

Research Area: Endocrinology
Biological Activity:
Trilostane is an inhibitor of 3 β-hydroxysteroid dehydrogenase used in the treatment of Cushing’s syndrome. It is also the first drug approved to treat both pituitary- and adrenal-dependent Cushing’s in dogs. This prescription drug works by stopping the production of cortisol in the adrenal glands. [1]

Sigma Aldrich - SML0141

Biochem/physiol Actions
Trilostane is an inhibitor of 3 β-hydroxysteroid dehydrogenase (3-β-HSD or delta 5-delta 4-isomerase), an essential enzyme for the biosynthesis of all classes of hormonal steroids. It has been used in the treatment of Cushing′s syndrome for stopping the production of cortisol, and is currently approved for dogs in the US, but is still a human drug in the UK and other countries. It is being investigated as a possible treatment for both breast cancer and prostate cancer to prevent the synthesis of estrogens and androgens from endogenous precursors. It has also been used to inhibit endogenous production of progesterone in research studies.

Toronto Research Chemicals - T795600

An inhibitor of steroid biosynthesis. Used as an adrenocortical suppressant. Used in the treatment of breast cancer.

参考文献

• Komanicky P, Spark RF, Melby JC: Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis. J Clin Endocrinol Metab. 1978 Nov;47(5):1042-51. Pubmed
• http://en.wikipedia.org/wiki/Trilostane
• Komanicky, P., et al.: J. Clin. Endocrinol. Metab., 47, 1042 (1978)
• Mori, Y., et al., Chem. Pharm. Bull., 29, 2646 (1978)
• Williams, C.J., et al.: Cancer Treat. Rep., 71, 1197 (1987)