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 namesAE2; 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
ChemSpider
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
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

References
  1. Lemini C, Rubio-Póo C, Franco Y, Jaimez R, Avila ME, Medina M, Lemus AE (2013). "In vivo profile of the anticoagulant effect of 17ß-amino-1,3,5(10)estratrien-3-ol". Eur. J. Pharmacol. 700 (1–3): 210–6. doi:10.1016/j.ejphar.2012.12.030. PMID 23305838.
  2. Lemini C, Jaimez R, Pozas R, Franco Y, Avila ME, Figueroa A, Medina M, Lemus AE, García-Becerra R, Ordaz-Rosado D, Larrea F (2015). "In vivo and in vitro estrogenic profile of 17β-amino-1,3,5(10)estratrien-3-ol". J. Steroid Biochem. Mol. Biol. 147: 40–7. doi:10.1016/j.jsbmb.2014.11.019. PMID 25448750. S2CID 195676484.
  3. Ye YH, Huang YS, Wang ZQ, Chen SM, Tian Y (1993). "Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor". Steroids. 58 (1): 35–9. doi:10.1016/0039-128x(93)90015-f. PMID 8430443. S2CID 54308145.
  4. Li Z, Yan M, Li Z, Vuki M, Wu D, Liu F, Zhong W, Zhang L, Xu D (2012). "A multiplexed screening method for agonists and antagonists of the estrogen receptor protein". Anal Bioanal Chem. 403 (5): 1373–84. doi:10.1007/s00216-012-5933-7. PMID 22453607. S2CID 22670785.
  5. Lemini C, Cruz-Ramos E, Toscano RA, Cruz-Almanza R (1998). "A comparative structural study of the steroid epimers: 17 beta-amino-1,3,5(10)-estratrien-3-ol, 17 alpha-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis". Steroids. 63 (11): 556–64. doi:10.1016/s0039-128x(98)00063-4. PMID 9830681. S2CID 40400348.


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