Preparation of D-phenylglycinyl derivatives of cefuroxime as double ester prodrugs

Jia Shuai Lee, Chi Hua Sun, Hui Po Wang*

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

3 Scopus citations

Abstract

D-Phenylglycine was attached at the 4-COOH of cefuroxime via an ethylidene linkage to form double ester derivatives 1a and 1b. The D-phenylglycine moiety was considered as a tool for delivering the poorly absorbed cefuroxime through the intestine. The Δ3 → Δ2 isomerization commonly reported along the preparation of cephalosporin esters was successfully eliminated by adding TBA+HSO4- as phase transfer catalyst in the alkylation reaction. The prodrugs were stable in acidic phosphate buffer solutions, but degraded fairly rapidly in pH 7.39 phosphate buffer solution and in rat intestinal mucosa suspension. The t( 1/4 ) for 1a and 1b were 10 min and 5 min respectively, indicating that both compounds fail to demonstrate satisfactory stability for fomulation as oral prodrugs of cefuroxime.

Original languageEnglish
Pages (from-to)195-205
Number of pages11
JournalChinese Pharmaceutical Journal
Volume49
Issue number3
StatePublished - 06 1997
Externally publishedYes

Keywords

  • Cefuroxime prodrugs
  • D-Phenylglycine

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