Studies on beta-lactam antibiotics for medicinal purpose. III. Structure-activity relationship of 6-[D (-) -alpha- (4-alkyl-2,3-dioxo-1-piperazinecarbox-amido) phenylacetamido]penicillanic acids

Saikawa, I.; Yasuda, T.; Taki, H.; Tai, M.; Watanabe, Y.

Yakugaku Zasshi Journal of the Pharmaceutical Society of Japan 97(9): 987-994


ISSN/ISBN: 0031-6903
PMID: 200728
Accession: 068523837

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Structure-activity relationship of new semisynthetic penicillins, 6-[D(-)-.alpha.-(4-alkyl-2,3-dioxo-1-piperazinecarboxamido)phenylacetamido]penicillanic acid (I) was investigated. In in vitro antibacterial activity against clinically isolated strains of Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Serratia marcescens, Proteus mirabilis, P. vulgaris, P. morganii, P. rettgeri and Pseudomonas aeruginosa, structure-activity relationship was recognized, except in P. aeruginosa, and antibacterial activity became stronger with the increase in C number of the alkyl group in I. Such a tendency was especially marked against K. pneumoniae and S. marcescens. Stability against .beta.-lactamase, blood level, protein binding, acute toxicity and distribution coefficient of I were all related to the number of C atoms in the alkyl group of I. In protective effect against esperimental infection in mice, T-1220 (I: R = (C2H5) was the most effective and more effective than carbenicillin against P. aeruginosa infection.