80473-92-3

Basic information

• Product Name: Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6a,11b,16a,17a)-
• Synonyms: Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6a,11b,16a,17a)-;11,17-dihydroxy-16-methyl-3-oxo-,(6α,11β,16α,17α)-;Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-;(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carbothioic acid;6α,9α-Difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17a-carbothioic acid;Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-Methyl-3-oxo-, (6a,11b,16a,1;(6α,11,16α,17α)-;6a,9a-Difluoro-11b,17a-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17b-carbothioic acid
• CAS NO: 80473-92-3
• Molecular Formula: C₂₁H₂₆F₂O₄S
• Molecular Weight: 412.49
• Product Categories: Intermediates & Fine Chemicals;Isotope Labelled compounds;Pharmaceuticals
• Mol File: 80473-92-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 230-231 °C
• Boiling Point: 550.003°C at 760 mmHg
• Flash Point: 286.431°C
• Appearance: /
• Density: 1.364g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: 2-8°C
• PKA: 3.74±0.70(Predicted)
• CAS DataBase Reference: Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6a,11b,16a,17a)-(CAS DataBase Reference)
• NIST Chemistry Reference: Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6a,11b,16a,17a)-(80473-92-3)
• EPA Substance Registry System: Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6a,11b,16a,17a)-(80473-92-3)

Safety Data

• Hazardous Substances Data: 80473-92-3(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C21H26F2O4S/c1-10-6-12-13-8-15(22)14-7-11(24)4-5-18(14,2)20(13,23)16(25)9-19(12,3)21(10,27)17(26)28/h4-5,7,10,12-13,15-16,25,27H,6,8-9H2,1-3H3,(H,26,28)/t10?,12?,13-,15?,16-,18-,19-,20?,21?/m0/s1

Upstream product

• 2135-17-3 flumetasone 
• 709002-84-6 17β-N,N-dimethylthiocarbamoyloxycarbonyl-6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene 
• 28416-82-2 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid 

Downstream Products

• 397864-44-7 fluticasone furoate 
• 80474-45-9 17-propionate carbothioic acid 
• 80474-67-5 S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate 
• 80486-69-7 S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate 
• 80474-24-4 S-fluoromethyl 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate 
• 80474-14-2 flixotide 
• 87556-66-9 C₂₂H₂₇ClF₂O₄S 

Relevant articles and documents

GLUCOCORTICOID RECEPTOR AGONIST AND IMMUNOCONJUGATES THEREOF

Provided herein are glucocorticoid receptor agonist immunoconjugates, glucocorticoid receptor agonists, pharmaceutical compositiosn including the same, and methods of using the same.

Synthesis of substances related to Fluticasone propionate

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Synthesis and structure-activity relationships in a series of antiinflammatory corticosteroid analogues, halomethyl androstane-17β- carbothioates and -17β-carboselenoates

The preparation and topical antiinflammatory potencies of a series of halomethyl 17α-(acyloxy)-11β-hydroxy-3-oxoandrosta-1,4-diene-17β- carbothioates, carrying combinations of 6α-fluoro, 9α-fluoro, 16-methyl, and 16-methylene substituents, are described. Key synthetic stages were the preparation of carbothioic acids and their reaction with dihalomethanes. The carbothioic acids were formed from 17β-carboxylic acids by initial reaction with dimethylthiocarbamoyl chloride followed by aminolysis of the resulting rearranged mixed anhydride with diethylamine, or by carboxyl activation with 1,1'-carbonyldiimidazole (CDI) or 2-fluoro-N-methylpyridinium tosylate (FMPT) and reaction with hydrogen sulfide, the choice of reagent being governed by the 17α-substituent. Carboxyl activation with FMPT and reaction with sodium hydrogen selenide led to the halomethyl 16-methyleneandrostane-17β- carboselenoate analogues. Anti-inflammatory potencies were measured in humans using the vasoconstriction assay and in rats and mice by a modification the Tonelli croton oil ear assay. Best activities were shown by fluoromethyl and chloromethyl carbothioates with a 17α-propionyloxy group. S-Fluoromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta- 1,4-diene-17β-carbothioate (fluticasone propionate, FP) was selected for clinical study as it showed high topical antiinflammatory activity but caused little hypothalamic-pituitary-adrenal suppression after topical or oral administration to rodents.