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]

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 Y
PubChem CID	183167
ChemSpider	159275
UNII	O6PNX53TGK
CompTox Dashboard (EPA)	DTXSID70912000
Chemical and physical data
Formula	C25H29NO3
Molar mass	391.511 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

See also

• List of estrogen esters § Estradiol esters