4-Epioxytetracycline

Epioxytetracycline is a metabolite of Oxytetracycline. It has been found in swine manure compost and wastewater and is considered a pollutant. This highly pure metabolite can be used as a secondary reference standard during stability studies of oxytetracycline. It can also be used to study the degradation pathway and products of tetracyclines.

greenish-beige to brownish powder

Epioxytetracycline is a degradation product of oxytetracycline formed by the epimerisation of the dimethylamino group at C4 in solution at neutral to acidic pH. The epimerisation is associated with a loss of antibiotic activity. Epioxytetracycline is an important standard for monitoring oxytetracycline stability.

Oxytetracycline causes inhibition of protein synthesis. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome.
In an acellular model system of protein synthesis using ribosomes from tetracycline-sensitive and resistant strains of E. coli in the synthesis of polyphenylalanine, Oxytetracycline showed inhibitory activity along with minocycline. 4-Epioxytetracycline and beta-apo-oxytetracycline had competing properties with respect to oxytetracycline at the stage of penetration through the cell membrane but did not, however, suppress the synthesis of polyphenylalanine.

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