CAS 113299-40-4|(R)-Bicalutamide
Introduction：Basic information about CAS 113299-40-4|(R)-Bicalutamide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | / | Flash Point | 347.1±31.5 °C |
Names
| Name | (R)-Bicalutamide |
|---|---|
| Synonym | More Synonyms |
(R)-Bicalutamide BiologicalActivity
| 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 >>CancerSignaling 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 |
| InChIKey | LKJPYSCBVHEWIU-KRWDZBQOSA-N |
| SMILES | CC(O)(CS(=O)(=O)c1ccc(F)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1 |
| 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 |
