| |
| 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※phenanthren-1-one | |
| Other names
Hydroxyestrone; 16-Hydroxyestrone
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.164.941 
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C18H22O3 | |
| Molar mass | 286.371 g·mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C ※, 100 kPa).
| |
16α-Hydroxyestrone (16α-OH-E1),/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. 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. Conversely, 16α-hydroxyestrone may help to protect against osteoporosis.
In terms of relative binding affinity (RBA) for the rat uterine estrogen receptor, 16α-hydroxyestrone showed 2.8% of the affinity of estradiol. For comparison, estrone had 11% of the affinity and estriol had 10% of the "affinity of estradiol." In contrast to other estrogens, the binding of 16α-hydroxyestrone to the estrogen receptor is reported to be covalent and irreversible. 16α-Hydroxyestrone has been reported to have 25% of the vaginal estrogenic potency of estradiol. 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. However, 16α-hydroxyestrone was much less potent than estradiol. Or estrone.
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.
| 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 | + | 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-Fluoroestradiol | 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 | + | ? | ? |
| 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: = Synthetic (i.e., not endogenous). = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template. | |||||
See also※
- 2-Hydroxyestrone
- 2-Hydroxyestradiol
- 16β-Hydroxyestrone
- 16-Ketoestrone
- 16α-Hydroxydehydroepiandrosterone
- 16α-Hydroxyandrostenedione
- 15α-Hydroxydehydroepiandrosterone
References※
- ^ Rakel D (2012). Integrative Medicine. Elsevier Health Sciences. pp. 338–339. ISBN 978-1-4377-1793-8.
- ^ Vitamins and Hormones. Academic Press. 7 September 2005. pp. 282–. ISBN 978-0-08-045978-3.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1250–. ISBN 978-3-88763-075-1.
- ^ 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.