This Article Full Text (PDF) Submit a related Letter to the Editor Alert me when this article is cited Alert me when eLetters are posted Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Request Copyright Permission Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by FISHMAN, J. Articles by MARTUCCI, C. Search for Related Content PubMed PubMed Citation Articles by FISHMAN, J. Articles by MARTUCCI, C.

Biological Properties of 16-Hydroxyestrone: Implications in Estrogen Physiology and Pathophysiology^*

The Rockefeller University New York, New York 10021

Address requests for reprints to: Dr. Jack Fishman.The Rockefeller University, 1230 York Avenue, New York, New York 10021.

Metabolism of estradiol in men with cirrhosis and subjects with systemic lupus erythematosus results in an excessive formation of 16±-hydroxyestrone. Examination of the biological activity of this metabolite showed that it is a potent uterotropic agent and that it exhibits minimal affinity for the human sex hormone-binding globulin. These biological characteristics are consistent with a hyperestrongenic response to the substance, which may be reflected in the pathology and etiology of these diseases.

^* This work was supported by Grant CA-22795 from the National Cancer Institute.

Received January 17, 1980.

This article has been cited by other articles:

				A. A. Arslan, R. E. Shore, Y. Afanasyeva, K. L. Koenig, P. Toniolo, and A. Zeleniuch-Jacquotte Circulating Estrogen Metabolites and Risk for Breast Cancer in Premenopausal Women Cancer Epidemiol. Biomarkers Prev., August 1, 2009; 18(8): 2273 - 2279. [Abstract] [Full Text] [PDF]

				B. T. Zhu, G.-Z. Han, J.-Y. Shim, Y. Wen, and X.-R. Jiang Quantitative Structure-Activity Relationship of Various Endogenous Estrogen Metabolites for Human Estrogen Receptor {alpha} and {beta} Subtypes: Insights into the Structural Determinants Favoring a Differential Subtype Binding Endocrinology, September 1, 2006; 147(9): 4132 - 4150. [Abstract] [Full Text] [PDF]

				W. R. Harrington, S. Sengupta, and B. S. Katzenellenbogen Estrogen Regulation of the Glucuronidation Enzyme UGT2B15 in Estrogen Receptor-Positive Breast Cancer Cells Endocrinology, August 1, 2006; 147(8): 3843 - 3850. [Abstract] [Full Text] [PDF]

				A. Wellejus, A. Olsen, A. Tjonneland, B. L. Thomsen, K. Overvad, and S. Loft Urinary Hydroxyestrogens and Breast Cancer Risk among Postmenopausal Women: A Prospective Study Cancer Epidemiol. Biomarkers Prev., September 1, 2005; 14(9): 2137 - 2142. [Abstract] [Full Text] [PDF]

				J. A. Nettleton, K. A. Greany, W. Thomas, K. E. Wangen, H. Adlercreutz, and M. S. Kurzer The Effect of Soy Consumption on the Urinary 2:16-Hydroxyestrone Ratio in Postmenopausal Women Depends on Equol Production Status but Is Not Influenced by Probiotic Consumption J. Nutr., March 1, 2005; 135(3): 603 - 608. [Abstract] [Full Text] [PDF]

				J. S Lewis, T J Thomas, R. G Pestell, C. Albanese, M. A Gallo, and T. Thomas Differential effects of 16{alpha}-hydroxyestrone and 2-methoxyestradiol on cyclin D1 involving the transcription factor ATF-2 in MCF-7 breast cancer cells J. Mol. Endocrinol., February 1, 2005; 34(1): 91 - 105. [Abstract] [Full Text] [PDF]

				C. Atkinson, J. W. Lampe, S. S. Tworoger, C. M. Ulrich, D. Bowen, M. L. Irwin, R. S. Schwartz, B. K. Rajan, Y. Yasui, J. D. Potter, et al. Effects of a Moderate Intensity Exercise Intervention on Estrogen Metabolism in Postmenopausal Women Cancer Epidemiol. Biomarkers Prev., May 1, 2004; 13(5): 868 - 874. [Abstract] [Full Text] [PDF]

