Structural Investigation of New Metabolites of Aminopenicillins excreted in Human Urine

概要

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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 HgCl_2 solution or in NaH_2PO_4 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.
公益社団法人日本薬学会の論文
1980-12-25