Fluocortolone

Chemical properties

Pale Yellow Solid

Originator

Ultralan,Schering,W. Germany,1965

The Uses of Fluocortolone

Fluocortolone is a glucocorticoid used in the treatment of several conditions, including hemorrhoids. Fluocortolone is similar to Fluocortin, but with one less keto group.

What are the applications of Application

Fluocortolone is a glucocorticoid steroid

Background

Fluocortolone is a glucocorticoid with anti-inflammatory activity used topically for various skin disorders.

Definition

ChEBI: Fluocortolone is a 21-hydroxy steroid.

Manufacturing Process

(a) 16α-Methyl-6α-Fluoro-δ4-11β,21-Diol-3,20-Dione:16α-methyl-6α-fluoro-δ4- pregnene-21-ol-3,20-dione-21-acetate (MP 132°/134° to 138°C, UVε238= 15,000) is hydroxylated with Curvularia lunata in 11β-position using the fermentation method whereby the 21-acetate group is simultaneously saponified. The hitherto unknown starting material 16α-methyl-6α-fluoro-δ4- pregnene-21-ol-3,20-dione-21-acetate is obtained from 16α-methyl-δ5- pregnene-3β,21-diol-20-one-21-acetate, MP 152° to 154°C, by the addition of bromofluorine (from N-bromoacetamide and hydrogen fluoride) onto the 5-6 double bond, oxidation of the 3β-hydroxyl group with chromic acid, introduction of the δ4-double bond by splitting of the hydrogen bromide and acid isomerization of the 6β-fluoro substituent to the 16α-methyl-6α-fluoro-δ4- pregnene-21-ol-3,20-dione-21-acetate. By chromatographic purification on silica gel the 16α-methyl-6α-fluoro-δ4-pregnene-11β,21-diol-3,20-dione is: MP 166°/167° to 171°C.
(b) 16α-Methyl-6α-Fluoro-δ4-Pregnene-11β,21-Diol-3,20-Dione-21-Acetate:By reaction of the compound of (a) with acetic anhydride in pyridine at room temperature, the acetate is obtained and recrystallized from ethyl acetate, MP 248°/249° to 251°C.
(c) 16α-Methyl-6α-Fluoro-δ1,4-Pregnadiene-11β,21-Diol-3,20-Dione:16α- methyl-6α-fluoro-δ4-pregnene-11β,21-diol-3,20-dione is dehydrogenated with Corynebacterium simplex. The extraction residue is subjected to chromatography on silica gel and after recrystallization there is obtained from methylene chloride-isopropyl ether 16α-methyl-6α-fluoro-δ1,4-pregnadiene- 11β,21-diol-3,20-dione, MP 180°/181° to 182°C.

Therapeutic Function

Glucocorticoid

Flammability and Explosibility

Not classified

Metabolism

Not Available