				J. D Brooks, W. E Ward, J. E Lewis, J. Hilditch, L. Nickell, E. Wong, and L. U Thompson Supplementation with flaxseed alters estrogen metabolism in postmenopausal women to a greater extent than does supplementation with an equal amount of soy Am. J. Clinical Nutrition, February 1, 2004; 79(2): 318 - 325. [Abstract] [Full Text] [PDF]

				A. J. Lee, A. H. Conney, and B. T. Zhu Human Cytochrome P450 3A7 Has a Distinct High Catalytic Activity for the 16{alpha}-Hydroxylation of Estrone but not 17{beta}-Estradiol Cancer Res., October 1, 2003; 63(19): 6532 - 6536. [Abstract] [Full Text] [PDF]

				E. Riza, I. dos Santos Silva, B. De Stavola, H. L. Bradlow, D. W. Sepkovic, D. Linos, and A. Linos Urinary Estrogen Metabolites and Mammographic Parenchymal Patterns in Postmenopausal Women Cancer Epidemiol. Biomarkers Prev., June 1, 2001; 10(6): 627 - 634. [Abstract] [Full Text] [PDF]

				X. Xu, A. M. Duncan, K. E. Wangen, and M. S. Kurzer Soy Consumption Alters Endogenous Estrogen Metabolism in Postmenopausal Women Cancer Epidemiol. Biomarkers Prev., August 1, 2000; 9(8): 781 - 786. [Abstract] [Full Text]

				C. J. Haggans, E. J. Travelli, W. Thomas, M. C. Martini, and J. L. Slavin The Effect of Flaxseed and Wheat Bran Consumption on Urinary Estrogen Metabolites in Premenopausal Women Cancer Epidemiol. Biomarkers Prev., July 1, 2000; 9(7): 719 - 725. [Abstract] [Full Text]

				L.-J. W. Lu, M. Cree, S. Josyula, M. Nagamani, J. J. Grady, and K. E. Anderson Increased Urinary Excretion of 2-Hydroxyestrone but not 16{{alpha}}-Hydroxyestrone in Premenopausal Women during a Soya Diet Containing Isoflavones Cancer Res., March 1, 2000; 60(5): 1299 - 1305. [Abstract] [Full Text]

				P. T. Mannisto and S. Kaakkola Catechol-O-methyltransferase (COMT): Biochemistry, Molecular Biology, Pharmacology, and Clinical Efficacy of the New Selective COMT Inhibitors Pharmacol. Rev., December 1, 1999; 51(4): 593 - 628. [Abstract] [Full Text] [PDF]

				X. Xu, A. M. Duncan, B. E. Merz-Demlow, W. R. Phipps, and M. S. Kurzer Menstrual Cycle Effects on Urinary Estrogen Metabolites J. Clin. Endocrinol. Metab., November 1, 1999; 84(11): 3914 - 3918. [Abstract] [Full Text]

				C.-S. Huang, H.-D. Chern, K.-J. Chang, C.-W. Cheng, S.-M. Hsu, and C.-Y. Shen Breast Cancer Risk Associated with Genotype Polymorphism of the Estrogen-metabolizing Genes CYP17, CYP1A1, and COMT: A Multigenic Study on Cancer Susceptibility Cancer Res., October 1, 1999; 59(19): 4870 - 4875. [Abstract] [Full Text] [PDF]

				G. Ursin, S. London, F. Z. Stanczyk, E. Gentzschein, A. Paganini-Hill, R. K. Ross, and M. C. Pike Urinary 2-Hydroxyestrone/16{alpha}-Hydroxyestrone Ratio and Risk of Breast Cancer in Postmenopausal Women J Natl Cancer Inst, June 16, 1999; 91(12): 1067 - 1072. [Abstract] [Full Text] [PDF]

				D. Liu and K. A. Bachmann An Investigation of the Relationship Between Estrogen, Estrogen Metabolites and Blood Cholesterol Levels in Ovariectomized Rats J. Pharmacol. Exp. Ther., July 1, 1998; 286(1): 561 - 568. [Abstract] [Full Text]

				R.G. Lahita Sex Steroids and SLE: Metabolism of Androgens to Estrogens Lupus, May 1, 1992; 1(3): 125 - 127. [PDF]