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Estradiol diacetate
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{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-3-acetyloxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-17-yl] acetate | image = estradiol diacetate.svg | width = <!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = [[Estrogen (medication)|Estrogen]]; [[Estrogen ester]] <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 3434-88-6 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 66431 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 59804 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = X43EU3CQ8P | KEGG = | ChEBI = | ChEMBL = 3138724 | synonyms = EDA; Estradiol 3,17β-diacetate; NSC-106559 <!--Chemical data--> | C=22 | H=28 | O=4 | SMILES = CC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)OC(=O)C)C | StdInChI_Ref = | StdInChI = 1S/C22H28O4/c1-13(23)25-16-5-7-17-15(12-16)4-6-19-18(17)10-11-22(3)20(19)8-9-21(22)26-14(2)24/h5,7,12,18-21H,4,6,8-11H2,1-3H3/t18-,19-,20+,21+,22+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = VQHQLBARMFAKSV-AANPDWTMSA-N }} '''Estradiol diacetate''' ('''EDA'''), or '''estradiol 3,17β-diacetate''', is an [[estrogen (medication)|estrogen]] and an [[estrogen ester]]—specifically, the C3 and C17β [[acetate|diacetate]] [[ester]] of [[estradiol (medication)|estradiol]]—which was never marketed.<ref name="pmid13531579">{{cite journal | vauthors = Junkmann K, Witzel H | title = Chemie und Pharmakologie von Steroidhormon-Estern | trans-title = Chemistry and pharmacology of steroid hormone esters | language = de | journal = Z Vitam Horm Fermentforsch | volume = 9 | issue = 1–2 | pages = 97–143 contd | date = 1957 | pmid = 13531579 }}</ref><ref name="pmid6705734">{{cite journal | vauthors = Janocko L, Larner JM, Hochberg RB | title = The interaction of C-17 esters of estradiol with the estrogen receptor | journal = Endocrinology | volume = 114 | issue = 4 | pages = 1180–6 | date = April 1984 | pmid = 6705734 | doi = 10.1210/endo-114-4-1180 }}</ref><ref name="pmid21038436">{{cite journal | vauthors = Mu Y, Peng S, Zhang A, Wang L | title = Role of pocket flexibility in the modulation of estrogen receptor alpha by key residue arginine 394 | journal = Environ. Toxicol. Chem. | volume = 30 | issue = 2 | pages = 330–6 | date = February 2011 | pmid = 21038436 | doi = 10.1002/etc.389 | bibcode = 2011EnvTC..30..330M | s2cid = 22116062 }}</ref><ref name="Derz1976">{{cite book | editor = Friedrich W. Derz | date = 1976 | title = ChemPRODUCTindex, Volumes 1-2 | publisher = De Gruyter | pages = 881– | isbn = 978-3-11-002141-7 | oclc = 2619908 | url = https://books.google.com/books?id=KaAgAAAAMAAJ&pg=PA881}}</ref> It is related to the [[estradiol ester|estradiol monoester]]s [[estradiol acetate]] (estradiol 3-acetate; Femtrace) and [[estradiol 17β-acetate]].<ref name="pmid13531579" /><ref name="Derz1976" /> {{Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors}} ==See also== * [[List of estrogen esters#Estradiol esters|List of estrogen esters § Estradiol esters]] ==References== {{Reflist}} {{Estradiol}} {{Estrogen receptor modulators}} [[Category:Abandoned drugs]] [[Category:Acetate esters]] [[Category:Estradiol esters]] [[Category:Secondary alcohols]] [[Category:Synthetic estrogens]] {{Steroid-stub}} {{Genito-urinary-drug-stub}}
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