ChemicalBook >> CAS DataBase List >>Fluprednisolone

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
Molecular Weight:
378.43
MDL Number:
MFCD00200355
MOL File:
53-34-9.mol
Last updated:2023-05-04 17:34:39

Fluprednisolone Properties

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)
FDA UNII 9H05937G3X
EPA Substance Registry System Fluprednisolone (53-34-9)

SAFETY

Risk and Safety Statements

WGK Germany  3

Fluprednisolone price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 34206 6-α-Fluoroprednisolone VETRANAL 53-34-9 100mg $720 2022-05-15 Buy
TRC F596610 6α-Fluprednisolone 53-34-9 25mg $1455 2021-12-16 Buy
American Custom Chemicals Corporation SHG0005115 6-ALPHA-FLUPREDINSOLONE 95.00% 53-34-9 50MG $861.05 2021-12-16 Buy
AK Scientific C609 Fluprednisolone 53-34-9 25mg $268 2021-12-16 Buy
1Pluschem 1P00DEPD Fluprednisolone 98%(HPLC) 53-34-9 25mg $283 2021-12-16 Buy
Product number Packaging Price Buy
34206 100mg $720 Buy
F596610 25mg $1455 Buy
SHG0005115 50MG $861.05 Buy
C609 25mg $268 Buy
1P00DEPD 25mg $283 Buy

Fluprednisolone Chemical Properties,Uses,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

913-49-5
53-34-9
Synthesis of Fluprednisolone from Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

Fluprednisolone Suppliers

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6-a-Fluorprednisolone 6-α-fluoroprednisolone 6ALPHA-FLUPREDINSOLONE,97%MIN 6α-FLUPREDNISOLONE 6a-Fluoro-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 6a-Fluoro-11b,17a,21-trihydroxypregna-1,4-diene-3,20-dione 6α-Fluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione Etadrol NSC-47439 U-7800 (6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one (6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyethanoyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one (6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-17-glycoloyl-11,17-dihydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one fluprednisolone 6a-fluoroprednisolone Fluprednisolone Solution, 100ppm Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6α,11β)- 6alpha-Fluprednisolone Alphadrol Fluprednisolone,methylprednisolone,prednisolone,prednisone,Addison's disease,6α-Fluoroprednisolone,Inhibitor,congenital adrenal virilism,inhibit Methylprednisolone Impurity 28 6α-Fluprednisolone 6-α-Fluoroprednisolone 53-34-9 Alphabetic F FA - FL