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][3] 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 namesEstradiol 3-acetylsalicylate; Acetylsalicylate estradiol
Routes of
administration		By mouth
Drug classEstrogen; 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
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H30O5
Molar mass434.532 g·mol−1
3D model (JSmol)
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

References
  1. 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. S2CID 7308414.
  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. 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. 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.{{cite book}}: CS1 maint: multiple names: authors list (link)
  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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