Carbenicillin prodrugs: Kinetics of intestinal absorption competing degradation of the α‐esters of carbenicillin and prediction of prodrug absorbability from quantitative structure‐absorption rate relationship

Akira Tsuji, Tetsuya Terasaki, Etsuko Miyamoto, Tsukinaka Yamana

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The intestinal absorption of α‐esters of carbenicillin disodium, carbenicillin phenyl sodium, and carbenicillin indanyl sodium was investigated using the in situ rat intestinal recirculating method. In the in situ intestinal lumen at pH 7, two prodrugs were rapidly converted to poorly absorbable carbenicillin, possibly by the action of intestinal nonspecific esterase in competition with the slow absorption of prodrugs. At pH 5, the reduced action of esterase and the increased absorption rate after 3 hr resulted in 50 and 60% absorption of carbenicillin phenyl sodium and carbenicillin indanyl sodium, respectively. The absorption rate constants determined for both prodrugs were in good agreement with the prediction from the quantitative structure‐absorption rate relationship derived from the two‐compartment aqueous diffusion model.

Original languageEnglish
Pages (from-to)403-406
Number of pages4
JournalJournal of Pharmaceutical Sciences
Volume71
Issue number4
DOIs
Publication statusPublished - 1982 Jan 1
Externally publishedYes

Keywords

  • Absorption, intestinal—carbenicillin prodrugs, kinetics
  • Carbenicillin—prodrugs, kinetics of intestinal absorption, α‐esters
  • Prodrugs—carbenicillin, kinetics of intestinal absorption, α‐esters

ASJC Scopus subject areas

  • Pharmaceutical Science

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