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Isolation, Characterization, and Synthesis of 3-Ureido-11ß-hydroxy-⁴-androsten-17-one

From the ¹ From the Institute for Steroid Research and the Division of Neoplastic Medicine, Montefiore Hospital and Medical Center, New York, New York 10467

A highly polar metabolite, 3-ureido-11ß-hydroxy-⁴-androsten-17-one (ureasterone), has been isolated from human urine. The structure was derived by infrared, nuclear magnetic resonance, and mass spectrometry, and by degradation of the compound with aqueous acetic acid to 11ß-hydroxy-^3,5-androstadien-17-one and urea. Partial synthesis of the ureidosteroid was achieved by reaction of urea and the allylic alcohol, 3,11ß-dihydroxy-⁴-androsten-17-one, in aqueous solution at pH 5. It was concluded that ureasterone was formed during the incubation of urine at pH 5 to cleave the conjugate of 3,11ß-dihydroxy-⁴-androsten-17-one, a normal metabolite of 11ß-hydroxy-⁴-androstene-3,17-dione.

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