Structural investigation of new metabolites of amino-penicillins excreted in human urine.

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New metabolites have been found in human urine after the oral administration of some amino-penicillins. HPLC analysis showed that the amino-penilicillin metabolite had the same retention time as an in vitro degradation product of the corresponding penicilloic acid in dilute HgCl2 solution or in NaH2PO4 solution. The product was not formed by the same treatment of the intact penicillin. NMR, Raman, and FD mass spectra of the product and the visible absorption spectrum of its colored derivative indicated cleavage of the C-S bond in the thiazolidine ring of the penicilloic acid to leave an SH group. These findings indicate that the metabolite is the penamaldic acid of the parent penicillin. Direct evidence for the presence of the penamaldic acid was obtained from the 200 MHz 1H NMR spectrum of a urine specimen taken after drug administration. Ampicillin and amoxycillin gave metabolites of this kind, but cyclacillin gave no detectable amount of the corresponding metabolite.

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