Estradiol cyclooctyl acetate

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| 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

| image = Estradiol cyclooctyl acetate.svg

| width = 250px

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = By mouth

| class = Estrogen; Estrogen ester

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 66791-46-6

| CAS_supplemental =

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem = 67083

| IUPHAR_ligand =

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID = 60433

| UNII =

| KEGG =

| ChEBI =

| ChEMBL =

| synonyms = E₂COA; Estradiol cyclooctylacetate; Estradiol 17β-cyclooctylacetate; Estra-1,3,5(10)-triene-3,17β-diol 17β-cyclooctylacetate

| C=28 | H=40 | O=3

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CC4CCCCCCC4)CCC5=C3C=CC(=C5)O

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = CZCGBAHDFURTGU-VMBLQBCYSA-N

}}

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.{{cite journal | vauthors = Bastianelli C, Farris M, Rosato E, Brosens I, Benagiano G | title = Pharmacodynamics of combined estrogen-progestin oral contraceptives 3. Inhibition of ovulation | journal = Expert Review of Clinical Pharmacology | volume = 11 | issue = 11 | pages = 1085–1098 | date = November 2018 | pmid = 30325245 | doi = 10.1080/17512433.2018.1536544 | s2cid = 53246678 }}{{cite journal | vauthors = Dahlgren E, Crona N, Janson PO, Samsioe G | title = Oral replacement with estradiol-cyclooctyl acetate: a new estradiol analogue. Effects on serum lipids, proteins, gonadotrophins, estrogens and uterine endometrial morphology | journal = Gynecologic and Obstetric Investigation | volume = 20 | issue = 2 | pages = 84–90 | year = 1985 | pmid = 3932144 | doi = 10.1159/000298978 }}{{cite journal | vauthors = Schubert W, Cullberg G | title = Ovulation inhibition with 17 beta-estradiol cyclo-octyl acetate and desogestrel | journal = Acta Obstetricia et Gynecologica Scandinavica | volume = 66 | issue = 6 | pages = 543–547 | year = 1987 | pmid = 2962418 | doi = 10.3109/00016348709015732 | s2cid = 73200770 }}{{cite journal | vauthors = Schubert W, Cullberg G | title = Fat-soluble 17 beta-estradiol: a way of reducing dosage in steroid hormonal substitution? | journal = Acta Obstetricia et Gynecologica Scandinavica | volume = 67 | issue = 3 | pages = 271–275 | year = 1988 | pmid = 2972162 | doi = 10.3109/00016348809004218 | s2cid = 39664429 }} It has greater oral bioavailability than does micronized estradiol due to absorption via the lymphatic system and hence partial bypassing of first-pass metabolism. 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. It was investigated in combination with desogestrel as a birth control pill, but resulted in unacceptable menstrual bleeding patterns and was not further developed.