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Chemical compound
Pharmaceutical compound
Estradiol cyclooctyl acetate Other names E2 COA; Estradiol cyclooctylacetate; Estradiol 17β-cyclooctylacetate; Estra-1,3,5(10)-triene-3,17β-diol 17β-cyclooctylacetate Routes of By mouth Drug class Estrogen ; Estrogen ester
[(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 ) Formula C 28 H 40 O 3 Molar mass −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 (E2 COA ), 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-cyclooctyl acetate 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] oral bioavailability than does micronized estradiol due to absorption via the lymphatic system and hence partial bypassing of first-pass metabolism .[ 4] [ 1] liver parameters such as changes in sex hormone-binding globulin production.[ 4] desogestrel as a birth control pill , but resulted in unacceptable menstrual bleeding patterns and was not further developed.[ 1]
^ a b c Bastianelli 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 . ^ 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 . ^ 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 . ^ a b c Schubert 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 .
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol
Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol
Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
Estrofurate Estrogenic substances Estromustine Estrone
Etamestrol (eptamestrol) Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )Coumestans (e.g., coumestrol , psoralidin )Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )Lavender oil Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )Metalloestrogens (e.g., cadmium )Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )Steroid -like (e.g., deoxymiroestrol , miroestrol )Stilbenoids (e.g., resveratrol , rhaponticin )Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )Others (e.g., agnuside , rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
