4-Epioxytetracycline

Description

Epioxytetracycline is a degradation product of the antibiotic oxytetracycline . It has been found in swine manure compost and wastewater and is considered a pollutant.

Chemical properties

greenish-beige to brownish powder

The Uses of 4-Epioxytetracycline

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.

The Uses of 4-Epioxytetracycline

A metabolite of Oxytetracycline

What are the applications of Application

4-Epioxytetracycline is a metabolite of Oxytetracycline (OTC)

Mode of action

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.

References

1] I V BELIAVSKAIA. [Study of the mechanism of action of minocycline and of certain other tetracycline group compounds].[J]. Antibiotiki, 1976, 21 3: 242-245.
[2] BENT HALLING-S?RENSEN J. T G Sengel?v. Toxicity of Tetracyclines and Tetracycline Degradation Products to Environmentally Relevant Bacteria, Including Selected Tetracycline-Resistant Bacteria[J]. Archives of Environmental Contamination and Toxicology, 2002, 42 1: 263-271. DOI:10.1007/s00244-001-0017-2.
[3] ANNE KRUSE LYKKEBERG . Quantitative analysis of oxytetracycline and its impurities by LC-MS-MS[J]. Journal of pharmaceutical and biomedical analysis, 2004, 34 2: Pages 325-332. DOI:10.1016/S0731-7085(03)00500-4.
[4] RICHENG XUAN. Hydrolysis and photolysis of oxytetracycline in aqueous solution.[J]. Journal of Environmental Science and Health Part B-pesticides Food Contaminants and Agricultural Wastes, 2010, 45 1: 73-81. DOI:10.1080/03601230903404556.
[5] HONGXING HAN. Impact of 4-epi-oxytetracycline on the gut microbiota and blood metabolomics of Wistar rats[J]. Scientific Reports, 2016, 6 1. DOI:10.1038/srep23141.