Dual effects of macrolide antibiotics on rat liver cytochrome P-450. Induction and formation of metabolite-complexes: a structure-activity relationship

Biochem Pharmacol. 1983 Aug 1;32(15):2309-18. doi: 10.1016/0006-2952(83)90178-8.

Abstract

Previous studies have shown that the macrolide antibiotics, troleandomycin and erythromycin, are able to induce their own transformation into a metabolite forming an inactivated complex with rat liver cytochrome P-450. This paper reports the results of a study on the effects of several macrolide antibiotics including oleandomycin, erythromycin derivatives, josamycin, methymycin, tylosin, spiramycin and rifampicin, as well as antibiotics of other series, such as tetracycline and lincomycin, on rat liver cytochromes P-450 in vivo and in vitro. Only the antibiotics containing the desosamine and mycaminose amino sugars were able to give the dual effects already found with troleandomycin: induction of cytochrome p-450 and formation of an inhibitory cytochrome P-450--iron--nitrosoalkane metabolite complex in vivo or in vitro. From these studies, it appears that two structural factors are important for a macrolide antibiotic to lead to such effects: the presence of a non-hindered readily accessible N-dimethylamino group and the hydrophobic character of the molecule. These data are discussed in relation to the adverse effects observed during drug associations involving some of these macrolide antibiotics.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / pharmacology*
  • Cytochrome P-450 Enzyme System / metabolism*
  • Erythromycin / pharmacology
  • Liver / drug effects
  • Liver / enzymology*
  • Male
  • Phenobarbital / pharmacology
  • Rats
  • Rats, Inbred Strains
  • Structure-Activity Relationship
  • Troleandomycin / pharmacology

Substances

  • Anti-Bacterial Agents
  • Erythromycin
  • Cytochrome P-450 Enzyme System
  • Troleandomycin
  • Phenobarbital