| 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. |
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