Journal of Pharmaceutical Sciences p. 845 - 847 (1992)
Update date:2022-08-05
Topics:
Hughes
Toth
Ward
McColm
Cox
Anderson
Gibbons
Lipophilic, double-ester derivatives of β-lactam antibiotics with methylene, ethylene, and propylene spacers were prepared by crown-ether- assisted coupling of halogenoalkyl esters of 2-(tert- butoxycarbonylamino)decanoic acid to either penicillin G or cefuroxime. The hydroxyethyl ester of penicillin G and the tert-butoxypropyl ester of cefuroxime were also prepared. The lipophilic, double-ester conjugates, the hydroxyethyl ester of penicillin G, and the tert-butoxypropyl ester of cefuroxime showed weak or no antibiotic activity in vitro, as expected. The lipophilic penicillin G conjugates and the tert-butoxypropyl ester of cefuroxime were active in vivo against a nonpenicillinase-producing strain of Staphylococcus aureus after subcutaneous administration. The penicillin G double ester with propylene spacer and the tert-butoxypropyl ester of cefuroxime were inactive in vitro, a fact indicating that both compounds were hydrolyzed in vivo, as desired. After oral administration, the lipophilic, double-ester conjugate of penicillin G with methylene spacer and the tert- butoxypropyl ester of cefuroxime were active.
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Doi:10.1021/ja00047a076
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