Aminoestradiol

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;
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;

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]

References

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.
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.
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. PMID 8430443.
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.
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.

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[pmid23305838-1] 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.

[pmid25448750-2] 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.

[pmid8430443-3] 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. PMID 8430443.

[pmid22453607-4] 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.

[pmid9830681-5] 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.