(1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl acetate

• ChemBase编号: 72619
• 分子式: C24H32O4
• 平均质量: 384.50848
• 单一同位素质量: 384.2300595
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C=C2C)[C@H]2[C@](CC1)([C@](CC2)(C(=O)C)OC(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C)C
• InChI: InChI=1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1
• InChIKey: RQZAXGRLVPAYTJ-GQFGMJRRSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl acetate; (1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC传统名: DMAP
• 别名: 17α-乙酰氧基-6-甲基孕甾-4,6-二烯-3,20-二酮; 17α-羟基-6-甲基-6-去氢孕酮 17-乙酸酯; 17α-羟基-6-甲基孕甾-4,6-二烯-3,20-二酮 17-乙酸酯; 甲地孕酮 17-乙酸酯; 甲地孕酮乙酸酯; Megestrol acetate; 17-(Acetyloxy)-6-methypregna-4,6-diene-3,20-dione; BDH 1298; DMAP; MGA; Magestin; Maygace; Megeron; Megestat; Magestryl Acetate; Ovarid; Megace; Megace ES; Megestrol Acetate; BDH-1298, NSC-71423; 17α-Acetoxy-6-methyl-4,6-pregnadiene-3,20-dione; 17α-Hydroxy-6-methyl-4,6-pregnadiene-3,20-dione 17-acetate; 17α-Hydroxy-6-methyl-6-dehydroprogesterone 17-acetate; Megestrol 17-acetate

登记号

• CAS号: 595-33-5; 3562-63-8
• EC号: 209-864-5
• MDL号: MFCD00056470
• Beilstein号: 1917291
• PubChem SID: 24896559; 162037544; 24870151
• PubChem CID: 11683
• ATC码: G03AC05
• Chemspider ID: 11192
• DrugBank ID: DB00351
• 维基百科标题: Megestrol_acetate

理论计算性质

• Acid pKa: 17.826162
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 3.7237444
• LogD (pH = 7.4): 3.7237444
• Log P: 3.7237444
• 摩尔折射率: 108.6554 cm^3
• 极化性: 42.444622 Å^3
• 极化表面积: 60.44 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 210-212°C

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: TU4075000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40-48
• 安全公开号: 22-24/25
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351-H373
• GHS警示性声明: P281
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: Androgen receptor
• 给药途径: Oral
• 生物利用度: 100% (oral)
• 半衰期: 13 to 105 hours (mean 34 hours)
• 蛋白结合率: Yes (to albumin, but not to sex hormone-binding globulin or transcortin)
• 法定药品分级: Rx-only
• 妊娠期药物分类: X (US)

产品相关信息

• 纯度: ≥99% (HPLC)
• 级别: analytical standard, for drug analysis; VETRANAL™, analytical standard
• 成盐信息: Acetate
• Empirical Formula (Hill Notation): C24H32O4

详细说明

Selleck Chemicals - S1304

Research Area: Cancer
Biological Activity:
Megestrol Acetate is a synthetic progesteronal agent with an IC50 of 260 μM for the inhibition of HegG2. It inhibits the growth of HepG2 cells in vitro in dose- and time-dependent manners. Megestrol is a progesterone derivative with antineoplastic properties used in the treatment of advanced carcinoma of the breast and endometrium. When given in relatively high doses, Megestrol can substantially increase appetite in most individuals, even those with advanced cancer. It is also used to boost appetite in individuals with other cancers or HIV/AIDS. [1][2][3]References on Megestrol Acetate[] Clin Cancer Res, 2004, 10:5226-5232

Sigma Aldrich - 46420

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M208050

Orally active progestogen; formerly used in combinations as oral contraceptive.

参考文献

• http://en.wikipedia.org/wiki/Megestrol
• Chang, K., et al.: Steroids 12, 689 (1968)