Estradiol acetylsalicylate

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] 2-acetyloxybenzoate

| image = Estradiol acetylsalicylate.svg

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| routes_of_administration = By mouth

| class = Estrogen; Estrogen ester

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 111111-98-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = J9B90ASJ1Y

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| PubChem = 183168

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| ChemSpiderID = 159276

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| synonyms = Estradiol 3-acetylsalicylate; Acetylsalicylate estradiol

| C=27 | H=30 | O=5

| SMILES = CC(=O)OC1=CC=CC=C1C(=O)OC2=CC3=C(C=C2)[C@H]4CC[C@]5([C@H]([C@@H]4CC3)CC[C@@H]5O)C

| StdInChI_Ref =

| StdInChI = 1S/C27H30O5/c1-16(28)31-24-6-4-3-5-22(24)26(30)32-18-8-10-19-17(15-18)7-9-21-20(19)13-14-27(2)23(21)11-12-25(27)29/h3-6,8,10,15,20-21,23,25,29H,7,9,11-14H2,1-2H3/t20-,21-,23+,25+,27+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = KNJUTXJFANOVGR-HXVSAZQXSA-N

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Estradiol acetylsalicylate, or estradiol 3-acetylsalicylate, is a synthetic estrogen and estrogen ester – specifically, the C3 acetylsalicylic acid (aspirin) ester of estradiol – which was described in the late 1980s and was never marketed.{{cite journal | vauthors = Hussain MA, Aungst BJ, Shefter E | title = Prodrugs for improved oral beta-estradiol bioavailability | journal = Pharmaceutical Research | volume = 5 | issue = 1 | pages = 44–47 | date = January 1988 | pmid = 3244608 | doi = 10.1023/A:1015863412137 | s2cid = 7308414 }}{{cite journal| vauthors = Lokind KB, Lorenzen FH, Bundgaard H |title=Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat|journal=International Journal of Pharmaceutics|volume=76|issue=1–2|year=1991|pages=177–182|issn=0378-5173|doi=10.1016/0378-5173(91)90356-S}}{{cite book| vauthors = Kuhnz W, Blode, Zimmerman H | series = Handbook of Experimental Pharmacology | chapter = Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens | veditors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen| chapter-url = https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA263|date=6 December 2012| volume = 135 / 2 |publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=263– | doi = 10.1007/978-3-642-60107-1_15 }}{{cite book| vauthors = Aungst BJ, Matz N | series = Biotechnology: Pharmaceutical Aspects | chapter = Prodrugs to Reduce Presystemic Metabolism | veditors = Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J |title=Prodrugs: Challenges and Rewards| chapter-url=https://books.google.com/books?id=Ld4scqFQmgYC&pg=PA347|date=26 August 2007|publisher=Springer Science & Business Media|isbn=978-0-387-49785-3|pages=347– | doi = 10.1007/978-0-387-49785-3_8 }}{{cite book| vauthors = Moridani MY | chapter = Reducing Presystemic Drug Metabolism | veditors = Rautio J |title=Prodrugs and Targeted Delivery: Towards Better ADME Properties | chapter-url=https://books.google.com/books?id=jYI5jtMA2qgC&pg=PA218|date=11 January 2011|publisher=John Wiley & Sons|isbn=978-3-527-63318-0|pages=218–}} In dogs, the oral bioavailability of estradiol acetylsalicylate was found to be 17-fold higher than that of unmodified estradiol. However, a subsequent study found that the oral bioavailability of estradiol and estradiol acetylsalicylate did not differ significantly in rats (4.3% and 4.2%, respectively), suggestive of a major species difference.{{cite journal| vauthors = Hansen J, Mørk N, Bundgaard H |title=Phenyl carbamates of amino acids as prodrug forms for protecting phenols against first-pass metabolism|journal=International Journal of Pharmaceutics|volume=81|issue=2–3|year=1992|pages=253–261|issn=0378-5173|doi=10.1016/0378-5173(92)90017-V}}