Desoximetasone Property

Melting point:

213-215°C

alpha 

D +109° (chloroform)

Boiling point:

532.3±50.0 °C(Predicted)

Density 

376.46

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.98±0.10(Predicted)

form 

Solid

color 

White to Off-White

CAS DataBase Reference

382-67-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-40-43

Safety Statements 

22-26-36

WGK Germany 

3

RTECS 

TU3834000

HS Code 

29147000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

H351Suspected of causing cancer

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Desoximetasone Chemical Properties,Usage,Production

Chemical Properties

Off-White Solid

Originator

Topicorte,Roussel,France,1968

Definition

ChEBI: Dexamethasone in which the hydroxy group at the 17alpha position is substituted by hydrogen. A synthetic corticosteroid with glucocorticoid activity, it is used as an anti-inflammatory and anti-pruritic in the treatment of various skin dis rders, including skin allergies and psoriasis.

Manufacturing Process

(a) Production of 16α-Methyl-4-Pregnene-11β,21-diol-3,20-Dione (= 16αMethylcorticosterone): A fermenter of stainless steel having a 50 liter capacity is charged with 30 liters of a nutrient solution containing:
sterilized for ? hour at 120°C and after cooling, inoculated with a spore suspension of Curvularia lunata which is obtained by rinsing a seven day corn culture (15 grams corn) with approximately 100 cc of physiological sodium chloride solution.
After two days of culturing at 25°C under stirring (220 revolutions per minute) and ventilating (1.65 m3/hr), 18 liters of the obtained culture are removed under sterile conditions and introduced into a fermenter of the same size charged with 28.2 liters of a nutrient solution containing:
After 24 hours cultivation under stirring and ventilation as described above, 7.5 grams of 16α-methyldesoxycorticosterone, obtained by saponification of the corresponding 21-acetate and melting at 102-104°C, in 200 cc of ethanol are added and fermented under the same conditions for 28 hours.
The course of the fermentation is tested by removal of samples, which are extracted with methyl isobutyl ketone. The extract is analyzed by paper chromatography in a system of dioxane + toluene/propylene glycol.
After the end of the fermentation (28 hours) the culture broth is filtered off by suction over a large suction filter. The mycel residue is washed with water several times. The filtrate is extracted three times, each time with 10 liters of methyl isobutyl ketone. The extract is concentrated under vacuum in a circulating evaporator and in a round flask carefully dried under vacuum. The residue is crystallized from acetone/isopropyl ether. The melting point is 157- 158°C (fermentation yield = 60%). The pure product yield obtained after a second crystallization and chromatography of the mother liquor on silica gel amounts to 53% of the theoretical.
(b) 16α-Methyl-9α-Fluoro-?4-Pregnene-11β,21-Diol-3,20-Dione: 7.5 grams of 16α-methyl-9α-fluoro-?4-pregnene-21-ol-3,20-dione-21-acetate, obtained from Step (a) by acetylating with acetic anhydride in pyridine followed by reaction with HF in pyridine at 0°C, are fermented for 36 hours with Curvularia lunata (Mutant NRRL 2380), whereby the 21-acetate group is simultaneously saponified, and then further worked up. The residue is extracted with MIBK, subjected to chromatography on silica gel and there is obtained from chloroform/ethyl acetate (2:1) an eluate containing the 11βhydroxy compound, which is further dehydrogenated as the crude product.
(c) 16α-Methyl-9α-Fluoro-?1,4-Pregnadiene-11β,21-Diol-3,20-Dione: 16αmethyl-9α-fluoro-β4-pregnene-11β,21-diol-3,20-dione obtained as the crude product under Step (b) above, is fermented with Bacillus lentus for 30 hours and further worked up. The residue is extracted with methyl isobutyl ketone and there is obtained as the crude product 16α-methyl-9α-fluoro-?1,4- pregnadiene-11β,21-diol-3,20-dione.

brand name

Topicort (Taro) [Name previously used: Desoxymethasone.].

Therapeutic Function

Antiinflammatory

General Description

Desoximetasone, 9-fluoro-11β, 21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione, like clocortolone pivalate, lacks a C17α OH group inits structure.