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Estradiol cyclooctyl acetate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Estradiol cyclooctyl acetate
Clinical data
Other namesE2COA; Estradiol cyclooctylacetate; Estradiol 17β-cyclooctylacetate; Estra-1,3,5(10)-triene-3,17β-diol 17β-cyclooctylacetate
Routes of
administration
By mouth
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] 2-cyclooctylacetate
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC28H40O3
Molar mass424.625 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CC4CCCCCCC4)CCC5=C3C=CC(=C5)O
  • InChI=1S/C28H40O3/c1-28-16-15-23-22-12-10-21(29)18-20(22)9-11-24(23)25(28)13-14-26(28)31-27(30)17-19-7-5-3-2-4-6-8-19/h10,12,18-19,23-26,29H,2-9,11,13-17H2,1H3/t23-,24-,25+,26+,28+/m1/s1
  • Key:CZCGBAHDFURTGU-VMBLQBCYSA-N

Estradiol cyclooctyl acetate (E2COA), orestradiol 17β-cyclooctylacetate, also known asestra-1,3,5(10)-triene-3,17β-diol 17β-cyclooctylacetate, is anestrogenmedication and anestrogen ester – specifically, the 17β-cyclooctylacetateester ofestradiol – which has been studied for use inhormone replacement therapy forovariectomized women and as ahormonal contraceptive in combination with aprogestin but was never marketed.[1][2][3][4] It has greateroralbioavailability than doesmicronized estradiol due toabsorption via thelymphatic system and hence partial bypassing offirst-pass metabolism.[4][1] It is approximately twice as potent as micronized estradiol orally and has a comparatively reduced impact onliver parameters such as changes insex hormone-binding globulin production.[4] It was investigated in combination withdesogestrel as abirth control pill, but resulted in unacceptablemenstrual bleeding patterns and was not further developed.[1]

See also

[edit]

References

[edit]
  1. ^abcBastianelli C, Farris M, Rosato E, Brosens I, Benagiano G (November 2018). "Pharmacodynamics of combined estrogen-progestin oral contraceptives 3. Inhibition of ovulation".Expert Review of Clinical Pharmacology.11 (11):1085–1098.doi:10.1080/17512433.2018.1536544.PMID 30325245.S2CID 53246678.
  2. ^Dahlgren E, Crona N, Janson PO, Samsioe G (1985). "Oral replacement with estradiol-cyclooctyl acetate: a new estradiol analogue. Effects on serum lipids, proteins, gonadotrophins, estrogens and uterine endometrial morphology".Gynecologic and Obstetric Investigation.20 (2):84–90.doi:10.1159/000298978.PMID 3932144.
  3. ^Schubert W, Cullberg G (1987). "Ovulation inhibition with 17 beta-estradiol cyclo-octyl acetate and desogestrel".Acta Obstetricia et Gynecologica Scandinavica.66 (6):543–547.doi:10.3109/00016348709015732.PMID 2962418.S2CID 73200770.
  4. ^abcSchubert W, Cullberg G (1988). "Fat-soluble 17 beta-estradiol: a way of reducing dosage in steroid hormonal substitution?".Acta Obstetricia et Gynecologica Scandinavica.67 (3):271–275.doi:10.3109/00016348809004218.PMID 2972162.S2CID 39664429.
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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