Spectral analysis and structural identification of a major deflazacort metabolite in man.
1. The structure of a previously reported but uncharacterized major metabolite of deflazacort in man, designated V, 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 (1 beta, 2 beta, 3 beta, 11 beta, 16 beta,)-1,2-epoxy-3,11,21-trihydroxy-2'-methyl-5H'-pregn-4-4-eno [17,16-d]oxazol-20-one.
Huber
E W
EW
Marion Merrell Dow Inc., Analytical and Structural Sciences Department, Cincinnati, OH 45215, USA.
Barbuch
R J
RJ
D000107:Acetylation; D000284:Administration, Oral; D000893:Anti-Inflammatory Agents / Q000652:urine*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D011282:Pregnenediones / Q000652:urine*; D013055:Spectrophotometry, Infrared
D000893:Anti-Inflammatory Agents; D011282:Pregnenediones; C021988:deflazacort