16-Ketoestrone Explained

16-Ketoestrone (16-keto-E1, or 16-oxoestrone, or 16-oxo-E1) is an endogenous estrogen related to 16α-hydroxyestrone and 16β-hydroxyestrone.[1] [2] [3] In contrast to 16α-hydroxyestrone and 16β-hydroxyestrone, but similarly to 16-ketoestradiol, 16-ketoestrone is a very weak estrogen with less than 1/1000 the estrogenic potency of estrone in the uterus. 16-Ketoestrone has been reported to act as an inhibitor of 17β-hydroxysteroid dehydrogenases.[4] 16-Ketoestrone can be converted by 16α-hydroxysteroid dehydrogenase into estriol in the body.[5]

Notes and References

  1. Breuer. Heinz. The Metabolism of the Natural Estrogens. 20. 1962. 285–335. 0083-6729. Vitamins & Hormones. 10.1016/S0083-6729(08)60720-7. 9780127098203.
  2. Huffman MN, Lott MH . 16-Substituted steroids; 16-keto-alpha-estradiol and 16-ketoestrone . J. Biol. Chem. . 172 . 1 . 325–32 . January 1948 . 10.1016/S0021-9258(18)35637-0 . 18920793 . free .
  3. Huggins C, Jensen EV . The depression of estrone-induced uterine growth by phenolic estrogens with oxygenated functions at positions 6 or 16: the impeded estrogens . J. Exp. Med. . 102 . 3 . 335–46 . September 1955 . 13252187 . 2136510 . 10.1084/jem.102.3.335 .
  4. Inano H, Tamaoki B . Affinity labeling of arginyl residues at the catalytic region of estradiol 17 beta-dehydrogenase from human placenta by 16-oxoestrone . Eur. J. Biochem. . 129 . 3 . 691–5 . January 1983 . 6572146 . 10.1111/j.1432-1033.1983.tb07104.x . free .
  5. Stimmel BF, Grollman A, Huffman MN . The metabolism of 16-ketoestrone and 16-keto-estradiol in man . J. Biol. Chem. . 184 . 2 . 677–85 . June 1950 . 10.1016/S0021-9258(19)51001-8 . 15428451 . free .

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