2-Hydroxyestriol

  1. Home
  2. Wiki
2-Hydroxyestriol
Names
IUPAC name
Estra-1,3,5(10)-triene-2,3,16α,17β-tetrol
Systematic IUPAC name
(1R,2R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7,8-tetrol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H24O4/c1-18-5-4-10-11(13(18)8-16(21)17(18)22)3-2-9-6-14(19)15(20)7-12(9)10/h6-7,10-11,13,16-17,19-22H,2-5,8H2,1H3/t10-,11+,13-,16+,17-,18-/m0/s1
    Key: ZUGCDOZAVASBQT-SLVREZFOSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=CC(=C(C=C34)O)O
Properties
C18H24O4
Molar mass 304.386 g·mol−1
Hazards
GHS labelling:
H351
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Hydroxyestriol, also known as estra-1,3,5(10)-triene-2,3,16α,17β-tetrol, is an endogenous catechol estrogen and metabolite of estriol. It is a suspected carcinogen of carcinogenicity category 2.[1]

Selected biological properties of endogenous estrogens in rats
Estrogen ERTooltip Estrogen receptor RBATooltip relative binding affinity (%) Uterine weight (%) Uterotrophy LHTooltip Luteinizing hormone levels (%) SHBGTooltip Sex hormone-binding globulin RBATooltip relative binding affinity (%)
Control – 100 – 100 –
Estradiol (E2) 100 506 ± 20 +++ 12–19 100
Estrone (E1) 11 ± 8 490 ± 22 +++ ? 20
Estriol (E3) 10 ± 4 468 ± 30 +++ 8–18 3
Estetrol (E4) 0.5 ± 0.2 ? Inactive ? 1
17α-Estradiol 4.2 ± 0.8 ? ? ? ?
2-Hydroxyestradiol 24 ± 7 285 ± 8 +b 31–61 28
2-Methoxyestradiol 0.05 ± 0.04 101 Inactive ? 130
4-Hydroxyestradiol 45 ± 12 ? ? ? ?
4-Methoxyestradiol 1.3 ± 0.2 260 ++ ? 9
4-Fluoroestradiola 180 ± 43 ? +++ ? ?
2-Hydroxyestrone 1.9 ± 0.8 130 ± 9 Inactive 110–142 8
2-Methoxyestrone 0.01 ± 0.00 103 ± 7 Inactive 95–100 120
4-Hydroxyestrone 11 ± 4 351 ++ 21–50 35
4-Methoxyestrone 0.13 ± 0.04 338 ++ 65–92 12
16α-Hydroxyestrone 2.8 ± 1.0 552 ± 42 +++ 7–24 <0.5
2-Hydroxyestriol 0.9 ± 0.3 302 +b ? ?
2-Methoxyestriol 0.01 ± 0.00 ? Inactive ? 4
Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: a = Synthetic (i.e., not endogenous). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: [2][3][4][5][6][7][8][9][10]

See also

[edit]

References

[edit]
  1. ^ "2-HYDROXYESTRIOL". National Center for Biotechnology Information. 17 December 2016. Archived from the original on 26 December 2016. Retrieved 26 December 2016.
  2. ^ Martucci C, Fishman J (March 1976). "Uterine estrogen receptor binding of catecholestrogens and of estetrol (1,3,5(10)-estratriene-3,15alpha,16alpha,17beta-tetrol)". Steroids. 27 (3): 325–333. doi:10.1016/0039-128x(76)90054-4. PMID 178074. S2CID 54412821.
  3. ^ Martucci C, Fishman J (December 1977). "Direction of estradiol metabolism as a control of its hormonal action--uterotrophic activity of estradiol metabolites". Endocrinology. 101 (6): 1709–1715. doi:10.1210/endo-101-6-1709. PMID 590186.
  4. ^ Fishman J, Martucci C (December 1978). "Differential biological activity of estradiol metabolites". Pediatrics. 62 (6 Pt 2): 1128–1133. doi:10.1542/peds.62.6.1128. PMID 724350. S2CID 29609115.
  5. ^ Martucci CP, Fishman J (December 1979). "Impact of continuously administered catechol estrogens on uterine growth and luteinizing hormone secretion". Endocrinology. 105 (6): 1288–1292. doi:10.1210/endo-105-6-1288. PMID 499073.
  6. ^ Fishman J, Martucci CP (1980). "New Concepts of Estrogenic Activity: the Role of Metabolites in the Expression of Hormone Action". In Pasetto N, Paoletti R, Ambrus JL (eds.). The Menopause and Postmenopause. pp. 43–52. doi:10.1007/978-94-011-7230-1_5. ISBN 978-94-011-7232-5.
  7. ^ Fishman J, Martucci C (September 1980). "Biological properties of 16 alpha-hydroxyestrone: implications in estrogen physiology and pathophysiology". The Journal of Clinical Endocrinology and Metabolism. 51 (3): 611–615. doi:10.1210/jcem-51-3-611. PMID 7190977.
  8. ^ Martucci CP (July 1983). "The role of 2-methoxyestrone in estrogen action". Journal of Steroid Biochemistry. 19 (1B): 635–638. doi:10.1016/0022-4731(83)90229-7. PMID 6310247.
  9. ^ Fishman J, Martucci C (1980). "Dissociation of biological activities in metabolites of estradiol". In McLachlan JA (ed.). Estrogens in the Environment: Proceedings of the Symposium on Estrogens in the Environment, Raleigh, North Carolina, U.S.A., September 10-12, 1979. Elsevier. pp. 131–145. ISBN 9780444003720.
  10. ^ Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.



Stub icon

This article about a steroid is a stub. You can help Wikipedia by expanding it.