3152. Difluprednate

Nomenclature

CAS number: 23674-86-4
(6α,11β)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione; 6α,9-difluoro-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate; 6α,9α-difluoroprednisolone-21-acetate-17-butyrate; CM-9155; W-6309; Durezol (Sirion); Epitopic (Gerda); Myser (Nikken).
C27H34F2O7; mol wt 508.55.
C 63.77%, H 6.74%, F 7.47%, O 22.02%.

Description and references

Topical corticosteroid. Prepn: A. Ercoli, R. Gardi, ZA 6803686; eidem, US 3780177 (1968, 1973 both to Warner-Lambert); R. Gardi et al., J. Med. Chem. 15, 556 (1972) DOI PubMed. Prepn of ophthalmic formulation: M. Yamaguchi et al., Int. J. Pharm. 301, 121 (2005) DOI PubMed. Anti-inflammatory properties: G. Di Pasquale et al., Steroids 16, 663, 679 (1970) DOI DOI PubMed. HPLC determn in aqueous humor: S.-Yasueda et al., J. Pharm. Biomed. Anal. 30, 1735 (2003) DOI PubMed. Skin penetration and bioavailability study: C. Lafille et al., Dermatologica 159, 277 (1979) PubMed.

Chemical structure

Properties

Crystals from methylene chloride/ether/petr ether, mp 191-194°. [α]D22 +31.7° (c = 0.5 in dioxane). Insol in water. uv max (ethanol): 237-238 nm (E1%1cm 320).

Therapeutic Category

Anti-inflammatory.

Keywords

Glucocorticoid