To install click the Add extension button. That's it.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. You could also do it yourself at any point in time.

How to transfigure the Wikipedia

Would you like Wikipedia to always look as professional and up-to-date? We have created a browser extension. It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology.

Try it — you can delete it anytime.

Install in 5 seconds
4,5
Kelly Slayton
Congratulations on this excellent venture… what a great idea!
Alexander Grigorievskiy
I use WIKI 2 every day and almost forgot how the original Wikipedia looks like.
Live Statistics
English Articles
Improved in 24 Hours
Added in 24 Hours
Languages
Recent
Show all languages
What we do. Every page goes through several hundred of perfecting techniques; in live mode. Quite the same Wikipedia. Just better.
Great Wikipedia has got greater.
.
Leo
Newton
Brights
Milds

16α-Hydroxyestrone

From 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
  • 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 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 terms of relative binding affinity (RBA) for the rat uterine estrogen receptor, 16α-hydroxyestrone showed 2.8% of the affinity of estradiol.[3] For comparison, estrone had 11% of the affinity and estriol had 10% of the affinity of estradiol.[3] In contrast to other estrogens, the binding of 16α-hydroxyestrone to the estrogen receptor is reported to be covalent and irreversible.[4][5][6][7] 16α-Hydroxyestrone has been reported to have 25% of the vaginal estrogenic potency of estradiol.[3] The maximal uterotrophic and 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 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: See template.

YouTube Encyclopedic

  • 1/5
    Views:
    554
    2 494
    646
    59 902
    4 276
  • How to protect your breasts from estrogen
  • High Estrogen Treatment | Lower Your Estrogen Levels NATURALLY!
  • What is DIM and I3C and should you take them for HPV?
  • Does Cruciferous Vegetables Increase or Decrease Estrogen?
  • Седьмой модуль. Андрей Гострый

Transcription

See also

References

  1. ^ a b c Rakel D (2012). Integrative Medicine. Elsevier Health Sciences. pp. 338–339. ISBN 978-1-4377-1793-8.
  2. ^ Vitamins and Hormones. Academic Press. 7 September 2005. pp. 282–. ISBN 978-0-08-045978-3.
  3. ^ a b c d Fishman J, Martucci C (September 1980). "Biological properties of 16 alpha-hydroxyestrone: implications in estrogen physiology and pathophysiology". J. Clin. Endocrinol. Metab. 51 (3): 611–5. doi:10.1210/jcem-51-3-611. PMID 7190977.
  4. ^ 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.
  5. ^ Swaneck GE, Fishman J (November 1988). "Covalent binding of the endogenous estrogen 16 alpha-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intranuclear localization". Proc. Natl. Acad. Sci. U.S.A. 85 (21): 7831–5. Bibcode:1988PNAS...85.7831S. doi:10.1073/pnas.85.21.7831. PMC 282290. PMID 3186693.
  6. ^ Zhu BT, Conney AH (January 1998). "Functional role of estrogen metabolism in target cells: review and perspectives". Carcinogenesis. 19 (1): 1–27. doi:10.1093/carcin/19.1.1. PMID 9472688.
  7. ^ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  8. ^ a b Velardo, Joseph Thomas (1964). "The Actions of Steroid Hormones on Estradiol-17β in Uterine Growth and Enzymorphology". Hormonal Steroids Biochemistry, Pharmacology, and Therapeutics. pp. 463–490. doi:10.1016/B978-0-12-395506-7.50065-0. ISBN 9780123955067.
  9. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1250–. ISBN 978-3-88763-075-1.
  10. ^ 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.



Stub icon

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

Stub icon

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

This page was last edited on 17 September 2023, at 21:35
Basis of this page is in Wikipedia. Text is available under the CC BY-SA 3.0 Unported License. Non-text media are available under their specified licenses. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc. WIKI 2 is an independent company and has no affiliation with Wikimedia Foundation.
Contact WIKI 2
Introduction
Terms of Service
Privacy Policy