Chemistry:Estradiol decanoate
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| Other names | E2D; Estradiol decylate; Estradiol 17β-decanoate; Estra-1,3,5(10)-triene-3,17β-diol 17β-decanoate |
| Routes of administration | By mouth[1][2] |
| Drug class | Estrogen; Estrogen ester |
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| Formula | C28H42O3 |
| Molar mass | 426.641 g·mol−1 |
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Estradiol decanoate (E2D), or estradiol decylate, also known as estradiol 17β-decanoate, is a synthetic steroidal estrogen and an estrogen ester – specifically, the 17β-decanoate (decylate) ester of estradiol – which was studied for use in hormone replacement therapy for ovariectomized women in the late 1970s but was never marketed.[1][2][3]
Oral estradiol decanoate in oil at a dosage of 0.25 to 0.5 mg/day for 14 days has been studied in ovariectomized women and found to produce levels of estrone and estradiol with a ratio of about 1:2 (0.5) to 1:1.7 (0.6).[1][2] This is in contrast to oral micronized estradiol, which has an estrone to estradiol ratio of about 5:1 (an 8- to 10-fold difference in ratio relative to oral estradiol decanoate in oil).[4] The normal ratio of estrone to estradiol in women is about 1:2 (0.5) in premenopausal women and about 2:1 in postmenopausal women.[4] As such, oral estradiol decanoate in oil may provide a more physiological and favorable profile of estrone and estradiol levels than oral micronized estradiol.[1][2]
The improved estrone to estradiol ratio of oral estradiol decanoate in oil is likely related to absorption via the intestinal lymphatic system, which allows for bypassing of first-pass metabolism in the liver.[5] This is dependent on the fatty acid decanoate ester of estradiol decanoate, and in accordance, oral estradiol decanoate not dissolved in oil has less or absent effects in rodents.[5] Absorption of oral estradiol decanoate in oil via the lymphatic system is analogous to the case of oral testosterone undecanoate in oil.[6]
See also
References
- ↑ 1.0 1.1 1.2 1.3 "Effects of orally administered oestradiol decanoate on plasma oestradiol, oestrone and gonadotrophin levels, vaginal cytology, cervical mucus and endometrium in ovariectomized women". Clin. Endocrinol. (Oxf) 7 (1): 73–7. July 1977. doi:10.1111/j.1365-2265.1977.tb02941.x. PMID 880735.
- ↑ 2.0 2.1 2.2 2.3 "Effects of estradiol decanoate in ovariectomized women". J. Endocrinol. Invest. 1 (2): 101–6. 1978. doi:10.1007/BF03350355. PMID 755846.
- ↑ Ranjit Roy Chaudhury (1 January 1981). Pharmacology of Estrogens. Elsevier Science & Technology Books. p. 36. ISBN 978-0-08-026869-9. https://books.google.com/books?id=ZIQTAQAAMAAJ.
- ↑ 4.0 4.1 "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 (Suppl 1): 3–63. 2005. doi:10.1080/13697130500148875. PMID 16112947. http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf.
- ↑ 5.0 5.1 "Oestrogenic activity of oestradiol-decanoate after oral administration to rodents". Acta Endocrinol. 85 (2): 422–8. June 1977. doi:10.1530/acta.0.0850422. PMID 577331.
- ↑ Alexandre Hohl (30 March 2017). Testosterone: From Basic to Clinical Aspects. Springer. pp. 207–. ISBN 978-3-319-46086-4. https://books.google.com/books?id=Et6TDgAAQBAJ&pg=PA207.
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