Antibiotic resistance is prevalent in today's society. Clavulanic acid (CA), a β-lactamase inhibitor, is co-administered with amoxicillin to combat antibiotic resistance, so it is of significant industrial and clinical importance. Some of the CA, which is produced via fermentation and extracted as potassium clavulanate, is degraded (owing to its strained ring structure) during the multi-step manufacturing process (Figure 1). To optimize its synthesis, the degradation of potassium clavulanate under various pH and temperature conditions was monitored using stopped-flow UV-vis spectrophotometry and the results were compared to previous degradation data collected via HPLC. The resulting UV-vis rate constants were lower than the rate constants obtained using HPLC. Furthermore, extraction conditions from specific stages of the manufacturing process were mimicked. The aim was to monitor the degradation of potassium clavulanate using stopped-flow UV-vis and 1H NMR spectroscopy to identify potential hazards that could occur through a loss of process control on the manufacturing scale. The effect of CA concentration, pH, and temperature on the rate of potassium clavulanate degradation were monitored. The degradation rate constants were found to increase with increasing temperature and acid concentration.

Monitoring the degradation of potassium clavulanate using stopped-flow UV/Vis spectrophotometry

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.