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Second-generation antibacterial benzimidazole ureas: discovery of a preclinical candidate with reduced metabolic liability.

Abstract：

:Compound 3 is a potent aminobenzimidazole urea with broad-spectrum Gram-positive antibacterial activity resulting from dual inhibition of bacterial gyrase (GyrB) and topoisomerase IV (ParE), and it demonstrates efficacy in rodent models of bacterial infection. Preclinical in vitro and in vivo studies showed that compound 3 covalently labels liver proteins, presumably via formation of a reactive metabolite, and hence presented a potential safety liability. The urea moiety in compound 3 was identified as being potentially responsible for reactive metabolite formation, but its replacement resulted in loss of antibacterial activity and/or oral exposure due to poor physicochemical parameters. To identify second-generation aminobenzimidazole ureas devoid of reactive metabolite formation potential, we implemented a metabolic shift strategy, which focused on shifting metabolism away from the urea moiety by introducing metabolic soft spots elsewhere in the molecule. Aminobenzimidazole urea 34, identified through this strategy, exhibits similar antibacterial activity as that of 3 and did not label liver proteins in vivo, indicating reduced/no potential for reactive metabolite formation.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Grillot AL,Le Tiran A,Shannon D,Krueger E,Liao Y,O'Dowd H,Tang Q,Ronkin S,Wang T,Waal N,Li P,Lauffer D,Sizensky E,Tanoury J,Perola E,Grossman TH,Doyle T,Hanzelka B,Jones S,Dixit V,Ewing N,Liao S,Boucher B,Ja

doi

10.1021/jm500563g

subject

Has Abstract

pub_date

2014-11-13 00:00:00

pages

8792-816

issue

21

eissn

0022-2623

issn

1520-4804

journal_volume

57

pub_type

杂志文章

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