A new structural alert for benzimidazoles: 2,6-dimethylphenyl substituents increase mutagenic potential and time-dependent CYP3A4 inhibition risk

Bioorg Med Chem Lett. 2011 Mar 1;21(5):1422-4. doi: 10.1016/j.bmcl.2011.01.023. Epub 2011 Jan 11.

Abstract

A series of 2-[(2,6)-dimethylphenyl]benzimidazole analogs displayed strong potential for mutagenicity following metabolic activation in either TA98 or TA100 Salmonella typhimurium strains. The number of revertants was significantly reduced by replacing the 2,6-dimethylphenyl group with a 2,6-dichlorophenyl moiety. Time-dependent CYP3A4 inhibition was also observed with a compound containing a 2-[(2,6)-dimethylphenyl] benzimidazole ring, implying risk for this scaffold to generate reactive metabolites.

MeSH terms

  • Albendazole / pharmacology
  • Anthelmintics / pharmacology*
  • Benzimidazoles / pharmacology*
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 CYP3A Inhibitors*
  • Mutagenicity Tests
  • Mutagens / pharmacology*
  • Salmonella typhimurium / drug effects*
  • Salmonella typhimurium / genetics
  • Time Factors

Substances

  • Anthelmintics
  • Benzimidazoles
  • Cytochrome P-450 CYP3A Inhibitors
  • Mutagens
  • benzimidazole
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Albendazole