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.

Preparation of a novel bridged bis(β-cyclodextrin) chiral stationary phase by thiol-ene click chemistry for enhanced enantioseparation in HPLC

A bridged bis(β-cyclodextrin) ligand was firstly synthesized via a thiol-ene click chemistry reaction between allyl-ureido-β-cyclodextrin and 4-4′-thiobisthiophenol, which was then bonded onto a 5 μm spherical silica gel to obtain a novel bridged bis(β-cyclodextrin) chiral stationary phase (HTCDP). The structures of HTCDP and the bridged bis(β-cyclodextrin) ligand were characterized by the 1H nuclear magnetic resonance (1H NMR), solid state 13C nuclear magnetic resonance (13C NMR) spectra spectrum, scanning electron microscope, elemental analysis, mass spectrometry, infrared spectrometry and thermogravimetric analysis. The performance of HTCDP in enantioseparation was systematically examined by separating 21 chiral compounds, including 8 flavanones, 8 triazole pesticides and 5 other common chiral drugs (benzoin, praziquantel, 1-1′-bi-2-naphthol, Tr?ger's base and bicalutamide) in the reversed-phase chromatographic mode. By optimizing the chromatographic conditions such as formic acid content, mobile phase composition, pH values and column temperature, 19 analytes were completely separated with high resolution (1.50-4.48), in which the enantiomeric resolution of silymarin, 4-hydroxyflavanone, 2-hydroxyflavanone and flavanone were up to 4.34, 4.48, 3.89 and 3.06 within 35 min, respectively. Compared to the native β-CD chiral stationary phase (CDCSP), HTCDP had superior enantiomer separation and chiral recognition abilities. For example, HTCDP completely separated 5 other common chiral drugs, 2 flavanones and 3 triazole pesticides that CDCSP failed to separate. Unlike CDCSP, which has a small cavity (0.65 nm), the two cavities in HTCDP joined by the aryl connector could synergistically accommodate relatively bulky chiral analytes. Thus, HTCDP may have a broader prospect in enantiomeric separation, analysis and detection. This journal is

Catalytic Decarboxylative Radical Sulfonylation

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