Cytochrome P450-mediated carbon-carbon bond formation in drug metabolism

Cytochrome P450 (CYPs) enzymes are essential for the metabolism of numerous drug compounds and are capable of catalyzing many types of biotransformation reactions. One of the more unusual reactions catalyzed by CYPs is carbon-carbon (C-C) bond formation, which is critical in organic synthesis but found less commonly in nature. This review focuses on examples of C-C bond formation that occur during drug metabolism and highlights the mechanism for the formation of novel drug metabolites that result from these reactions. The different roles that mammalian CYPs can play in C-C bond formations are also discussed in detail. Ultimately, an understanding of the range of xenobiotics that undergo C-C bond formation and the mechanisms by which they do so can further facilitate metabolite identification and drug design efforts.