Etioallocholanol-3(β)-17-One (Isoandrosterone) as a Metabolite of Testosterone in the Human Male. ∗

Abstract

Continuing the study of the metabolic fate of testosterone in the human male, we have now been successful in demonstrating that etioallocholanol-3(β)-17-one (isoandrosterone) is a possible metabolite of testosterone. Previous communications have established androsterone and etiocholanol-3(α)-17-one as metabolic products of testosterone in the human male. 1 , 2 , 3 When testosterone was administered to the adult male guinea pig, etioallocholanol-3(β)-17-one was recovered in the urine. 4

The presence of etioallocholanol-3(β)-17-one has been established in the urine of a patient suffering from adrenal hyperplasia. 5 , 7 Recently, this substance has been isolated from the urine of normal women and also from the urines of both men and women suffering from cancer. 6

The urine was collected from a 30-year-old hypogonadal male during the time the individual was being injected intramuscularly with 30 mg of testosterone propionate† per day. During this period the daily excretion of androgenic substances exceeded 75 International Units (I.U.) per day compared to the value of 14 I.U. per day in the absence of any treatment. A total of 12 days of urine during this treatment was collected.

The urine was extracted in the usual manner and the neutral compounds separated into the ketonic and nonketonic fractions by means of the Girard-Sandulesco reagent. 2

The neutral ketonic compounds were fractionated by means of chromatographic analysis using aluminum oxide (Brockmann) as the absorbent and carbon tetrachloride as the solvent. That fraction which was eluted with carbon tetrachloride containing 0.1% ethanol yielded a crystalline residue on evaporation of the solvent. This crystalline residue was dissolved in 4 cc of hot 90% ethanol, and 170 mg of digitonin in 8 cc of hot 90% ethanol was added.