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. Author manuscript; available in PMC: 2018 Mar 27.
Published in final edited form as: Chem Res Toxicol. 2017 Feb 2;30(2):642–656. doi: 10.1021/acs.chemrestox.6b00385

Figure 2.

Figure 2

Both quinone-forming and nonquinone-forming molecules can undergo comparable initial metabolic events. Nefazodone first undergoes aromatic hydroxylation to form hydroxy-nefazodone, which is then oxidized to form the reactive nefazodone quinone, thereby causing hepatotoxicity in some patients.30,31 In contrast, the analogue buspirone does not form a quinone, despite undergoing a comparable initial hydroxylation event.31 A key goal of our model was to accurately identify molecules that form quinones.