Estradiol cyclooctyl acetate

Estradiol cyclooctyl acetate (E2COA), or estradiol 17β-cyclooctylacetate, also known as estra-1,3,5(10)-triene-3,17β-diol 17β-cyclooctylacetate, is an estrogen medication and an estrogen ester – specifically, the 17β-cyclooctylacetate ester of estradiol – which has been studied for use in hormone replacement therapy for ovariectomized women and as a hormonal contraceptive in combination with a progestin but was never marketed.[1][2][3][4] It has greater oral bioavailability than does micronized estradiol due to absorption via the lymphatic system and hence partial bypassing of first-pass metabolism.[4][1] It is approximately twice as potent as micronized estradiol orally and has a comparatively reduced impact on liver parameters such as changes in sex hormone-binding globulin production.[4] It was investigated in combination with desogestrel as a birth control pill, but resulted in unacceptable menstrual bleeding patterns and was not further developed.[1]

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
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] 2-cyclooctylacetate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H40O3
Molar mass424.625 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CC4CCCCCCC4)CCC5=C3C=CC(=C5)O
InChI
  • 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

See also

References
  1. Bastianelli, Carlo; Farris, Manuela; Rosato, Elena; Brosens, Ivo; Benagiano, Giuseppe (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. ISSN 1751-2433. 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". Gynecol. Obstet. Invest. 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 Obstet Gynecol Scand. 66 (6): 543–7. doi:10.3109/00016348709015732. PMID 2962418. S2CID 73200770.
  4. Schubert W, Cullberg G (1988). "Fat-soluble 17 beta-estradiol: a way of reducing dosage in steroid hormonal substitution?". Acta Obstet Gynecol Scand. 67 (3): 271–5. doi:10.3109/00016348809004218. PMID 2972162. S2CID 39664429.


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