Chemistry:Estradiol anthranilate

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Short description: Chemical compound
Estradiol anthranilate
Estradiol anthranilate.svg
Clinical data
Other namesEstradiol 3-anthranilate
Routes of
administration
By mouth[1][2]
Drug classEstrogen; Estrogen ester
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC25H29NO3
Molar mass391.511 g·mol−1
3D model (JSmol)

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. 1.0 1.1 1.2 "Prodrugs for improved oral beta-estradiol bioavailability". Pharmaceutical Research 5 (1): 44–47. January 1988. doi:10.1023/A:1015863412137. PMID 3244608. 
  2. 2.0 2.1 2.2 "Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat". International Journal of Pharmaceutics 76 (1–2): 177–182. 1991. doi:10.1016/0378-5173(91)90356-S. ISSN 0378-5173. 
  3. 3.0 3.1 "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. 135 / 2. Springer Science & Business Media. 6 December 2012. pp. 263–. doi:10.1007/978-3-642-60107-1_15. ISBN 978-3-642-60107-1. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA263. 
  4. 4.0 4.1 "Prodrugs to Reduce Presystemic Metabolism". Prodrugs: Challenges and Rewards. Biotechnology: Pharmaceutical Aspects. Springer Science & Business Media. 26 August 2007. pp. 347–. doi:10.1007/978-0-387-49785-3_8. ISBN 978-0-387-49785-3. https://books.google.com/books?id=Ld4scqFQmgYC&pg=PA347. 
  5. "Phenyl carbamates of amino acids as prodrug forms for protecting phenols against first-pass metabolism". International Journal of Pharmaceutics 81 (2–3): 253–261. 1992. doi:10.1016/0378-5173(92)90017-V. ISSN 0378-5173.