| Identification | Back Directory | [Name]
4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY STANDARD', 97 | [CAS]
14206-58-7 | [Synonyms]
Oxytetracycline IMpurity A
[4R-(4α,4aβ,5β,5aβ,6α,12aβ]-
4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY ST
4-Epioxytetracycline,97%,'can be used as secondary standard'
4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY STANDARD', 97
4-Epioxytetracycline, 'can be used as secondary standard', 97% | [EINECS(EC#)]
204-888-2 | [Molecular Formula]
C22H24N2O9 | [MDL Number]
MFCD00062825 | [MOL File]
14206-58-7.mol | [Molecular Weight]
460.434 |
| Chemical Properties | Back Directory | [Appearance]
greenish-beige to brownish powder | [Melting point ]
168°C | [Boiling point ]
839.6±65.0 °C(Predicted) | [density ]
1.71±0.1 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under Inert Atmosphere | [solubility ]
DMSO: slightly soluble; Methanol: slightly, heated | [form ]
Powder | [pka]
4.50±1.00(Predicted) | [color ]
Greenish-beige to brownish | [Stability:]
Hygroscopic, Light Sensitive, Unstable in Solution | [EPA Substance Registry System]
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4R,4aR,5S,5aR,6S,12aS)- (14206-58-7) |
| Hazard Information | Back Directory | [Chemical Properties]
greenish-beige to brownish powder | [Uses]
A metabolite of Oxytetracycline | [Uses]
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. | [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. | [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. |
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