Eleven male patients with liver diseases were examined for conjugated estrogens in urines, which were fractionated to the estrogen glucuronides by hydrolysis with β-glucuronidase and estrogen sulfates by solvolysis. Both of them were fractionated further to estrone, estradiol and estriol by modified Brown's method and Salokangas' micromethod. The results were as follows. 1) The ratios of estrogen glucuronides to estrogen sulfates were decreased in all three fractions of estrogen, particularly in estriol in liver diseases, and the extents of decreases of ratios were paralleled with severity of the liver diseases. These decreases came from the relative increases of estrogen sulfates to estrogen glucuronides. 2) Neither levels of estrogen glucuronides and estrogen sulfates in urines, nor ratios of estrogen glucuronides to estrogen sulfates were in distinct correlation with the results of routine liver function tests. 3) The ratios of estrogen glucuronides to estrogen sulfates fluctuated in accordance with the course of the diseases. In convalescence of acute hepatitis, when the results of routine liver function tests had returned to normal ranges, the ratios of estrogen glucuronides to estrogen sulfates were still sometimes decreased, and returned to their normal levels after some delay to the results of other function tests. 4) No distinct correlation between the ratios of estrogen glucuronides to estrogen sulfates and histological findings of liver tissues could be discerned. 5) In a case of Dubin-Johnson's syndrome, the same disordered conjugation and urinary excretion of estrogens were observed as in liver damages.