(1S,2R,10R,11S,15S)-6-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase编号: 72899
• 分子式: C19H26O3
• 平均质量: 302.40794
• 单一同位素质量: 302.18819469
• SMILES: C1C(=O)C(=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C)O
• Canonical SMILES: O=C1CC[C@]2(C(=C1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
• InChIKey: OSVMTWJCGUFAOD-KZQROQTASA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,10R,11S,15S)-6-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione; (1S,2R,10R,11S,15S)-6-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
• IUPAC传统名: formestane
• 别名: 4-Hydroxyandrost-4-ene-3,17-dione, 4-OHA, CGP-32349, Lentaron; 4-Hydroxyandrost-4-ene-3,17-dione; Formestane; 4-Hydroxy-4-androstene-3,17-dione; 4-Androsten-4-ol-3,17-dione; Lentaron(R); 17-dione; CGP-32349; NSC 282175; Formestane

登记号

• CAS号: 566-48-3
• MDL号: MFCD00057814
• PubChem SID: 162037819; 24278220; 24894827
• PubChem CID: 11273

理论计算性质

• Acid pKa: 9.209685
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.4102087
• LogD (pH = 7.4): 3.4036157
• Log P: 3.4102933
• 摩尔折射率: 85.5749 cm^3
• 极化性: 33.33251 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: solid; White Solid
• 熔点: 199-202°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: BV8152500
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 60
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

药理学性质

• 作用靶点: Aromatase
• 相关基因信息: human ... CYP19A1(1588)

产品相关信息

• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C19H26O3

详细说明

Selleck Chemicals - S2208

Research Area: Breast cancer
Biological Activity:
Formestane(Lentaron(R)) is a second generation selective aromatase inhibitor with an IC50 of 80 nM. Formestane(Lentaron(R)) is used in the treatment of estrogen-receptor positive breast cancer in post-menopausal women. Formestane(Lentaron(R)) is often used to suppress estrogen production from anabolic steroids or prohormones. Formestane(Lentaron(R)) also acts as a prohormone to 4-hydroxytestosterone, an active steroid which displays weak androgenic activity in addition to acting as a mild aromatase inhibitor. Formestane has poor oral bioavailability and as such is no longer popular as many orally active aromatase inhibitors have been identified. Cells were treated with different aromatase inhibitors anastrozole, formestane, exemestane, and letrozole, or antiestrogens tamoxifen and fulvestrant. UMB-1Ca cells showed significant growth inhibition in response to fulvestrant (100 nM, P < 0.0005) and partial growth inhibition in response to letrozole (100 nM, P < 0.005). [1][2][3]References on Formestane[3] Ann Oncol., 1994, 5 Suppl 7:S15-7.[1] Cancer Res, 2005, 65:3903-3910[2] Journal of Steroid Biochemistry & Molecular Biology , 2001, 77 :39–47

Sigma Aldrich - F2552

Biochem/physiol Actions
Aromatase inhibitor used as an anti-cancer agent against estrogen-dependent tumors.

Toronto Research Chemicals - F692250

An antitumor drug. An aromatase inhibitor.

参考文献

• L??nning PE et al. J Steroid Biochem Mol Biol. 2001 Apr;77(1):39-47.
• Brodie, A.M. and Njar, V.C.: Steroids, 65, 171 (2000)
• Lonning, P.E., et al.: J. Steroid Biochem, 77, 39 (2001)