Estradiol acetylsalicylate

Estradiol acetylsalicylate
Clinical data
Synonyms Estradiol 3-acetylsalicylate; Acetylsalicylate estradiol
Routes of
administration		 By mouth
Drug class Estrogen; Estrogen ester
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C27H30O5
Molar mass 434.532 g/mol
3D model (JSmol)

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][3] However, a subsequent study found that the oral bioavailability of estradiol and estradiol acetylsalicylate did not differ in rats (4.3% and 4.2%, respectively), suggestive of a major species difference.[2][4][6]

See also

References

  1. 1 2 Hussain MA, Aungst BJ, Shefter E (January 1988). "Prodrugs for improved oral beta-estradiol bioavailability". Pharm. Res. 5 (1): 44–7. doi:10.1023/A:1015863412137. PMID 3244608.
  2. 1 2 Lokind, Kenneth B.; Lorenzen, Finn Hjort; Bundgaard, Hans (1991). "Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat". International Journal of Pharmaceutics. 76 (1–2): 177–182. doi:10.1016/0378-5173(91)90356-S. ISSN 0378-5173.
  3. 1 2 Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 263–. ISBN 978-3-642-60107-1.
  4. 1 2 Valentino Stella; Ronald Borchardt; Michael Hageman; Reza Oliyai, Hans Maag, Jefferson Tilley (26 August 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 347–. ISBN 978-0-387-49785-3.
  5. ↑ Jarkko Rautio (11 January 2011). Prodrugs and Targeted Delivery: Towards Better ADME Properties. John Wiley & Sons. pp. 218–. ISBN 978-3-527-63318-0.
  6. ↑ Hansen, Joan; Mørk, Niels; Bundgaard, Hans (1992). "Phenyl carbamates of amino acids as prodrug forms for protecting phenols against first-pass metabolism". International Journal of Pharmaceutics. 81 (2–3): 253–261. doi:10.1016/0378-5173(92)90017-V. ISSN 0378-5173.



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