Estradiol cyclooctyl acetate

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Estradiol cyclooctyl acetate
Estradiol cyclooctyl acetate.svg
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
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC28H40O3
Molar mass424.625 g·mol−1
3D model (JSmol)

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]

See also[edit]

References[edit]

  1. ^ a b c 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.
  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.
  4. ^ a b c 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.