90357-05-4

Basic information

• Product Name: Desfluoro Bicalutamide
• Synonyms: Desfluoro Bicalutamide;(+/-)-N-[4-Cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-3-(phenylsulfonyl)propanaMide;Bicalutamide EP Impurity A;Bicalutamide impurity B
• CAS NO: 90357-05-4
• Molecular Formula: C₁₈H₁₅F₃N₂O₄S
• Molecular Weight: 412.3829096
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 90357-05-4.mol

Chemical Properties

• Melting Point: 175-178 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 656.067°C at 760 mmHg
• Flash Point: 350.577°C
• Appearance: /
• Density: 1.482g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly, Sonicated), Methanol (Sparingly)
• PKA: 11.22±0.29(Predicted)
• CAS DataBase Reference: Desfluoro Bicalutamide(CAS DataBase Reference)
• NIST Chemistry Reference: Desfluoro Bicalutamide(90357-05-4)
• EPA Substance Registry System: Desfluoro Bicalutamide(90357-05-4)

Safety Data

• Hazardous Substances Data: 90357-05-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Desfluoro Bicalutamide is used as a reference standard for quality control and analytical testing in the pharmaceutical industry. It helps ensure the purity and efficacy of Bicalutamide, a nonsteroidal antiandrogen used in the treatment of prostate cancer.
Used in Research and Development:
Desfluoro Bicalutamide serves as a valuable research tool for studying the properties and mechanisms of action of Bicalutamide and other nonsteroidal antiandrogens. It aids in the development of new drugs and therapies for prostate cancer and other related conditions.

InChI:InChI=1/C18H15F3N2O4S/c1-17(25,11-28(26,27)14-5-3-2-4-6-14)16(24)23-13-8-7-12(10-22)15(9-13)18(19,20)21/h2-9,25H,11H2,1H3,(H,23,24)

Upstream product

• 112988-42-8 2-Hydroxy-2-methyl-3-phenylsulfanyl-propionitrile 
• 108-98-5 thiophenol 
• 90357-22-5 α-hydroxy-β-phenylsulfanyl-isobutyric acid 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 90356-00-6 N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[phenylthio]-2-hydroxy-2-methyl-propanamide 

Relevant articles and documents

Synthesis of potential impurities of bicalutamide

Bicalutamide is an oral nonsteroidal, anti-androgen drug used for prostate cancer. It binds to the androgen receptor. During the bulk synthesis of bicalutamide, various impurities are formed. The present work details the development of simple processes for the preparation of impurities of bicalutamide, viz bical-sulfoxides (6), bical-deshydroxy (10), bical-desfluoro (10a), bical-2-fluoro (10b), and bical-3-fluoro (10c). Copyright Taylor & Francis Group, LLC.

Method of treatment for prostatic cancer

Disclosed is a new treatment for men with prostatic cancer involving combination therapy of a 5α-reductase inhibitor, i.e., a 17β-substituted 4-azasteroid, a 17β-substituted non-azasteroid, 17β-acyl-3-carboxyandrost-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylamino-phenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, and particularly finasteride, in combination with an antiandrogen, i.e. flutamide. Pharmaceutical compositions useful for treatment are also disclosed.

Nonsteroidal antiandrogens. Synthesis and structure-activity relationship of 3-substituted derivatives of 2-hydroxypropionanilides

A series of 3-(substituted thio)-2-hydroxypropionanilides and some corresponding sulfones and sulfoxides of general structure 7, in which R' is methyl or trifluoromethyl, were prepared and tested for antiandrogen activity. Members of the trifluoromethyl series (7,R' = CF3) generally exhibited partial androgen agonist activity whereas the members of the methyl series (7,R' = CH3) were pure antagonists. Lead optimization in the methyl series has led to the discovery of novel, potent antiandrogens, which are peripherally selective. One of these, (RS)-4'-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3'-(trifd luoromethyl)propionanilide, 40 (ICI 176334), is being developed currently for the treatment of androgen-responsive benign and malignant disease.

AMIDE DERIVATIVES

Acylanilides of the formula wherein R1 and R2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents; R3 is hydrogen or halogen; R4 is hydrogen or alkyl, or is joined to R5; R5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R4; R6 is alkyl or halogenoalkyl, or has the formula ?A-3-R8 or -A4-X2-A5-R9. A1 and A4, the same or different, each is alkylene; A2, A3 and A5, the same or different, each is a direct link or alkylene; X1 and X2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino; R7 and R9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted; and R8 is phenyl, naphthyl or heterocyclic as defined above for R7 or R9; processes for their manufacture and pharmaceutical compositions containing them. The acylanilides possess antiandrogenic activity