16α-Hydroxyestrone

Source: Wikipedia, the free encyclopedia.
16α-Hydroxyestrone
Names
IUPAC name
3,16α-Dihydroxyestra-1,3,5(10)-trien-17-one
Systematic IUPAC name
(2R,3aS,3bR,9bS,11aS)-2,7-Dihydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
Hydroxyestrone; 16-Hydroxyestrone
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.164.941 Edit this at Wikidata
UNII
  • InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
Properties
C18H22O3
Molar mass 286.371 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

16α-Hydroxyestrone (16α-OH-E1), or hydroxyestrone, also known as estra-1,3,5(10)-triene-3,16α-diol-17-one, is an

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 terms of

antigonadotropic effect of 16α-hydroxyestrone was equivalent to those of estradiol and estriol, indicating that 16α-hydroxyestrone is a fully effective estrogen.[3][8] However, 16α-hydroxyestrone was much less potent than estradiol or estrone.[8]

The C3 and C16α diacetate ester of 16α-hydroxyestrone, hydroxyestrone diacetate (brand names Colpoginon, Colpormon, Hormobion, and Hormocervix), has been marketed and used medically as an estrogen in Europe.[9][10]

Selected biological properties of endogenous estrogens in rats
Estrogen
RBA
Tooltip relative binding affinity (%)		 Uterine weight (%)
Uterotrophy
 LHTooltip Luteinizing hormone levels (%)
RBA
Tooltip 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 =
endogenous
). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

See also

References

  1. ^
    ISBN 978-1-4377-1793-8
    .
  2. ISBN 978-0-08-045978-3
    .
  3. ^
    PMID 7190977
    .
  4. ISBN 978-3-642-58616-3
    .
  5. PMID 3186693
    .
  6. PMID 9472688
    .
  7. S2CID 24616324
    .
  8. ^
    ISBN 9780123955067. {{cite book}}: ISBN / Date incompatibility (help
    )
  9. ISBN 978-3-88763-075-1
    .
  10. ISBN 978-3-7692-2114-5
    .


Retrieved from "https://en.wikipedia.org/w/index.php?title=16α-Hydroxyestrone&oldid=1252492941"