Estradiol decanoate

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]

Estradiol decanoate
Clinical data
Other namesE2D; Estradiol decylate; Estradiol 17β-decanoate; Estra-1,3,5(10)-triene-3,17β-diol 17β-decanoate
Routes of
administration		By mouth[1][2]
Drug classEstrogen; Estrogen ester
Identifiers
IUPAC name
  • [(8R,9S,13S,14S,17S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] decanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H42O3
Molar mass426.641 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
InChI
  • InChI=1S/C28H42O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h12,14,19,23-26,29H,3-11,13,15-18H2,1-2H3/t23-,24-,25+,26+,28+/m1/s1
  • Key:YYFQNZXJGOTFRX-VMBLQBCYSA-N

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. Kicovic PM, Luisi M, Franchi F, Alicicco E (July 1977). "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. doi:10.1111/j.1365-2265.1977.tb02941.x. PMID 880735. S2CID 13639429.
  2. Luisi M, Kicovic PM, Alicicco E, Franchi F (1978). "Effects of estradiol decanoate in ovariectomized women". J. Endocrinol. Invest. 1 (2): 101–6. doi:10.1007/BF03350355. PMID 755846. S2CID 38187367.
  3. Ranjit Roy Chaudhury (1 January 1981). Pharmacology of Estrogens. Elsevier Science & Technology Books. p. 36. ISBN 978-0-08-026869-9.
  4. 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.
  5. de Visser J, van der Vies J (June 1977). "Oestrogenic activity of oestradiol-decanoate after oral administration to rodents". Acta Endocrinol. 85 (2): 422–8. doi:10.1530/acta.0.0850422. PMID 577331.
  6. Alexandre Hohl (30 March 2017). Testosterone: From Basic to Clinical Aspects. Springer. pp. 207–. ISBN 978-3-319-46086-4.


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