Stereospecific metabolism of itraconazole by CYP3A4: dioxolane ring scission of azole antifungals.

@article{Peng2012StereospecificMO,
  title={Stereospecific metabolism of itraconazole by CYP3A4: dioxolane ring scission of azole antifungals.},
  author={Chi-Chi Peng and Wei Shi and Justin D. Lutz and Kent L. Kunze and Jun O Liu and W. L. Nelson and Nina Isoherranen},
  journal={Drug metabolism and disposition: the biological fate of chemicals},
  year={2012},
  volume={40 3},
  pages={426-35}
}
Itraconazole (ITZ) is a mixture of four cis-stereoisomers that inhibit CYP3A4 potently and coordinate CYP3A4 heme via the triazole nitrogen. However, (2R,4S,2'R)-ITZ and (2R,4S,2'S)-ITZ also undergo stereoselective sequential metabolism by CYP3A4 at a site distant from the triazole ring to 3'-OH-ITZ, keto-ITZ, and N-desalkyl-ITZ. This stereoselective metabolism demonstrates specific interactions of ITZ within the CYP3A4 active site. To further investigate this process, the binding and… CONTINUE READING
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