4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide

• ChemBase编号: 70492
• 分子式: C21H16F4N4O2S
• 平均质量: 464.4359528
• 单一同位素质量: 464.09300965
• SMILES: C(=O)(c1c(cc(cc1)N1C(=S)N(C(=O)C1(C)C)c1cc(c(cc1)C#N)C(F)(F)F)F)NC
• Canonical SMILES: CNC(=O)c1ccc(cc1F)N1C(=S)N(C(=O)C1(C)C)c1ccc(c(c1)C(F)(F)F)C#N
• InChI: InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)
• InChIKey: WXCXUHSOUPDCQV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide
• IUPAC传统名: 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide
• 别名: 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide; 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl)-2-fluoro-n-methylbenzamide; MDV3100

登记号

• CAS号: 915087-33-1
• MDL号: MFCD14155804
• PubChem SID: 162036208
• PubChem CID: 15951529

理论计算性质

• Acid pKa: 13.054718
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.1554112
• LogD (pH = 7.4): 4.1554103
• Log P: 4.1554112
• 摩尔折射率: 113.4796 cm^3
• 极化性: 41.52869 Å^3
• 极化表面积: 76.44 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 作用靶点: Androgen receptor

产品相关信息

• 纯度: 95+%; 97%
• 成盐信息: Free Base

详细说明

Selleck Chemicals - S1250

Research Area

• Description: Prostate cancer

Protocol

• Protocol: Kinase Assay ^[3]
• AR reporter assay: MDV3100 is evaluated by an artificial AR response reporter system in a hormone refractory prostate cancer cell line. In this system, the prostate cancer LNCaP cells are engineered to stably express about 5-fold higher level of AR than endogenous level. The exogenous AR has similar properties to endogenous AR in that both are stabilized by a synthetic androgen R1881. The AR-over expressed cells are also engineered to stably incorporate an AR response reporter and the reporter activity of these cells shows features of hormone refractory prostate cancer. The antagonistic activity of MDV3100 is tested in the presence of 100 pM of R1881. Engineered LNCaP cells are maintained in Iscove's medium containing 10% fetal bovine serum (FBS). Two days prior to MDV3100 treatment, the cells are grown in Iscove's medium containing 10% charcoal-stripped FBS (CS-FBS) to deprive of androgens. The cells are split and grown in Iscove's medium containing 10% CS-FBS with 100 pM of R1881 and increasing concentrations of MDV3100. After two days of incubation, reporter activities are assayed.
• Protocol: Cell Assay ^[1]
• Cell Lines: LNCaP or LNCaP/AR cells
• Concentrations: 0-10 μM
• Incubation Time: 1-4 days
• Methods: MDV3100 is diluted in DMSO. LNCaP or LNCaP/AR cells (10^4 cells/well) are androgen-starved by growth in media containing 5-10% charcoal-stripped serum for 3-5 days. Then the cells are challenged with various concentrations of MDV3100 in media containing 5-10% charcoal-stripped serum.
• Protocol: Animal Study ^[1]
• Animal Models: Castration-resistant LNCaP/HR xenografts in male SCID mice
• Formulation: Formulated in 1% carboxymethyl cellulose, 0.1% Tween-80, 5% DMSO
• Doses: 10 mg/kg
• Administration: Administered via gavage daily

References

• References: [1] Tran C, et al, Science, 2009, 324 (5928), 787-790.
• References: [2] Scher HI, et al, Lancet, 2010, 375(9724), 1437-1446.
• References: [3] US2007254933 (A1)

参考文献

• Tran C, et al, Science, 2009, 324 (5928), 787-790.
• Scher HI, et al, Lancet, 2010, 375(9724), 1437-1446.
• US2007254933  (A1)