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

被引：22

作者：

Caron, G ^{[1
]}

Pagliara, A ^{[1
]}

Gaillard, P ^{[1
]}

Carrupt, PA ^{[1
]}

Testa, B ^{[1
]}

机构：

[1] UNIV LAUSANNE,PHARM SECT,INST CHIM THERAPEUT,CH-1015 LAUSANNE,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1996年 / 79卷 / 06期

关键词：

D O I：

10.1002/hlca.19960790618

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1683 / 1695

页数：13

共 34 条

[1]

Albert A., 1984, DETERMINATION IONIZA

[2] BJERRUM PLOTS FOR THE DETERMINATION OF SYSTEMATIC CONCENTRATION ERRORS IN TITRATION DATA [J].