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Estradiol decanoate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
  • [(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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC28H42O3
Molar mass426.641 g·mol−1
3D model (JSmol)
  • CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
  • 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

Estradiol decanoate (E2D), orestradiol decylate, also known asestradiol 17β-decanoate, is asyntheticsteroidalestrogen and anestrogen ester – specifically, the 17β-decanoate (decylate)ester ofestradiol – which was studied for use inhormone replacement therapy forovariectomized women in the late 1970s but was never marketed.[1][2][3]

Oral estradiol decanoate inoil at a dosage of 0.25 to 0.5 mg/day for 14 days has been studied inovariectomized women and found to produce levels ofestrone 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 toabsorption via theintestinallymphatic system, which allows for bypassing offirst-pass metabolism in theliver.[5] This is dependent on thefatty 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 oraltestosterone undecanoate in oil.[6]

See also

[edit]

References

[edit]
  1. ^abcdKicovic 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. ^abcdLuisi 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. ^abKuhl 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. ^abde 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.
Topics
Esters
Related
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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