ChemicalBook > CAS DataBase List > Fluprednisolone

Fluprednisolone

Product Name
Fluprednisolone
CAS No.
53-34-9
Chemical Name
Fluprednisolone
Synonyms
Alphadrol;U-7800;Etadrol;NSC-47439;fluprednisolone;6α-FLUPREDNISOLONE;6α-Fluprednisolone;6-a-Fluorprednisolone;6a-fluoroprednisolone;6-α-fluoroprednisolone
CBNumber
CB8854834
Molecular Formula
C21H27FO5
Formula Weight
378.43
MOL File
53-34-9.mol
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Fluprednisolone Property

Melting point:
208-213°
alpha 
D +92°
Density 
1.1023 (rough estimate)
refractive index 
1.5980 (estimate)
storage temp. 
Refrigerator
solubility 
Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
color 
White
Water Solubility 
174.2mg/L(20 ºC)
EPA Substance Registry System
Fluprednisolone (53-34-9)
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Safety

WGK Germany 
3
Hazardous Substances Data
53-34-9(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
34206
Product name
6-α-Fluoroprednisolone
Purity
VETRANAL
Packaging
100mg
Price
$720
Updated
2022/05/15
TRC
Product number
F596610
Product name
6α-Fluprednisolone
Packaging
25mg
Price
$1455
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
SHG0005115
Product name
6-ALPHA-FLUPREDINSOLONE
Purity
95.00%
Packaging
50MG
Price
$861.05
Updated
2021/12/16
AK Scientific
Product number
C609
Product name
Fluprednisolone
Packaging
25mg
Price
$268
Updated
2021/12/16
1Pluschem
Product number
1P00DEPD
Product name
Fluprednisolone
Purity
98%(HPLC)
Packaging
25mg
Price
$283
Updated
2021/12/16
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Fluprednisolone Chemical Properties,Usage,Production

Description

Fluprednisolone (6α-fluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione) is the 16-desmethyl analogue of paramethasone. Its activity is similar to that of paramethasone, and it has approximately 2.5 times the antirheumatic potency of prednisolone. With doses of 2 to 7 mg, evidence of salt and water retention has not been noted. The therapeutic index, however, probably is the same or only a little greater than that for prednisolone. Because no new adverse reactions have been noted during the administration of this drug on a short-term basis, it seems that a 6α-fluoro group does not deleteriously affect the activity of prednisolone (49,75).

Originator

Alphadrol, Upjohn ,US,1961

Uses

6α-Fluprednisolone is an anti-inflammatory corticosteroid metabolite.

Uses

Glucocorticoid.

Definition

ChEBI: 6alpha-Fluoroprednisolone is a fluorinated steroid.

Manufacturing Process

5α,11β,17α-Trihydroxy-6β-Fluoro-21-Acetoxyallopregnane-3,20-Dione:A solution of 0.47 gram of 5α,11β,17α-trihydroxy-6β-fluoro-21acetoxyallopregnane-3,20-dione-3-ethylene ketal in 35 ml of acetone and 4 ml of 1 N sulfuric acid solution was gently boiled on the steam bath for 10 minutes, cooled and neutralized with dilute sodium bicarbonate solution. Addition of water and cooling gave 0.33 gram of 5α,11β,17α-trihydroxy-6βfluoro-21-acetoxyallopregnane-3,20-dione, MP 230° to 240°C.
6β-Fluoro-11β,17α-Dihydroxy-21-Acetoxy-4-Pregnene-3,20-Dione(6βFluorohydrocortisone Acetate): A solution of 100 mg of 5α,11β,17α-trihydroxy6β-fluoro-21-acetoxyallopregnane-3,20-dione in 4.9 ml of acetic acid and 0.1 ml of water was refluxed for a period of 1 hour, cooled, diluted with 50 ml of water and evaporated to dryness under reduced pressure. The residue was chromatographed over Florisil (synthetic magnesium silicate) to give one fraction (77 mg) eluted with methylene chloride plus 10% acetone. Crystallization from acetone-Skellysolve B-hexanes gave 38 mg of 6β-fluoro11β,17α-dihydroxy-21-acetoxy-4pregnene-3,20-dione (6β-fluorohydrocortisone6β-Fluoro-11β,17α-Dihydroxy-21-Acetoxy-1,4-Pregnadiene-3,20-Dione: A medium consisting of 1% dextrose hydrate, 2% cornsteep liquor of 60% solids and Kalamazoo tap water was adjusted to pH 4.9 with sodium hydroxide. The medium was steam sterilized at 15 pounds pressure for 30 minutes, cooled, and then inoculated with a 24-hour growth, from spores, of Septomyxa affinis, ATCC 6737. The medium was agitated, sparged with sterile air at the rate of one-tenth volume of air per volume of medium per minute. At the end of 24 hours of fermentation at room temperature, the pH was about 7.4.
To this culture there was added a solution of 6β-fluoro-11β,17α-dihydroxy-21acetoxy-4-pregnene-3,20-dione (6β-fluorohydrocortisone acetate), dissolved in diethylformamide. The solution was prepared by dissolving five parts of the steroid in 100 parts of the solid and adding about 10 cm of the solution per liter of the medium. Fermentation was continued for a period of 48 hours whereupon the mycelium and beer were extracted thoroughly with methylene chloride. The extract was washed with sodium bicarbonate solution and then with water, dried and concentrated in vacuo to a slightly viscous residue. The residue, after reacetylation with acetic anhydride in pyridine, was fractionated chromatographically and 6β-fluoro-11β,17α-dihydroxy-21-acetoxy-1,4pregnadiene-3,20-dione was recovered as a light-colored crystalline solid. Isomerization to the 6β-fluoro product is effected by streaming dry HCl into a cold chloroform/ethanol solution of the 6α-epimer.

brand name

Alphadrol (Pharmacia & Upjohn).

Therapeutic Function

Glucocorticoid, Antiinflammatory

Fluprednisolone Preparation Products And Raw materials

Raw materials

Preparation Products

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53-34-9, FluprednisoloneRelated Search:


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