Journal of Pharmaceutical Sciences p. 1004 - 1009 (1977)
Update date:2022-08-12
Topics:
Tsuji
Itatani
Yamana
Methods were developed for quantitating epimerization to epihetacillin and hydrolysis to ampicillin in the alkaline degradation of hetacillin, and both rates in deuterium oxide at 35° and in water at various temperatures were determined. In each case, plots of log k for the epimerization against pH or pD yielded straight lines with a positive slope, which verified the first-order dependence on the hydroxide ion or deuteroxide ion. The activation energy of the epimerization process was 21.2 kcal/mole. In aqueous solution at high pH, epimerization rather than conversion to ampicillin represents a major pathway of hetacillin degradation, although the β-lactam ring of the hetacillin molecule is highly resistant to attack by the hydroxide ion.
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