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Diflucortolone

CAS No.
2607-06-9
Chemical Name:
Diflucortolone
Synonyms
DIFLUCORTOLONE;Difluocortolone;6a,9-difluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione;6α,9-Difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione;Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16-methyl-, (6a,11b,16a)-;Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16-methyl-, (6α,11β,16α)-;(6S,8S,9R,10S,11S,13S,14S,16R,17S)-6,9-difluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one
CBNumber:
CB3219555
Molecular Formula:
C22H28F2O4
Molecular Weight:
394.46
MDL Number:
MFCD00867459
MOL File:
2607-06-9.mol
Last updated:2023-05-04 17:34:36

Diflucortolone Properties

Melting point 240-244°; mp 248-249°
alpha D22 +111° (methanol) (Kieslich, 1976)
Boiling point 534.0±50.0 °C(Predicted)
Density 1.29±0.1 g/cm3(Predicted)
storage temp. -20°C Freezer, Under inert atmosphere
solubility Chloroform (Slightly, Sonicated), DMSO (Slightly)
form Off-White to Pale Grey Soild
pka 12.90±0.70(Predicted)
CAS DataBase Reference 2607-06-9(CAS DataBase Reference)
FDA UNII K253365DXI
ATC code D07AC06,D07XC04

Diflucortolone price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
American Custom Chemicals Corporation HCH0101096 DIFLUCORTOLONE 95.00% 2607-06-9 1G $867.12 2021-12-16 Buy
Medical Isotopes, Inc. 18598 Diflucortolone 2607-06-9 25mg $1190 2021-12-16 Buy
American Custom Chemicals Corporation HCH0101096 DIFLUCORTOLONE 95.00% 2607-06-9 5G $1722.11 2021-12-16 Buy
American Custom Chemicals Corporation HCH0101096 DIFLUCORTOLONE 95.00% 2607-06-9 10G $2771.14 2021-12-16 Buy
AHH MT-50137 Diflucortolone 97% 2607-06-9 5g $350 2021-12-16 Buy
Product number Packaging Price Buy
HCH0101096 1G $867.12 Buy
18598 25mg $1190 Buy
HCH0101096 5G $1722.11 Buy
HCH0101096 10G $2771.14 Buy
MT-50137 5g $350 Buy

Diflucortolone Chemical Properties,Uses,Production

Originator

Nerisone,Schering,UK,1976

Uses

Glucocorticoid. .

Uses

Difluocortolone is used as a topical therapy in the treatment of pediatric tinea corporis; a common mycotic infection in children.

Definition

ChEBI: Diflucortolone is a 21-hydroxy steroid.

Manufacturing Process

16α-Methyl-6α,9α-difluoro-δ4-pregnene-11α,21-diol-3,20-dione-21-acetate (MP = 229°/232°-234°C (with decomposition) is dehydrogenated in 1.2- position by means of Bacillus lentus, Mutant MB 284, whereby the 21-acetate group is simultaneously saponified. (It is possible under the same conditions to start with the free 21-hydroxyl compound.)
For this purpose a fermenter made of stainless steel having a 50 liter capacity is charged with 30 liters of a nutrient solution of 0.1% yeast extract, 0.5% cornsteep and 0.2% glucose, heated for one-half hour at 120°C for sterilization purposes, and after cooling, inoculated with a bacterial suspension of Bacillus lentus MB 284.
After 24 hours of growth at 28°C under stirring (220 revolutions per minute) and aeration (1.65 m3/hr), 1.8 liters of the obtained culture is removed under sterile conditions and transferred with 28 liters of the same sterilized nutrient medium into a fermenter of the same size.
Simultaneously, 6 g of 16α-methyl-6α,9α-difluoro-δ4-pregnene-11β,21-diol3,20-dione-21-acetate in 200 cc of dimethylformamide are added and the fermentation is continued for 50 hours under the same conditions.
The course of the fermentation is tested by removal of samples which are extracted with methyl isobutyl ketone. The extracts are analyzed by thin layer chromatography using a system of benzene/ethyl acetate (4:1).
After further working up there is obtained an oily crystalline residue which is subjected to chromatography on silica gel. The 16α-methyl-6α,9α-difluoroδ1,4-pregnadien-11β,21-diol-3,20-dione is eluated with ethyl acetatechloroform (1:2), it is recrystallized from ethyl acetate/ether and then formed to melt at 240°/242°-244°C. The yield is 60% of the theoretical. The product is reacted with valeric acid chloride to give the valerate ester.

Therapeutic Function

Antiinflammatory

Diflucortolone Preparation Products And Raw materials

Raw materials

Preparation Products

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DIFLUCORTOLONE 6a,9-difluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16-methyl-, (6a,11b,16a)- 6α,9-Difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione (6S,8S,9R,10S,11S,13S,14S,16R,17S)-6,9-difluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one Difluocortolone Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16-methyl-, (6α,11β,16α)- 2607-06-9 2607-6-9 C22H28F2O4