Estradiol anthranilate
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]
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| Other names | Estradiol 3-anthranilate |
| Routes of administration | By mouth[1][2] |
| Drug class | Estrogen; Estrogen ester |
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| Formula | C25H29NO3 |
| Molar mass | 391.511 g·mol−1 |
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References
- 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.
- 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.
- 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.
- 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.CS1 maint: multiple names: authors list (link)
- 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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