Estradiol acetylsalicylate

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.^{[1][2][3][4][5]} In dogs, the oral bioavailability of estradiol acetylsalicylate was found to be 17-fold higher than that of unmodified estradiol.^[1][4] 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.^[2][4][6]

Estradiol acetylsalicylate

Clinical data
Other names	Estradiol 3-acetylsalicylate; Acetylsalicylate estradiol
Routes of administration	By mouth
Drug class	Estrogen; Estrogen ester
Identifiers
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
CAS Number	111111-98-9 Y
PubChem CID	183168
ChemSpider	159276
UNII	J9B90ASJ1Y
CompTox Dashboard (EPA)	DTXSID30912001
Chemical and physical data
Formula	C27H30O5
Molar mass	434.532 g·mol−1
3D model (JSmol)	Interactive image
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
InChI InChI=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 Key:KNJUTXJFANOVGR-HXVSAZQXSA-N

See also

• List of estrogen esters § Estradiol esters