| Identification | Back Directory | [Name]
ALPHA-APO-OXYTETRACYCLINE | [CAS]
18751-99-0 | [Synonyms]
β-Apo-oxytetracycline
b-Apo-oxytetracycline
BETA-APO-OXYTETRACYCLINE
ALPHA-APO-OXYTETRACYCLINE
Apooxytetracycline, beta-
beta-Apo-oxytetracycline, 'can be used as secondary standard' | [Molecular Formula]
C22H22N2O8 | [MDL Number]
MFCD00062827 | [MOL File]
18751-99-0.mol | [Molecular Weight]
442.42 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow-brown to brown powder | [Uses]
Oxytetracycline metabolite (absolute stereochemistry unknown) | [Uses]
β-Apooxytetracycline is a degradation product of oxytetracycline formed under acidic conditions. After initial dehydration to anhydrooxytetracycline, it undergoes an internal cyclisation of the C5-OH to the C12 ketone. The resulting cleavage of the C12-C12a bond generates two isomers, α- and β-apooxytetracycline. β-Apooxytetracycline is an important standard for monitoring oxytetracycline stability. | [Uses]
β-Apooxytetracycline is a degradation product of oxytetracycline formed under acidic conditions. An initial dehydration to anhydrooxytetracycline then undergoes an internal cyclisation of the C5-OH to the C12 ketone. The resulting cleavage of the C12-C12a bond generates two isomers, α- and β-apooxytetracycline. β-apooxytetracycline is an important standard for monitoring oxytetracycline stability. | [Description]
β-Apooxytetracycline is a potential impurity found in commercial preparations of oxytetracycline. β-Apooxytetracycline is a degradation product formed from oxytetracycline via acid hydrolysis. It has a relative potency of 0.1 compared with oxytetracycline for inhibiting the growth of aerobic sludge bacteria, an MIC50 value of 32 mg/L for tetracycline-sensitive strains of Pseudomonas, and MIC50 values of greater than 32 mg/L for tetracycline-sensitive strains of Agrobacterium, Moraxella, and Bacillus, as well as tetracycline-resistant strains of E. coli. β-Apooxytetracycline (10 mg/kg) is toxic to rats, decreasing body weight, disrupting blood cell counts, and inducing hepatocyte necrosis. | [References]
[1] 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
[2] B. 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 3: 263-271. DOI: 10.1007/s00244-001-0017-2
[3] N. HUE. PRELIMINARY STUDIES ON THE TOXIC EFFECTS OF DEGRADATION PRODUCTS OF OXYTETRACYCLINE AND CHLORTETRACYCLINE ON RATS[J]. Hue University Journal of Science: Natural Science, 2015, 438 1: 467-475. DOI: 10.17265/2161-6256/2015.12.004 |
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