Methanesulfonate is a good leaving group because of the efficient delocalization of negative charge between three oxygen atoms. For this reason, several compounds containing two methanesulfonate groups separated by a polymethylene chain were tested as antitumor agents, finding that the optimal activity corresponded to the compound with four carbon atoms (busulfan). Other members of this family are piposulfan, improsulfan, hepsulfam, and the previously mentioned diepoxide prodrug treosulfan.

Busulfan is used in the treatment of chronic granulocytic leukemia and, in high-dose combination with cyclophosphamide, to condition patients for alloge-neic bone marrow transplantation. It is particularly toxic for pulmonary tissue, and this toxicity may be dose-limiting.

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