Chemistry:17β-Aminoestrogen

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Short description: Class of chemical compounds
Prolame, a 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]

References

  1. ↑ 1.0 1.1 1.2 "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. 1993. doi:10.1016/0039-128x(93)90002-5. PMID 8256254. 
  2. ↑ 2.0 2.1 2.2 2.3 "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. 2010. doi:10.1016/j.atherosclerosis.2009.06.017. PMID 19615684. 
  3. ↑ "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. 2013. doi:10.1016/j.ejphar.2012.12.030. PMID 23305838. 
  4. ↑ "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. 1993. PMID 8378368. 




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