17β-Aminoestrogen

17β-Aminoestrogens are a group of synthetic, steroidal estrogens derived from estradiol which have an amine substitution in place of the hydroxyl group at the C17β position.[1][2] They are estrogenic similarly,[1] but, unlike estradiol, show sustained anticoagulant activity that appears to be mediated by non-genomic mechanisms.[2] As such, it is thought that they may have a reduced risk of venous thromboembolism.[2] The 17β-aminoestrogens include the base or parent estrogen aminoestradiol (AE2)[3] and the extended-chain derivatives butolame, hexolame, pentolame, prodiame, and prolame.[1][2] They are a homologous series of steroids.[4]

Prolame, a 17β-aminoestrogen.

References
  1. Lemini C, Rubio-Póo C, Silva G, García-Mondragón J, Zavala E, Mendoza-Patiño N, Castro D, Cruz-Almanza R, Mandoki JJ (1993). "Anticoagulant and estrogenic effects of two new 17 beta-aminoestrogens, butolame [17 beta-(4-hydroxy-1-butylamino)-1,3,5(10)-estratrien-3-ol] and pentolame [17 beta-(5-hydroxy-1-pentylamino)-1,3,5(10)-estratrien-3-ol]". Steroids. 58 (10): 457–61. doi:10.1016/0039-128x(93)90002-5. PMID 8256254. S2CID 54381037.
  2. González G, Alvarado-Vasquez N, Fernández-G JM, Cruz-Robles D, Del Valle L, Pinzón E, Torres I, Rodriguez E, Zapata E, Gómez-Vidales V, Montaño LF, de la Peña A (2010). "The antithrombotic effect of the aminoestrogen prolame (N-(3-hydroxy-1,3,5(10)-estratrien-17B-YL)-3-hydroxypropylamine) is linked to an increase in nitric oxide production by platelets and endothelial cells". Atherosclerosis. 208 (1): 62–8. doi:10.1016/j.atherosclerosis.2009.06.017. PMID 19615684.
  3. 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.
  4. Rubio-Póo C, Lemini C, Silva G, García-Mondragón J, Zavala E, Castro D, Mendoza-Patiño N, Mandoki JJ (1993). "Comparison of the time course of anticoagulant and estrogenic effects of prolame, butolame, pentolame and hexolame, a homologous series of 17 beta-amino estrogens". Proc. West. Pharmacol. Soc. 36: 143–7. PMID 8378368.


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