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Studies on prodrugs of cephalosporins. I. Synthesis and biological properties of glycyloxybenzoyloxymethyl and glycylaminobenzoyloxymethyl esters of 7 beta-[2-(2- aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3- methyl-3-cephem-4-carboxylic acid



Studies on prodrugs of cephalosporins. I. Synthesis and biological properties of glycyloxybenzoyloxymethyl and glycylaminobenzoyloxymethyl esters of 7 beta-[2-(2- aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3- methyl-3-cephem-4-carboxylic acid



Chemical and Pharmaceutical Bulletin 32(2): 692-698



p-Glycyloxy-, o-glycylamino- and p-glycylaminobenzoyloxymethyl esters of 7.beta.-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-methyl-3-cephem-4-carboxylic acid (1) were synthesized as prodrugs designed to improve the oral absorption of the parent cephalosporin. The esters possessed the desired factors for an orally active prodrug, i.e., appropriate solubility, lipophilicity and lability. As predicted from these factors, the esters when administered orally to mice were well absorbed from the gastrointestinal tract and gave high blood levels of the parent compuond (1).

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Accession: 044432308

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PMID: 6547372

DOI: 10.1248/cpb.32.692


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