113299-40-4

Basic information

• Product Name: (R)-Bicalutamide
• Synonyms: (R)-(-)-BICALUTAMIDE;(R)-BICALUTAMIDE;N-[4-Cyano-3-(Trifluoromethyl)Phenyl]-3-[(4-Flurophenyl)Thio]-2-Hydroxy-2-Methyl-Propanamide;R-BICALUTIMIDE;(R)-Casodex;Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (2R)-;Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (R)-;(2R)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
• CAS NO: 113299-40-4
• Molecular Formula: C₁₈H₁₄F₄N₂O₄S
• Molecular Weight: 430.37
• EINECS: 1806241-263-5
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 113299-40-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 178-181°C
• Boiling Point: 650.3 °C at 760 mmHg
• Flash Point: 347.1 °C
• Appearance: Off-white crystalline solid
• Density: 1.52 g/cm³
• Vapor Pressure: 8.47E-18mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: -20?C Freezer
• Solubility: Acetone (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 11.49±0.29(Predicted)
• CAS DataBase Reference: (R)-Bicalutamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Bicalutamide(113299-40-4)
• EPA Substance Registry System: (R)-Bicalutamide(113299-40-4)

Safety Data

• Hazardous Substances Data: 113299-40-4(Hazardous Substances Data)

Usage

Description

(R)-Bicalutamide, an off-white crystalline solid, is a non-steroidal antiandrogen and antineoplastic agent. It is a chiral molecule with a specific R-configuration, which plays a crucial role in its biological activity and selectivity.

Uses

Used in Pharmaceutical Industry:
(R)-Bicalutamide is used as an antiandrogen for the treatment of prostate cancer. It competitively inhibits androgen receptors, thereby reducing the growth of prostate cancer cells and alleviating symptoms associated with the disease.
(R)-Bicalutamide is also used as an antineoplastic agent, specifically as a hormonal therapy, to control the progression of hormone-sensitive tumors. Its ability to block androgen receptors helps in managing the growth of cancer cells that rely on androgen stimulation for their proliferation.

InChI:InChI=1/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

Upstream product

• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 90357-06-5 Bicalutamide 
• 335595-52-3 (R)-3-(4-fluorophenylmercapto)-2-hydroxy-2-methylpropionic acid 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 371-42-6 4-Fluorothiophenol 
• 928312-15-6 C₁₀H₁₃FO₄S 
• 928312-14-5 C₁₇H₁₉FO₄S 
• 928312-13-4 C₁₇H₁₉FO₂S 
• 890658-79-4 C₁₀H₁₁FO₅S 
• 206193-17-1 (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide 

Downstream Products

• 1226897-60-4 phosphoric acid ester of (R)-bicalutamide 
• 1259485-93-2 O-dibenzyl phosphoric acid ester of (R)-bicalutamide 

Relevant articles and documents

Meta -Non-flat substituents: A novel molecular design to improve aqueous solubility in small molecule drug discovery

Aqueous solubility is a key requirement for small-molecule drug candidates. Here, we investigated the regioisomer-physicochemical property relationships of disubstituted benzenes. We found that meta-isomers bearing non-flat substituents tend to possess the lowest melting point and the highest thermodynamic aqueous solubility among the regioisomers. The examination of pharmaceutical compounds containing a disubstituted benzene moiety supported the idea that the introduction of a non-flat substituent at the meta position of a benzene substructure would be a promising approach for medicinal chemists aiming to improve the thermodynamic aqueous solubility of drug candidates, even though it might not be universally effective. This journal is

Preparation method of (R)-bicalutamide intermediate

The invention relates to a method for preparing an (R)-bicalutamide intermediate. The method comprises the following steps: taking methacrylic acid as a raw material, and obtaining the (R)-bicalutamide intermediate through several steps of esterification, hydroxylation and sulfonation, namely, (R)-3-(4-fluorophenylsulfydryl)-2-hydroxy-2-methylpropionic acid. (R)-bicalutamide with enantioselectivity of more than 99% can be obtained by two simple follow-up reactions of the intermediate. The preparation method has the advantages of easily available starting materials, high reaction yield, easy operation in reaction, high enantioselectivity and wide industrial application prospects.

Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer

Prostate cancer (PC) is one of the major causes of male death worldwide and the development of new and more potent anti-PC compounds is a constant requirement. Among the current treatments, (R)-bicalutamide and enzalutamide are non-steroidal androgen receptor antagonist drugs approved also in the case of castration-resistant forms. Both these drugs present a moderate antiproliferative activity and their use is limited due to the development of resistant mutants of their biological target. Insertion of fluorinated and perfluorinated groups in biologically active compounds is a current trend in medicinal chemistry, applied to improve their efficacy and stability profiles. As a means to obtain such effects, different modifications with perfluoro groups were rationally designed on the bicalutamide and enzalutamide structures, leading to the synthesis of a series of new antiproliferative compounds. Several new analogues displayed improved in vitro activity towards four different prostate cancer cell lines, while maintaining full AR antagonism and therefore representing promising leads for further development. Furthermore, a series of molecular modelling studies were performed on the AR antagonist conformation, providing useful insights on potential protein-ligand interactions.