Estradiol decanoate

{{Short description|Chemical compound}}

{{Drugbox

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| 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

| image = Estradiol decanoate.svg

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| routes_of_administration = By mouth

| class = Estrogen; Estrogen ester

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 61748-93-4

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| PubChem = 66409

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| ChemSpiderID = 59783

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S4J8Z2L5LZ

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| synonyms = E2D; Estradiol decylate; Estradiol 17β-decanoate; Estra-1,3,5(10)-triene-3,17β-diol 17β-decanoate

| C=28 | H=42 | O=3

| SMILES = CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = YYFQNZXJGOTFRX-VMBLQBCYSA-N

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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.{{cite journal | vauthors = Kicovic PM, Luisi M, Franchi F, Alicicco E | title = Effects of orally administered oestradiol decanoate on plasma oestradiol, oestrone and gonadotrophin levels, vaginal cytology, cervical mucus and endometrium in ovariectomized women | journal = Clin. Endocrinol. (Oxf) | volume = 7 | issue = 1 | pages = 73–7 | date = July 1977 | pmid = 880735 | doi = 10.1111/j.1365-2265.1977.tb02941.x | s2cid = 13639429 }}{{cite journal | vauthors = Luisi M, Kicovic PM, Alicicco E, Franchi F | title = Effects of estradiol decanoate in ovariectomized women | journal = J. Endocrinol. Invest. | volume = 1 | issue = 2 | pages = 101–6 | year = 1978 | pmid = 755846 | doi = 10.1007/BF03350355 | s2cid = 38187367 }}{{cite book|author=Ranjit Roy Chaudhury|title=Pharmacology of Estrogens|url=https://books.google.com/books?id=ZIQTAQAAMAAJ|date=1 January 1981|publisher=Elsevier Science & Technology Books|isbn=978-0-08-026869-9|page=36}}

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). 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).{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | pages = 3–63 | year = 2005 | issue = Suppl 1 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}} 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. As such, oral estradiol decanoate in oil may provide a more physiological and favorable profile of estrone and estradiol levels than oral micronized estradiol.

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.{{cite journal | vauthors = de Visser J, van der Vies J | title = Oestrogenic activity of oestradiol-decanoate after oral administration to rodents | journal = Acta Endocrinol. | volume = 85 | issue = 2 | pages = 422–8 | date = June 1977 | pmid = 577331 | doi = 10.1530/acta.0.0850422}} 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. Absorption of oral estradiol decanoate in oil via the lymphatic system is analogous to the case of oral testosterone undecanoate in oil.{{cite book|author=Alexandre Hohl|title=Testosterone: From Basic to Clinical Aspects|url=https://books.google.com/books?id=Et6TDgAAQBAJ&pg=PA207|date=30 March 2017|publisher=Springer|isbn=978-3-319-46086-4|pages=207–}}