28416-82-2

Basic information

• Product Name: (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid
• Synonyms: 6a,9a-difluoro-11 P,17a-dihydroxy-16a-methyl-3- oxoandrosta-1,4-diene-17P-carboxylic acid;6α,9α-Difluoro-11β-,17α-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic Acid Discontinued see product # F599490;(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-M;Androsta-1,4-diene-17-carboxylic acid,6,9-difluoro-11,17- dihydroxy-16-Methyl-3-oxo-,(6|á,11|,16|á,17|á)-;(6α,11β,16α,17α)-6,9-Difluoro-11,17-dihydroxy-16-Methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid;6α,9α-Difluoro-11β,17α-dihydroxy-16α-Methylpregna- 3-oxo-1,4-diene-17β-carboxylic Acid;(6A,11B,16A,17A)-6,9-DIFLUORO-11,17-diHYDROXY-16-METHY1-3-OXOANDROSTA-1,4-DIENE-17-CAR;FluMethasone acid
• CAS NO: 28416-82-2
• Molecular Formula: C₂₁H₂₆F₂O₅
• Molecular Weight: 396.42
• EINECS: 206-597-6
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 28416-82-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 303-305°C
• Boiling Point: 568.44oC at 760 mmHg
• Flash Point: 297.582oC
• Appearance: /
• Density: 1.388g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Refrigerator
• Solubility: Acetone (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.49±0.70(Predicted)
• CAS DataBase Reference: (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid(28416-82-2)
• EPA Substance Registry System: (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid(28416-82-2)

Safety Data

• Hazardous Substances Data: 28416-82-2(Hazardous Substances Data)

Usage

Description

(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid, also known as Fluticasone 17β-carboxylic acid, is a white solid intermediate in the synthesis of the glucocorticosteroid Fluticasone propionate. It is a major metabolite of Fluticasone and possesses anti-inflammatory properties.

Uses

Used in Pharmaceutical Industry:
(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid is used as an intermediate in the synthesis of Fluticasone propionate for its anti-inflammatory properties. It plays a crucial role in the development of medications that help reduce inflammation and alleviate symptoms associated with various conditions, such as asthma, allergies, and other inflammatory diseases.
Used in Anti-inflammatory Applications:
(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid is used as an anti-inflammatory agent due to its ability to reduce inflammation and provide relief from various conditions. Its incorporation in pharmaceutical products helps manage symptoms and improve the quality of life for patients suffering from inflammatory disorders.

InChI:InChI=1/C21H26F2O5/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(10,28)17(26)27/h4-5,7,10,12-13,15-16,25,28H,6,8-9H2,1-3H3,(H,26,27)/t10-,12+,13+,15+,16+,18+,19+,20+,21+/m1/s1

Upstream product

• 90566-53-3 fluticasone 
• 2135-17-3 flumetasone 
• 2557-49-5 11β,17α,21-trihydroxy-6α,9α-difluoro-16β-methylpregna-1,4-diene-3,20-dione 
• 2135-17-3 6α,11β,16α-6,9-difluoro-11,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 

Downstream Products

• 105638-31-1 17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene 
• 397864-44-7 fluticasone furoate 
• 1257086-34-2 cyanomethyl (6α,11β,16α,17α)-17-{[4-(3-chloro-4-hydroxyphenoxy)benzoyl]oxy}-6,9-difluoro-11-hydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylate 
• 398455-37-3 6α,9-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-benzoyl-oxyandrosta-1,4-diene-17β-carbothioic acid 
• 80474-45-9 17-propionate carbothioic acid 
• 80486-69-7 S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate 
• 65429-42-7 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid 
• 80474-67-5 S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-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 
• 80473-92-3 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid 
• 73205-13-7 6α,9α-difluoro-11β-hydroxy-17β-<(methylthio)carbonyl>-17α-(propionyloxy)-16α-methylandrosta-1,4-dien-3-one 
• 101916-29-4 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-17β-<(methylthio)carbonyl>-16α-methylandrosta-1,4-dien-3-one 
• 101916-42-1 6α,9α-difluoro-16α,17-dimethyl-11β-hydroxy-18-norandrosta-1,4,13(17)-trien-3-one 

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.

Preparation method of fluticasone propionate intermediate

The invention discloses a preparation method of a fluticasone propionate intermediate. The preparation method comprises the following steps: firstly, preparing silica gel loaded sodium periodate, andthen oxidizing flumetasone by utilizing the silica gel loaded sodium periodate so as to obtain a fluticasone propionate intermediate 6alpha, 9alpha-difluoro-11beta, 17alpha-dyhydroxy-16alpha-methyl-3-oxoandrostane-1, 4-diene-17beta-carboxylic acid. The method has the advantages of readily available reaction raw materials, simple operation, good selectivity, no by-product, stable process, low price, safety, high reaction yield and the like and is beneficial to reduction of the production cost of enterprises and subsequent commercial production and batch supply.

POTENT SOFT ANTI-INFLAMMATORY CORTICOSTEROID COMPOUNDS AND USES THEROF

Potent soft corticosteroid pharmaceutical compositions comprising them and method for use as anti-inflammatory agents. Also, a method for softening fluticasone propionate and similar corticosteroids to arrive at potent but safer alternatives. The compound S-fluoromethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16a- methyl-3-oxoandrosta-1,4-diene-17β-carbothioate, which is equally potent to but safer than fluticasone, is among those provided. Another compound of particular interest is 2-hydroxyethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16β- methyl-3-oxoandrosta-1,4-diene-17β-carboxylate.