Estradiol anthranilate
Clinical data
Other namesEstradiol 3-anthranilate
Routes of
administration		By mouth[1][2]
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-aminobenzoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H29NO3
Molar mass391.511 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5N
  • InChI=1S/C25H29NO3/c1-25-13-12-18-17-9-7-16(29-24(28)20-4-2-3-5-22(20)26)14-15(17)6-8-19(18)21(25)10-11-23(25)27/h2-5,7,9,14,18-19,21,23,27H,6,8,10-13,26H2,1H3/t18-,19-,21+,23+,25+/m1/s1
  • Key:KZDLYRDWDPOBMR-CWWQDXLCSA-N

Estradiol anthranilate, or estradiol 3-anthranilate, is a synthetic estrogen and estrogen ester – specifically, the C3 anthranilic acid ester of estradiol – which was described in the late 1980s and was never marketed.[1][2][3][4] In dogs, the oral bioavailability of estradiol anthranilate was found to be 5-fold higher than that of unmodified estradiol.[1][3] However, a subsequent study found that the oral bioavailability of estradiol and estradiol anthranilate did not differ considerably in rats (4.3% and 3.2%, respectively), suggestive of a major species difference.[2][4][5]

See also

References

  1. ^ a b c 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 c 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. ^ a b 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 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. ^ 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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