<Suppliers Price>

(R)-Bicalutamide

Names

[ CAS No. ]:
113299-40-4

[ Name ]:
(R)-Bicalutamide

[Synonym ]:
(2R)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (2R)-
(1E,2R)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanimidic acid
R-bicalutamide
Bicalutamide
Propanimidic acid, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (1E,2R)-
R-Bicalutimide
MFCD00870866
Bicalutamide Impurity 2

Biological Activity

[Description]:

(R)-Bicalutamide is the (R)-enantiomer of Bicalutamide (HY-14249). (R)-Bicalutamide is an androgen receptor (AR) antagonist, with antineoplastic activity. (R)-Bicalutamide is widely used for the research of prostate cancer[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Others >> Androgen Receptor

[Target]

AR[1]


[In Vitro]

Bicalutamide (HY-14249) is available as a racemic mixture. The R isomer (R-bicalutamide) has an ≈30-fold higher binding affinity to the AR than the S isomer[1]. (R)-bicalutamide (0.02-20 μM) reduces naïve LNCaP cells survival in a dose-dependent[2]. Cell Proliferation Assay[2] Cell Line: LNCaP cells, LNCaP-Rbic cells Concentration: 0.02 μM, 0.2 μM, 2 μM, 20 μM Incubation Time: 144 hours Result: Reduced naïve LNCaP cells survival in a dose-dependent, with an IC 50 value of about 7μM; exerted a poor antiproliferative effect on LNCaP-Rbic.

[In Vivo]

(R)-Bicalutamide (10 mg/kg; i.g.; daily; for 4 days) has antitumor efficacy in VCaP xenografts mice[3]. Animal Model: CD1 male nude (nu/nu) mice, with VCaP xenografts[3] Dosage: 10 mg/kg Administration: Orally gavage, daily, for 4 consecutive weeks Result: Suppressed tumor growth.

[References]

[1]. Hongli Liu, et al. Molecular mechanism of R-bicalutamide switching from androgen receptor antagonist to agonist induced by amino acid mutations using molecular dynamics simulations and free energy calculation. J Comput Aided Mol Des. 2016 Dec;30(12):1189-1200.

[2]. Sara Pignatta, et al. Prolonged exposure to (R)-bicalutamide generates a LNCaP subclone with alteration of mitochondrial genome. Mol Cell Endocrinol. 2014 Jan 25;382(1):314-324.

[3]. Anna Tesei, et al. Effect of Small Molecules Modulating Androgen Receptor (SARMs) in Human Prostate Cancer Models. PLoS One. 2013; 8(5): e62657.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
650.3±55.0 °C at 760 mmHg

[ Melting Point ]:
178-181ºC

[ Molecular Formula ]:
C18H14F4N2O4S

[ Molecular Weight ]:
430.373

[ Flash Point ]:
347.1±31.5 °C

[ Exact Mass ]:
430.061035

[ PSA ]:
115.64000

[ LogP ]:
4.94

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.578

[ Storage condition ]:
-20?C Freezer

Related Compounds