Estradiol acetylsalicylate

Chemical compound
Estradiol acetylsalicylate
Clinical data
Other namesEstradiol 3-acetylsalicylate; Acetylsalicylate estradiol
Routes of
administration		By mouth
Drug classEstrogen; Estrogen ester
Identifiers
  • [(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 checkY
PubChem CID
  • 183168
ChemSpider
  • 159276
UNII
  • J9B90ASJ1Y
Chemical and physical data
FormulaC27H30O5
Molar mass434.532 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

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]

See also

References

  1. ^ a b Hussain MA, Aungst BJ, Shefter E (January 1988). "Prodrugs for improved oral beta-estradiol bioavailability". Pharmaceutical Research. 5 (1): 44–47. doi:10.1023/A:1015863412137. PMID 3244608. S2CID 7308414.
  2. ^ a b Lokind KB, Lorenzen FH, Bundgaard H (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. ^ Kuhnz W, Blode, Zimmerman H (6 December 2012). "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. pp. 263–. doi:10.1007/978-3-642-60107-1_15. ISBN 978-3-642-60107-1.
  4. ^ a b c Aungst BJ, Matz N (26 August 2007). "Prodrugs to Reduce Presystemic Metabolism". In Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J (eds.). Prodrugs: Challenges and Rewards. Biotechnology: Pharmaceutical Aspects. Springer Science & Business Media. pp. 347–. doi:10.1007/978-0-387-49785-3_8. ISBN 978-0-387-49785-3.
  5. ^ Moridani MY (11 January 2011). "Reducing Presystemic Drug Metabolism". In Rautio J (ed.). Prodrugs and Targeted Delivery: Towards Better ADME Properties. John Wiley & Sons. pp. 218–. ISBN 978-3-527-63318-0.
  6. ^ Hansen J, Mørk N, Bundgaard H (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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TopicsEsters
Related
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ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
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