Reaction: GSH cleaves AZA to 6MP

- in pathway: Azathioprine ADME
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).
Reaction - small molecule participants:
GS-nitroimidazole [extracellular region]
GSH [extracellular region]
Reactome.org reaction link: R-HSA-9751051

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Reaction input - small molecules:
glutathionate(1-)
ChEBI:57925
Reaction output - small molecules:
GS-nitroimidazole
ChEBI:180931
Reactome.org link: R-HSA-9751051