Description
Fluticasone 17β-carboxylic acid is an intermediate in the synthesis of the glucocorticosteroid fluticasone propionate .
Chemical Properties
White Solid
Uses
The major metabolite of Fluticasone. Anti-inflammatory agent.
Uses
Fluticasone intermediate. Anti-inflammatory agent
General Description
Fluticasone 17β-carboxylic acid ((6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid) is a compound of interest in studying structure-activity relationships within corticosteroid analogs. In research, this compound is examined for its potential interactions with glucocorticoid receptors, given its structural similarity to fluticasone, which is known for its affinity to these receptors. The 17β-carboxylic acid moiety may alter the compound's binding characteristics. In biochemistry, fluticasone 17β-carboxylic acid is used to probe the metabolic pathways of fluticasone, as it may be a metabolite or intermediate.
Synthesis
To a suspension of flumethasone (1.19 g, 2.9 mmol) in tetrahydrofuran (11 ml) was added a solution of periodic acid (2.25 g, 9.9 mmol) in water (5.3 ml). The resulting solution was stirred at RT for 1 h. The tetrahydrofuran was removed in vacuo to leave an aqueous suspension which was filtered, and the solid washed with water and dried to give 1.17 g (100%) of the (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid (Fluticasone 17β-Carboxylic Acid) as a colorless solid.
