Research Articles
Aqueous Acidic Degradation of the Carbacephalosporin Loracarbef

https://doi.org/10.1002/jps.2600821002Get rights and content

Abstract

□ The aqueous degradation of the carbacephalosporin loracarbef under moderately acidic conditions (pH range, 2.7 – 4.3) is described. Structures of a total of 10 compounds isolated by preparative reversed-phase HPLC have been proposed. Five of these 10 degradation compounds arose from hydrolysis of the /3-lactam ring followed by structural changes in the six-membered heterocyclic ring. Four compounds form from intermolecular reactions of loracarbef to form dimeric structures with peptide linkages. The remaining compound resulted from oxidation of the primary amine to a hydroxylamine. Pathways for the formation of these compounds from the parent loracarbef are proposed.

References (20)

  • JackmanL.M. et al.
  • PasiniC.E. et al.

    Pharm. Res

    (1992)
  • BlaszczakL.C. et al.

    J. Med. Chem.

    (1990)
  • HirataT. et al.GrayG. et al.QuayJ.F. et al.MatsukumaI. et al.

    Chem. Pharm. Bull

    (1989)
  • HafkemeyerP. et al.

    Nucl. Acids Res

    (1991)
  • DoddrellD.M. et al.

    Magn. Reson

    (1982)
  • MartinG.E. et al.

    Magn. Reson. Chem

    (1988)
  • DeromeA.E.
  • ElielE.L.
There are more references available in the full text version of this article.

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