Spectral analysis and structural identification of a major deflazacort metabolite in man

Abstract

1. The structure of a previously reported but uncharacterized major metabolite of deflazacort in man, designated V₁, has been characterized by nmr, MS and IR spectral techniques.

2. The major changes in V relative to deflazacort are deacetylation to form the 21-alcohol and A-ring modification to the 1,2-epoxy-3-hydroxy analogue.

3. Based on the spectral data and comparison with model compounds the structure, including relative stereochemistry, is (1β, 2β, 3β, 11β, 16β)-1,2-epoxy-3,11, 21-trihydroxy-2′-methyl-5H′-pregn-4-4-eno[17,16-d]oxazol-20-one.