A potential impurity found in commercial preparations of oxytetracycline
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β-Apooxytetracycline

Item No. 27099

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,4S,5R)-4-[(3R)-1,3-dihydro-4,5-dihydroxy-9-methyl-3-oxonaphtho[2,3-c]furan-1-yl]-3-(dimethylamino)-2,5-dihydroxy-6-oxo-1-cyclohexene-1-carboxamide
CAS Number
18751-99-0
Synonyms
  • β-Apo-Oxytetracycline
  • β-Apoterramycin
Molecular Formula
C22H22N2O8
Formula Weight
442.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 0.2 mg/ml
λmax
215, 244, 321, 373 nm
SMILES
OC1=CC=CC2=C1C(O)=C3C([C@]([C@]4([H])[C@@H](O)C(C(C(N)=O)=C(O)[C@H]4N(C)C)=O)([H])OC3=O)=C2C
InChi Code
InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)20(32-22(12)31)13-15(24(2)3)17(27)14(21(23)30)19(29)18(13)28/h4-6,13,15,18,20,25-28H,1-3H3,(H2,23,30)/t13-,15-,18+,20-/m0/s1
InChi Key
DRKMHDAKULCOKQ-VPZFNDQJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    β-Apooxytetracycline is a potential impurity found in commercial preparations of oxytetracycline.1 β-Apooxytetracycline is a degradation product formed from oxytetracycline (Item No. 18076) 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.2 β-Apooxytetracycline (10 mg/kg) is toxic to rats, decreasing body weight, disrupting blood cell counts, and inducing hepatocyte necrosis.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lykkberg, A.K., Halling-Sørensen, B., Cornett, C., et al. Quantitative analysis of oxytetracycline and its impurities by LC-MS-MS. J. Pharm. Biomed. Anal. 34(2), 325-332 (2004).

    2. Halling-Sørensen, B., Sengeløv, G., and Tjørnelund, J. Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacteria, including selected tetracycline-resistant bacteria. Arch. Environ. Contam. Toxicol. 42(3), 263-271 (2002).

    3. Hue, N.V., Toan, N.V., Long, L.T., et al. Preliminary studies on the toxic effects of degradation products of oxytetracycline and chlortetracycline on rats. J. Ag. Sci. Technol. A. B. 5, 469-474 (2015).