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Ionization and partitioning profiles of zwitterions: The case of the anti-inflammatory drug azapropazone

Caron, Giulia
Pagliara, Alessandra
Gaillard, Patrick
Testa, Bernard
Published in Helvetica Chimica Acta. 1996, vol. 79, no. 6, p. 1683-1695
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 equilibria, 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 pK(al), 1 exists in the physiological pH range as a zwitterion and as an anion. Some pharmacological implications of these findings are discussed
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Deposited on : 2010-08-06

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