Fluocortolone Property

Melting point:

113-116°C

alpha 

D20 +100° (dioxane)

Boiling point:

537.4±50.0 °C(Predicted)

Density 

1.1001 (estimate)

vapor pressure 

0.001Pa at 25℃

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Dioxane (Slightly), Methanol (Slightly)

form 

Solid

pka

12.98±0.10(Predicted)

color 

Pale Yellow to Yellow

Water Solubility 

204mg/L at 20℃

LogP

2.3 at 25℃

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H360May damage fertility or the unborn child

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

Fluocortolone Chemical Properties,Usage,Production

Chemical Properties

Pale Yellow Solid

Originator

Ultralan,Schering,W. Germany,1965

Uses

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

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