2607-06-9

Basic information

• Product Name: Diflucortolone
• Synonyms: 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
• CAS NO: 2607-06-9
• Molecular Formula: C₂₂H₂₈F₂O₄
• Molecular Weight: 394.45
• EINECS: 220-022-6
• Mol File: 2607-06-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 240-244°; mp 248-249°
• Boiling Point: 534.005 °C at 760 mmHg
• Flash Point: 276.756 °C
• Appearance: /
• Density: 1.295 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly)
• PKA: 12.90±0.70(Predicted)
• CAS DataBase Reference: Diflucortolone(CAS DataBase Reference)
• NIST Chemistry Reference: Diflucortolone(2607-06-9)
• EPA Substance Registry System: Diflucortolone(2607-06-9)

Safety Data

• Hazardous Substances Data: 2607-06-9(Hazardous Substances Data)

Usage

Description

Diflucortolone is a synthetic glucocorticoid, a type of corticosteroid hormone that exhibits potent anti-inflammatory and immunosuppressive properties. It is chemically related to hydrocortisone and is used in the medical field for its therapeutic effects on various conditions.

Uses

Used in Pharmaceutical Industry:
Diflucortolone is used as a glucocorticoid for its anti-inflammatory and immunosuppressive effects, which help in managing inflammation and suppressing the immune system in conditions like allergies, autoimmune disorders, and certain skin conditions.
Used in Dermatology:
Diflucortolone is used as a topical therapy for the treatment of various skin conditions, including eczema, dermatitis, and psoriasis. Its potent anti-inflammatory action helps in reducing redness, itching, and swelling associated with these skin conditions.
Used in Pediatric Dermatology:
Diflucortolone is used as a topical therapy in the treatment of pediatric tinea corporis, a common mycotic infection in children. It helps in reducing inflammation and fighting the fungal infection, leading to improved skin health in affected children.

Originator

Nerisone,Schering,UK,1976

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

InChI:InChI=1/C22H28F2O4/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-21(15,3)22(14,24)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1

Upstream product

• 2135-17-3 flumetasone 
• 4571-51-1 9β,11-epoxy-6α-fluoro-16α-methyl-17,21-dihydroxy-1,4-diene-3,20-dione 21-acetate 
• 23961-95-7 epoxyparamethasone 

Relevant articles and documents

Macrolactonolides: A novel class of anti-inflammatory compounds

A new concept in design of safe glucocorticoid therapy was introduced by conjugating potent glucocorticoid steroids with macrolides (macrolactonolides). These compounds were synthesized from various steroid 17β-carboxylic acids and 9a-N-(3-aminoalkyl) derivatives of 9-deokso-9a-aza-9a-homoeritromicin A and 3-descladinosyl-9-deokso-9a-aza-9a-homoeritromicin A using stable alkyl chain. Combining property of macrolides to preferentially accumulate in immune cells, especially in phagocyte cells, with anti-inflammatory activity of classic steroids, we designed molecules which showed good anti-inflammatory activity in ovalbumin (OVA) induced asthma in rats. The synthesis, in vitro and in vivo anti-inflammatory activity of this novel class of compounds are described.

Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor

Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.