17-Epiestriol

17α-Epiestriol

17α-Epiestriol

Chemical compound

For other uses, see epiestriol (set index).

17α-Epiestriol, or simply 17-epiestriol, also known as 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol, is a minor and weak endogenous estrogen, and the 17α-epimer of estriol (which is 16α-hydroxy-17β-estradiol).[1][2][3] It is formed from 16α-hydroxyestrone.[4][5] In contrast to other endogenous estrogens like estradiol, 17α-epiestriol is a selective agonist of the ERβ.[6] It is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα.[7] 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro.[8]

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References

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    Assali NS (3 September 2013). The Maternal Organism. Elsevier. pp. 341–. ISBN 978-1-4832-6380-9.
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    Von Euler US (2 December 2012). Comparative Endocrinology. Elsevier Science. pp. 135–. ISBN 978-0-323-14609-8.
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    Tietz NW (1 August 1976). Fundamentals of clinical chemistry. Saunders. p. 773. ISBN 978-0-7216-8866-4.
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    Sherbet GV (26 July 2013). Therapeutic Strategies in Cancer Biology and Pathology. Elsevier. pp. 83–. ISBN 978-0-12-416590-8.
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    Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 13–. ISBN 978-1-4832-7299-3.
  8. [8]
    Mukherjee TK, Nathan L, Dinh H, Reddy ST, Chaudhuri G (April 2003). "17-epiestriol, an estrogen metabolite, is more potent than estradiol in inhibiting vascular cell adhesion molecule 1 (VCAM-1) mRNA expression". The Journal of Biological Chemistry. 278 (14): 11746–52. doi:10.1074/jbc.M207800200. PMID 12547825.
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    Raynaud, J.P.; Ojasoo, T.; Bouton, M.M.; Philibert, D. (1979). "Receptor Binding as a Tool in the Development of New Bioactive Steroids". Drug Design. pp. 169–214. doi:10.1016/B978-0-12-060308-4.50010-X. ISBN 9780120603084.
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