4138. Flumethasone

Nomenclature

CAS number: 2135-17-3
(6α,11β,16α)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 6α,9α-difluoro-16α-methylprednisolone; 6α-fluorodexamethasone; Aniprime (Syntex Diamond); Cortexilar (Veterinaria); Flucort (Syntex); Methagon (Corvel).
C22H28F2O5; mol wt 410.45.
C 64.38%, H 6.88%, F 9.26%, O 19.49%.

Description and references

Prepn: GB 902292; F. H. Lincoln et al., US 3499016 (1962, 1970 both to Upjohn). Prepn of the 21-acetate: J. A. Edwards et al., J. Am. Chem. Soc. 81, 3156 (1959); 82, 2318 (1960).

Chemical structure

Derivative

21-Acetate.
C24H30F2O6; mol wt 452.49.
C 63.70%, H 6.68%, F 8.40%, O 21.22%.

Properties

Crystals from acetone + hexane, mp 260-264°. [α]D +91°. uv max (ethanol): 237 nm (log ε 4.16).

Derivative

21-Pivalate.

Nomenclature

CAS number: 2002-29-1
Locacorten (Novartis); Locorten (Novartis); Lorinden (Polfa).
C27H36F2O6; mol wt 494.57.
C 65.57%, H 7.34%, F 7.68%, O 19.41%.

Therapeutic Category

Glucocorticoid; anti-inflammatory.

Therapeutic Category (Veterinary)

Glucocorticoid.

Keywords

Glucocorticoid