16α-Hydroxyestrone explained
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. 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.[3] 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.[4] [5] [6] [7] 16α-Hydroxyestrone has been reported to have 25% of the vaginal estrogenic potency of estradiol.[8] 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.[9] 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.[10] [11]
See also
Notes and References
- Book: Rakel, David . vanc . Integrative Medicine. 2012. Elsevier Health Sciences. 978-1-4377-1793-8. 338–339.
- Book: Vitamins and Hormones. 7 September 2005. Academic Press. 978-0-08-045978-3. 282–.
- Fishman J, Martucci C . Biological properties of 16 alpha-hydroxyestrone: implications in estrogen physiology and pathophysiology . J. Clin. Endocrinol. Metab. . 51 . 3 . 611–5 . September 1980 . 7190977 . 10.1210/jcem-51-3-611 .
- Book: Michael . Oettel . Ekkehard . Schillinger . vanc . Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. 6 December 2012. Springer Science & Business Media. 978-3-642-58616-3. 252–.
- Swaneck GE, Fishman J . 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 . November 1988 . 3186693 . 282290 . 10.1073/pnas.85.21.7831 . 1988PNAS...85.7831S . free .
- Zhu BT, Conney AH . Functional role of estrogen metabolism in target cells: review and perspectives . Carcinogenesis . 19 . 1 . 1–27 . January 1998 . 9472688 . 10.1093/carcin/19.1.1 . free .
- Kuhl H . Pharmacology of estrogens and progestogens: influence of different routes of administration . Climacteric . 8 . 3–63 . 2005 . Suppl 1 . 16112947 . 10.1080/13697130500148875 . 24616324 .
- Fishman J, Martucci C . Biological properties of 16 alpha-hydroxyestrone: implications in estrogen physiology and pathophysiology . J. Clin. Endocrinol. Metab. . 51 . 3 . 611–5 . September 1980 . 7190977 . 10.1210/jcem-51-3-611 .
- Book: Velardo. Joseph Thomas. Hormonal Steroids Biochemistry, Pharmacology, and Therapeutics. The Actions of Steroid Hormones on Estradiol-17β in Uterine Growth and Enzymorphology. 1964. 463–490. 10.1016/B978-0-12-395506-7.50065-0. 9780123955067.
- Book: Index Nominum 2000: International Drug Directory. January 2000. Taylor & Francis. 978-3-88763-075-1. 1250–.
- Book: Niels F . Muller . Rudolf P . Dessing . European Society of Clinical Pharmacy . vanc . European Drug Index: European Drug Registrations . Fourth. 19 June 1998. CRC Press. 978-3-7692-2114-5. 289–.