113299-38-0

Basic information

• Product Name: (S)-BICALUTAMIDE
• Synonyms: (S)-Casodex;Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (2S)-;Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (S)-;(2S)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide;(2S)-N-[3-(Trifluoromethyl)-4-cyanophenyl]-2-methyl-2-hydroxy-3-(4-fluorophenylsulfonyl)propanamide;(S)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide;ICI-187556;BicalutaMide S-IsoMer
• CAS NO: 113299-38-0
• Molecular Formula: C₁₈H₁₄F₄N₂O₄S
• Molecular Weight: 430.37
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 113299-38-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 175-179°C
• Boiling Point: 650.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.52±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• PKA: 11.49±0.29(Predicted)
• CAS DataBase Reference: (S)-BICALUTAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-BICALUTAMIDE(113299-38-0)
• EPA Substance Registry System: (S)-BICALUTAMIDE(113299-38-0)

Safety Data

• Hazardous Substances Data: 113299-38-0(Hazardous Substances Data)

Usage

Description

(S)-BICALUTAMIDE, also known as the (S)-enantiomer of Bicalutamide, is an off-white crystalline solid with antiandrogen and antineoplastic (hormonal) properties. It is a chiral compound that selectively targets androgen receptors, playing a crucial role in the treatment of prostate cancer and other androgen-dependent conditions.
Used in Pharmaceutical Industry:
(S)-BICALUTAMIDE is used as an antiandrogen for the treatment of prostate cancer. It works by blocking the effects of androgens, such as testosterone, which are responsible for the growth and progression of prostate cancer cells. This selective androgen receptor antagonist helps in reducing the size of the tumor and alleviating symptoms associated with advanced prostate cancer.
Additionally, (S)-BICALUTAMIDE is used as a hormonal antineoplastic agent in the treatment of other androgen-dependent conditions. Its ability to inhibit androgen action makes it a valuable therapeutic option for managing hormone-sensitive tumors and related disorders.

Upstream product

• 90357-06-5 Bicalutamide 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 206193-17-1 (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide 
• 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 

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

Separation of racemic bicalutamide by an optimized combination of continuous chromatography and selective crystallization

A racemic mixture of bicalutamide, a drug substance used in the treatment of prostate cancer, was separated by simulated moving bed chromatography, with the objective of maximizing throughput at reduced outlet purity. The enriched extract stream was purified further by a crystallization process exploiting a shift in the eutectic composition. The optimal purity in between both process steps was identified. The separation scheme developed was validated on a scale of 600 g, and the results were compared to those of state-of-the art and discussed. The investigated scheme revealed a wide range of promising coupling conditions while showing superior productivities and enhanced process robustness.

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

Catalytic Decarboxylative Radical Sulfonylation

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