17α-Epiestriol

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]

Relative affinities (%) of 17α-epiestriol and related steroids[9][10][11][12]
CompoundPRARERGRMRSHBGCBG
Estradiol2.67.91000.60.138.7<0.1
Alfatradiol<1<115<1<1 ? ?
Estriol<1<115<1<1 ? ?
16β-Epiestriol<1<120<1<1 ? ?
17α-Epiestriol<1<131<1<1 ? ?
Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG.
For other uses, see epiestriol (set index).
17α-Epiestriol
Names
Preferred IUPAC name
(1S,2R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol
Other names
17-Epiestriol; 16α-Hydroxy-17α-estradiol; Estra-1,3,5(10)-triene-3,16α,17α-triol; 3,16α,17α-Trihydroxy-1,3,5(10)-estratriene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
PubChem CID
UNII
InChI
  • InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17-,18+/m1/s1
    Key: PROQIPRRNZUXQM-PNVOZDDCSA-N
SMILES
  • CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
Properties
Chemical formula
 C18H24O3
Molar mass 288.38136 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Tewari AK (5 April 2013). Prostate Cancer: A Comprehensive Perspective. Springer Science & Business Media. pp. 373–. ISBN 978-1-4471-2864-9.
  2. Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 522–. ISBN 978-3-642-96158-8.
  3. Assali NS (3 September 2013). The Maternal Organism. Elsevier. pp. 341–. ISBN 978-1-4832-6380-9.
  4. Von Euler US (2 December 2012). Comparative Endocrinology. Elsevier Science. pp. 135–. ISBN 978-0-323-14609-8.
  5. Tietz NW (1 August 1976). Fundamentals of clinical chemistry. Saunders. p. 773. ISBN 978-0-7216-8866-4.
  6. Sherbet GV (26 July 2013). Therapeutic Strategies in Cancer Biology and Pathology. Elsevier. pp. 83–. ISBN 978-0-12-416590-8.
  7. Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 13–. ISBN 978-1-4832-7299-3.
  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.
  9. 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.
  10. Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Research. 38 (11 Pt 2): 4186–98. PMID 359134.
  11. Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
  12. Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP (January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry. 12: 143–57. doi:10.1016/0022-4731(80)90264-2. PMID 7421203.


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