Estradiol acetylsalicylate explained

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. 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.^[6]

See also

• List of estrogen esters § Estradiol esters

Notes and References

1. Hussain MA, Aungst BJ, Shefter E . Prodrugs for improved oral beta-estradiol bioavailability . Pharmaceutical Research . 5 . 1 . 44–47 . January 1988 . 3244608 . 10.1023/A:1015863412137 . 7308414 .
2. Lokind KB, Lorenzen FH, Bundgaard H . Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat. International Journal of Pharmaceutics. 76. 1–2. 1991. 177–182. 0378-5173. 10.1016/0378-5173(91)90356-S.
3. Book: Kuhnz W, Blode, Zimmerman H . Handbook of Experimental Pharmacology . Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens . Oettel M, Schillinger E . Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA263. 6 December 2012. 135 / 2 . Springer Science & Business Media. 978-3-642-60107-1. 263– . 10.1007/978-3-642-60107-1_15 .
4. Book: Aungst BJ, Matz N . Biotechnology: Pharmaceutical Aspects . Prodrugs to Reduce Presystemic Metabolism . Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J . Prodrugs: Challenges and Rewards. https://books.google.com/books?id=Ld4scqFQmgYC&pg=PA347. 26 August 2007. Springer Science & Business Media. 978-0-387-49785-3. 347– . 10.1007/978-0-387-49785-3_8 .
5. Book: Moridani MY . Reducing Presystemic Drug Metabolism . Rautio J . Prodrugs and Targeted Delivery: Towards Better ADME Properties . https://books.google.com/books?id=jYI5jtMA2qgC&pg=PA218. 11 January 2011. John Wiley & Sons. 978-3-527-63318-0. 218–.
6. Hansen J, Mørk N, Bundgaard H . Phenyl carbamates of amino acids as prodrug forms for protecting phenols against first-pass metabolism. International Journal of Pharmaceutics. 81. 2–3. 1992. 253–261. 0378-5173. 10.1016/0378-5173(92)90017-V.