(R)-Bicalutamide

Modify Date: 2024-01-02 10:09:02

(R)-Bicalutamide Structure
(R)-Bicalutamide structure
Common Name (R)-Bicalutamide
CAS Number 113299-40-4 Molecular Weight 430.373
Density 1.5±0.1 g/cm3 Boiling Point 650.3±55.0 °C at 760 mmHg
Molecular Formula C18H14F4N2O4S Melting Point 178-181ºC
MSDS N/A Flash Point 347.1±31.5 °C

 Use of (R)-Bicalutamide


(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].

 Names

Name (R)-Bicalutamide
Synonym More Synonyms

 (R)-Bicalutamide 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
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

 Synonyms

(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
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