3143. Diflucortolone

Nomenclature

CAS number: 2607-06-9
(6α, 11β, 16α)-6,9-Difluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; 6α,9α-difluoro-16α-methyl-1,4-pregnadiene-11β,21-diol-3,20-dione; 6α,9α-difluoro-16α-methyl-1-dehydrocorticosterone.
C22H28F2O4; mol wt 394.45.
C 66.99%, H 7.15%, F 9.63%, O 16.22%.

Description and references

The 9α-fluoro deriv of fluocortolone, q.v. Prepn: BE 639708; K. Kieslich et al., US 3426128 (1964, 1969, both to Schering AG); eidem, Arzneim.-Forsch. 26, 1462 (1976). Toxicity: P. Gunzel et al., ibid. 1476. Series of articles on pharmacology, toxicity, metabolism and clinical studies: ibid. 26, 1463-1513 (1976).

Chemical structure

Properties

Crystals from ethyl acetate-ether, mp 240-244°. uv max: 237 nm (ε 16600) (Kieslich, 1969). Also reported as mp 248-249°. [α]D22 +111° (methanol) (Kieslich, 1976).

Derivative

21-Valerate.

Nomenclature

CAS number: 59198-70-8
Neribas (Schering AG); Neriforte (Schering AG); Nerisona (Schering AG); Nerisone (Schering AG); Temetex (Sauter); Texmeten (Roche).
C27H36F2O5; mol wt 478.57.
C 67.76%, H 7.58%, F 7.94%, O 16.72%.

Properties

Crystals, mp 195-195.5°. [α]D22 +100.8° (dioxane). Approx LD50 in mice, rats: >4, 3.1 g/kg orally; 180, 13 mg/kg s.c.; 450, 98 mg/kg i.p. (Gunzel).

Therapeutic Category

Anti-inflammatory.

Keywords

Glucocorticoid