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- Title
Ionization and Partitioning Profiles of Zwitterions: The case of the anti-inflammatory drug azapropazone.
- Authors
Caron, Giulia; Pagliara, Alessandra; Gaillard, Patrick; Carrupt, Pierre-Alain; Testa, Bernard
- Abstract
Azapropazone ( 1) is a non-steroidal anti-inflammatory drug (NSAID) whose chemical structure is markedly different from that of other agents in this class and challenges our understanding of structure-activity and structure-permeation relationships. Using a variety of experimental and computational techniques, we studied 1 for its molecular structure in the gas phase and non-protic polar solvents, protonation/deprotonation equilibra, tautomerism, and pH-lipophilicity profiles (octan-1-ol/H2O and dodecane/H2O). Other NSAIDs and model compounds were also examined for comparison. Due to its very low acidic p Ka1, 1 exists in the physiological pH range as a zwitterion and as an anion. Some pharmacological implications of these findings are discussed.
- Publication
Helvetica Chimica Acta, 1996, Vol 79, Issue 6, p1683
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19960790618