Identification of a 6,21-Dihydroxlyated Metabolite of Medroxyprogesterone Acetate in Human Urine

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Abstract
A major metabolite of the orally active progestin, medroxyprogesterone acetate, has been isolated and crystallized from the urine of patients ingesting the compound. Appropriate derivatives of the crystalline metabolite were compared with authentic compounds with respect to chemical reactions (Porter-Silber, BTZ and formaldehyde release); infrared, ultraviolet and sulfuric acid spectra; and mobility in 5 paper chromatographic systems. These comparisons established the metabolite as being 6α-methyl-6β, 17α,21-trihydroxy-4-pregnene-3,20-dione-17-acetate, that is, the 6β,21-dihydroxylated derivative of the parent compound. Both the C-21 and the C-6 hydroxylations were found not to be dependent upon either adrenal or gonadal function or to be influenced appreciably by the presence of the common bacteria of the gut. The major portion of the metabolite was excreted as a conjugate, almost certainly a glucosiduronate, and probably conjugated via the C-21 hydroxyl group. The effects of substitutions at C-6 upon the soda fluorescence reaction, sulfuric acid spectrum and Porter-Silber reaction are discussed.

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