Isoflupredone
Title: Isoflupredone
CAS Registry Number: 338-95-4
CAS Name: (11b)-9-Fluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione
Additional Names: 1-dehydro-9a-fluorohydrocortisone; 9-fluoroprednisolone
Molecular Formula: C21H27FO5
Molecular Weight: 378.43
Percent Composition: C 66.65%, H 7.19%, F 5.02%, O 21.14%
Literature 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).
Properties: Crystals from acetone, mp 263-266° (dec). [a]D23 +108° (c = 0.611 in ethanol). uv max (ethanol): 240 nm (e 15800) (Vischer), also reported as mp 274-275° (dec), [a]D23 +94° (alcohol)(Fried).
Melting point: mp 263-266° (dec); mp 274-275° (dec)
Optical Rotation: [a]D23 +108° (c = 0.611 in ethanol); [a]D23 +94° (alcohol)(Fried)
Absorption maximum: uv max (ethanol): 240 nm (e 15800) (Vischer)
 
Derivative Type: 21-Acetate
CAS Registry Number: 338-98-7
Manufacturers' Codes: U-6013
Trademarks: Predef (Pfizer)
Molecular Formula: C23H29FO6
Molecular Weight: 420.47
Percent Composition: C 65.70%, H 6.95%, F 4.52%, O 22.83%
Properties: Crystals from acetone/isopropyl ether or methanol, mp 244-246° (dec). [a]D23 +108° (c = 0.735 in dioxane). uv max (ethanol): 240 (e 16250).
Melting point: mp 244-246° (dec)
Optical Rotation: [a]D23 +108° (c = 0.735 in dioxane)
Absorption maximum: uv max (ethanol): 240 (e 16250)
 
Therap-Cat-Vet: Anti-inflammatory.

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