An inactive alkaline degradation product of chlortetracycline
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Isochlortetracycline

Item No. 22125

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S,4aS,6S,8aS)-6-[(1S)-7-chloro-1,3-dihydro-4-hydroxy-1-methyl-3-oxo-1-isobenzofuranyl]-4-(dimethylamino)-1,4,4a,5,6,7,8,8a-octahydro-3,8a-dihydroxy-1,8-dioxo-2-naphthalenecarboxamide
CAS Number
514-53-4
Synonyms
  • 7-Chloroisotetracycline
  • Isoaureomycin
Molecular Formula
C22H23ClN2O8
Formula Weight
478.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C([C@@](C(C(C(N)=O)=C(O)[C@H]1N(C)C)=O)(O)[C@@]1([H])C2)C[C@@]2([H])[C@]3(C)OC(C4=C3C(Cl)=CC=C4O)=O
InChi Code
InChI=1S/C22H23ClN2O8/c1-21(15-10(23)4-5-11(26)13(15)20(31)33-21)8-6-9-16(25(2)3)17(28)14(19(24)30)18(29)22(9,32)12(27)7-8/h4-5,8-9,16,26,28,32H,6-7H2,1-3H3,(H2,24,30)/t8-,9-,16-,21-,22-/m0/s1
InChi Key
GFSLIMZISCAANG-AXVXPIMKSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Isochlortetracycline is an inactive alkaline degradation product of the broad-spectrum antibiotic chlortetracycline.1,2 This molecule appears to be a product of in vivo chlortetracycline metabolism with epimerization rates exceeding >50%, and high levels can be detected in the yolks of eggs from chickens exposed to this antibiotic.3 Isochlortetracycline is used as a reference standard in chromatographic analyses of chlortetracycline and its metabolic derivatives.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Collett, J.H., Collett, C., Martin, A.N., et al. The effects of some tetracyclines on synchronously growing cultures of Eschericihia coli B/r. J. Pharm. Pharmacol. 22(9), 672-678 (1970).

    2. Diana, J.V., L., De Spiegeleer, B., Hoogmartens, J., et al. Evaluation of the stability of chlortetracycline in granular premixes by monitoring its conversion into degradation products. J. Pharm. Biomed. Anal. 39(3-4), 523-530 (2005).

    3. Zurhelle, G., Petz, M., Mueller-Seitz, E., et al. Metabolites of oxytetracycline, tetracycline, and chlortetracycline and their distribution in egg white, egg yolk, and hen plasma. J. Agric. Food Chem. 48(12), 6392-63936 (2000).