Aminoestradiol

Aminoestradiol (AE₂), also known as 17β-aminoestradiol (17βAE₂) or as 17β-aminoestra-1,3,5(10)-trien-3-ol, is a synthetic, steroidal estrogen and a 17β-aminoestrogen with anticoagulant effects that was never marketed.^{[1][2][3][4][5]} It is an analogue of estradiol in which the C17β hydroxyl group has been replaced with an amine group.^[1][2] AE₂ has profoundly reduced estrogenic potency compared to estradiol; its EC₅₀ for activation of the ERα was found to be 1.82 μM, whereas that of estradiol was 2.14 nM (relative potency 0.12 for AE₂ versus 100 for estradiol, or roughly a 1,000-fold difference).^[2] It binds with low relative affinity to both the ERα and ERβ and has estrogenic activity that is greatly mediated through the ERβ and to a lesser extent through the ERα.^[2]

Aminoestradiol

Clinical data
Other names	AE2; 17βAE2; 17β-Aminoestra-1,3,5(10)-trien-3-ol; 3-Hydroxy-17β-aminoestra-1,3,5(10)-triene
Identifiers
IUPAC name (8R,9S,13S,14S,17S)-17-Amino-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
PubChem CID	11231075
ChemSpider	9406123
CompTox Dashboard (EPA)	DTXSID401337012
Chemical and physical data
Formula	C18H25NO
Molar mass	271.404 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2N)CCC4=C3C=CC(=C4)O
InChI InChI=1S/C18H25NO/c1-18-9-8-14-13-5-3-12(20)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-17,20H,2,4,6-9,19H2,1H3/t14-,15-,16+,17+,18+/m1/s1 Key:VPONVJPFULJPAN-ZBRFXRBCSA-N