GSH cleaves AZA to 6MP

Stable Identifier
Reaction [uncertain]
Homo sapiens
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The GST-catalysed cleavage of azathioprine (AZA) to 6-mercaptopurine (6MP) and a nitroimidazol compound (Chalmers 1974) is prevelant at physiological pH (Von Bahr et al. 1980). Spontaneous cleavage is also possible, providing a minor contribution to AZA catabolism. Several groups have shown that biogenic thiols such as glutathione or cysteine can facilitate the first step of AZA activation, due to the presence of carboxyl, thiol, and amine groups in their molecules (Hoffmann et al. 2001, Chrzanowska et al. 2003).
Literature References
PubMed ID Title Journal Year
14714854 Comparative kinetics of azathioprine and metazathioprine mercaptolysis in presence of physiological thiols

Chrzanowska, M, Hermann, T, Kuehn, M, Hałas, A

Acta Pol Pharm 2003
4458670 Studies on the mechanism of formation of 5-mercapto-1-methyl-4-nitroimidazole, a metabolite of the immunosuppressive drug azathioprine

Chalmers, AH

Biochem Pharmacol 1974
7396978 Inhibition of hepatic metabolism of azathioprine by furosemide in human liver in vitro

Gudas, J, von Bahr, C, Glaumann, H, Kaplowitz, N

Biochem Pharmacol 1980
11427067 Mechanism of activation of an immunosuppressive drug: azathioprine. Quantum chemical study on the reaction of azathioprine with cysteine

Hermann, T, Rychlewski, J, Hoffmann, M, Chrzanowska, M

J Am Chem Soc 2001
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