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 language | English |
---|---|
Pages (from-to) | 195-205 |
Number of pages | 11 |
Journal | Chinese Pharmaceutical Journal |
Volume | 49 |
Issue number | 3 |
State | Published - 06 1997 |
Externally published | Yes |
Keywords
- Cefuroxime prodrugs
- D-Phenylglycine