Anti-Inflammatory Activities of Several 9 α -Halo Derivatives of Adrenal Steroids. ∗

Abstract

Summary

The anti-inflammatory properties of a number of 9 α-halo-11 β-hydroxy steroid derivatives have been compared with some of their halogen-free analogues. The substitution of a fluorine atom at the 9 α-position enhances activity. The presence of various hydroxyl groups in the steroid molecule is essential for maximum anti-inflammatory effect. Hydroxylation at the 17 α-position results in a steroid with increased anti-inflammatory activity. A considerably greater response is demonstrated by the introduction of a 21-hydroxyl group, while maximum activity is achieved by the presence of both 17 α- and 21-hydroxyl groups. The most active compound tested, containing a 9 α-fluorine atom and hydroxyl groups at carbon positions 11 β, 17 α, and 21. was fluoro F acetate. This steroid is approximately 13 times as potent an anti-inflammatory agent as E or F acetate.