O

In contrast with nitrogen mustards, where the rate-limiting step is the unim-olecular formation of the aziridinium ion, busulfan reacts with guanine N-7 by an SN2 mechanism (Fig. 5.23), where the rate-limiting step depends on the concentration of both reaction partners.42 The formation of interstrand DNA cross-links has been demonstrated for busulfan43 and treosulfan.44

The study of metabolites of busulfan suggests that it is also able to alkylate cysteine residues. Thus, the urinary excretion of compound 5.32 can be explained by the mechanism summarized in Fig. 5.24 and involves a double nucleophilic attack by cysteine.

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