16α-Hydroxyestrone

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16α-Hydroxyestrone
16α-Hydroxyestrone.svg
Names
IUPAC name
(8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Other names
Hydroxyestrone; 16-Hydroxyestrone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.941
Properties
C18H22O3
Molar mass 286.37 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

16α-Hydroxyestrone (16α-OH-E1), or hydroxyestrone, also known as estra-1,3,5(10)-triene-3,16α-diol-17-one, is an endogenous steroidal estrogen and a major metabolite of estrone, as well as an intermediate in the biosynthesis of estriol.[1][2] It is a potent estrogen similarly to estrone, and it has been suggested that the ratio of 16α-hydroxyestrone to 2-hydroxyestrone, the latter being much less estrogenic in comparison and even antiestrogenic in the presence of more potent estrogens like estradiol, may be involved in the pathophysiology of breast cancer.[1] Conversely, 16α-hydroxyestrone may help to protect against osteoporosis.[1] In contrast to estradiol, the binding of 16α-hydroxyestrone to the estrogen receptor is, uniquely, covalent and irreversible, and genotoxicity and aberrant hyperproliferations may result.[3] A diacetate ester of 16α-hydroxyestrone, hydroxyestrone diacetate, has been marketed and is used medically as an estrogen in Europe.[4][5]

See also[edit]

References[edit]

  1. ^ a b c Rakel D (2012). Integrative Medicine. Elsevier Health Sciences. pp. 338–339. ISBN 1-4377-1793-4. 
  2. ^ Vitamins and Hormones. Academic Press. 7 September 2005. pp. 282–. ISBN 978-0-08-045978-3. 
  3. ^ Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 252–. ISBN 978-3-642-58616-3. 
  4. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1250–. ISBN 978-3-88763-075-1. 
  5. ^ Muller NF, Dessing RP, European Society of Clinical Pharmacy (19 June 1998). European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 289–. ISBN 978-3-7692-2114-5.