Aqueous Acidic Degradation of the Carbacephalosporin Loracarbef

□ 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...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1993-10, Vol.82 (10), p.1010-1017
Main Authors: Skibic, Michael J., Taylor, K.Wayne, Occolowitz, John L., Collins, Monte W., Paschal, John W., Lorenz, Leslie J., Spangle, Larry A., Dorman, Douglas E., Baertschi, Steven W.
Format: Article
Language:English
Subjects:
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Cefaclor - chemistry
Cephalosporins - chemistry
Chromatography, High Pressure Liquid
Drug Stability
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Solutions - chemistry
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Summary:□ 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.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600821002