(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide

• ChemBase编号: 73102
• 分子式: C18H14F4N2O4S
• 平均质量: 430.3733728
• 单一同位素质量: 430.06104082
• SMILES: C(=O)([C@@](CS(=O)(=O)c1ccc(cc1)F)(C)O)Nc1cc(c(cc1)C#N)C(F)(F)F
• Canonical SMILES: N#Cc1ccc(cc1C(F)(F)F)NC(=O)[C@](CS(=O)(=O)c1ccc(cc1)F)(O)C
• InChI: InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)/t17-/m0/s1
• InChIKey: LKJPYSCBVHEWIU-KRWDZBQOSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
• IUPAC传统名: bicalutamide; (2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
• 别名: N-[4-Cyano-3-trifluoromethyl)phenyl]- 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide-d4; ICI-176334-d4; Casodex-d4; Bicalutamide-d4; (R)-Bicalutamide

登记号

• CAS号: 113299-40-4
• PubChem SID: 162038022
• PubChem CID: 56069

理论计算性质

• Acid pKa: 11.947144
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 2.7092955
• LogD (pH = 7.4): 2.7092834
• Log P: 2.7092955
• 摩尔折射率: 96.5895 cm^3
• 极化性: 36.135174 Å^3
• 极化表面积: 107.26 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Dichloromethane
• 外观: White Solid
• 熔点: 192-194°C

安全信息

• 保存条件: -20°C; -20°C Freezer

药理学性质

• 作用靶点: Androgen Receptor

产品相关信息

• 成盐信息: Free Base

详细说明

Selleck Chemicals - S2241

Biological Activity:
(R)-Bicalutamide is an active competitive non-steroidal androgen receptor antagonist with an IC50 of 0.17 μM for MDA 453 cells. (R)-Bicalutamide possesses virtually all activities. (R)-Bicalutamide is the leading antiandrogen. (R)-Bicalutamide is used for the treatment of prostate cancer and breast cancer. (R)-Bicalutamide prevents the activation of the androgen receptor and subsequent upregulation of androgen responsive genes by androgenic hormones. In addition, (R)-bicalutamide accelerates the degradation of the androgen receptor. [1][2][3]References on (R)-Bicalutamide[] PNAS, April 26, 2005, 102:6201–6206[] THE JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277:26321–26326[] J Pharmacol Exp Ther, 2005 February, 312(2): 546–553

Toronto Research Chemicals - B382002

Used as an antiandrogen, antineoplastic (hormonal). (94%d4; 5.7%d3, 0.1%d1, no d0)

参考文献

• Masiello D et al. J Biol Chem. 2002 Jul 19; 277(29):26321-6.
• Tucker, H., et al.: J. Med. Chem., 31, 954 (1988)
• Cockshott, I.D., et al.: Eur. Urol., 18, Suppl. 3, 10 (1988)
• Cockshott, I., et al.: Br. J. Clin. Pharm., 36, 339 (1988)
• McKillop, D., et al.: Xenobiotica, 25, 623 (1988)