5174. Isoflupredone

Nomenclature

CAS number: 338-95-4
(11β)-9-Fluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione; 1-dehydro-9α-fluorohydrocortisone; 9-fluoroprednisolone.
C21H27FO5; mol wt 378.43.
C 66.65%, H 7.19%, F 5.02%, O 21.14%.

Description and references

Prepn: J. Fried et al., J. Am. Chem. Soc. 77, 4181 (1955). Microbiological prepn: A. Nobile et al., J. Am. Chem. Soc. 77, 4184 (1955); E. Vischer et al., Helv. Chim. Acta 38, 1502 (1955); T. H. Stoudt et al., Arch. Biochem. Biophys. 59, 304 (1955). Prepn of the 21-acetate: R. F. Hirschmann et al., ibid. 3166; J. A. Hogg et al., ibid. 4438; Ch. Meystre et al., Helv. Chim. Acta 39, 734 (1956); A. Wellstein et al., DE 1020329 (1957 to Ciba), C.A. 54, 25562h (1960); GB 843214 (1960 to Schering), C.A. 55, 5597b (1961). Absorption spectra: L. L. Smith, W. H. Muller, J. Org. Chem. 23, 960 (1958). Mass spectrometry: P. Toft et al., Can. J. Pharm. Sci. 7, 53 (1972). Urinary excretion in horses: D. I. Chapman et al., Vet. Rec. 100, 447 (1977).

Chemical structure

Properties

Crystals from acetone, mp 263-266° (dec). [α]D23 +108° (c = 0.611 in ethanol). uv max (ethanol): 240 nm (ε 15800)(Vischer), also reported as mp 274-275° (dec), [α]D23 +94° (alcohol)(Fried).

Derivative

21-Acetate.

Nomenclature

CAS number: 338-98-7
U-6013; Predef (Pfizer).
C23H29FO6; mol wt 420.47.
C 65.70%, H 6.95%, F 4.52%, O 22.83%.

Properties

Crystals from acetone/isopropyl ether or methanol, mp 244-246° (dec). [α]D23 +108° (c = 0.735 in dioxane). uv max (ethanol): 240 (ε 16250).

Therapeutic Category (Veterinary)

Anti-inflammatory.