Estradiol anthranilate

Estradiol anthranilate
Clinical data
Other names	Estradiol 3-anthranilate
Routes of; administration	By mouth[1][2]
Drug class	Estrogen; 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-aminobenzoate;
CAS Number	111111-97-8;
PubChem CID	183167;
ChemSpider	159275;
Chemical and physical data
Formula	C25H29NO3
Molar mass	391.511 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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]

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.
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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[pmid3244608-1] 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.

[LokindLorenzen1991-2] 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.

[OettelSchillinger2012-3] 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.

[StellaBorchardt2007-4] 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.CS1 maint: multiple names: authors list (link)

[HansenMørk1992-5] 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.

Estradiol anthranilate

See also

References