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Hydrolysis and Epimerization Kinetics of Hetacillin in Aqueous Solution

Hydrolysis and Epimerization Kinetics of Hetacillin in Aqueous Solution

A Tsuji, Y Itatani, T Yamana

J Pharm Sci. 1977 Jul;66(7):1004-9.

PMID: 18591

Abstract:

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 degrees 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 beta-lactam ring of the hetacillin molecule is highly resistant to attack by the hydroxide ion.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP12168308	Ammonium-d4 deuteroxide solution		12168-30-8	Price

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