906008-94-4

Basic information

• Product Name: Deshydroxy Bicalutamide
• Synonyms: Deshydroxy Bicalutamide;N-[4-Cyano-3-(trifluoroMethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-MethylpropanaMide;BicalutaMide Deshydroxy IMpurity;Bicalutamide EP Impurity C;Bicalutamide impurity D;(RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl) sulfonyl]-2-methyl-propanamide
• CAS NO: 906008-94-4
• Molecular Formula: C₁₈H₁₄F₄N₂O₃S
• Molecular Weight: 414.3739728
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 906008-94-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 154-156 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 612.1°C at 760 mmHg
• Flash Point: 324°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 6.38E-15mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.29±0.70(Predicted)
• CAS DataBase Reference: Deshydroxy Bicalutamide(CAS DataBase Reference)
• NIST Chemistry Reference: Deshydroxy Bicalutamide(906008-94-4)
• EPA Substance Registry System: Deshydroxy Bicalutamide(906008-94-4)

Safety Data

• Hazardous Substances Data: 906008-94-4(Hazardous Substances Data)

Usage

Description

Deshydroxy Bicalutamide, also known as Bicalutamide EP Impurity C, is an intermediate and impurity of Bicalutamide. It is a chemical compound derived from the synthesis process of Bicalutamide, a non-steroidal antiandrogen medication used in the treatment of prostate cancer.

Uses

Used in Pharmaceutical Industry:
Deshydroxy Bicalutamide is used as an intermediate in the synthesis of Bicalutamide, a medication for the treatment of prostate cancer. It plays a crucial role in the production process, ensuring the quality and efficacy of the final product.
Additionally, as an impurity of Bicalutamide, Deshydroxy Bicalutamide is monitored and controlled during the manufacturing process to maintain the safety and purity standards of the medication. This helps in reducing any potential side effects and ensuring the therapeutic benefits of Bicalutamide for patients.

InChI:InChI=1/C18H14F4N2O3S/c1-11(10-28(26,27)15-6-3-13(19)4-7-15)17(25)24-14-5-2-12(9-23)16(8-14)18(20,21)22/h2-8,11H,10H2,1H3,(H,24,25)

Upstream product

• 906008-93-3 N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-methyl-propanamide 
• 90357-53-2 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 

Relevant articles and documents

Discovery of deshydroxy bicalutamide derivatives as androgen receptor antagonists

Deshydroxy propioanilides were synthesised by Michael addition reaction between substituted thiophenols onto four different phenylacrylamide derivatives to give twenty-three novel deshydroxy bicalutamide derivatives lacking the central hydroxyl group. The antiproliferative activities of these compounds were evaluated against human prostate cancer cell lines and thirteen compounds showed better inhibitory activities (IC50 = 2.67–13.19 μM) compared to bicalutamide (IC50 = 20.44 μM) in LNCaP. Remarkably, novel double branched bicalutamide analogues (27 and 28) were isolated as major by-products and found to have the best activity across three human prostate cancer cell lines (LNCaP, VCaP and PC3). The most active compound 28 shows sub-micromolar activity (IC50 = 0.43 μM in LNCaP), which represents more than 40-fold improvement over the clinical anti-androgen bicalutamide (IC50 = 20.44 μM) and a more than 3 fold improvement over enzalutamide (IC50 = 1.36 μM). Moreover, strong reduction of PSA expression in LNCaP cells upon treatment with compounds 27, 28 and 33 was observed during qPCR analysis, confirming their AR antagonist activity. Molecular modelling studies revealed a novel binding mode of these structurally distinct double branched analogues within the ligand binding domain (LBD) of the androgen receptor.