Chemjobber: #BadBosutinib: It's not paranoid if the molecules are really out to get you

Bosutinib, also known as SKI-606, is currently in Phase III clinical trials to treat chronic myeloid leukemia. Officials at Pfizer, the company sponsoring the clinical trials, say that only genuine bosutinib has been administered to patients. However, as a selective kinase inhibitor, the compound is also used in medical and basic research. The news that researchers may have unwittingly been using an isomer of bosutinib instead of using the genuine compound threatens to invalidate research efforts around the world….

Levinson and Boxer put their publication on hold, ordered bosutinib from a different vendor, and did a battery of tests to determine which material was the genuine bosutinib. They soon figured out the original compound they had done all their research on turned out not to be bosutinib. “We had wasted a huge amount of time and money on the wrong isomer,” Boxer says. On the basis of multidimensional nuclear magnetic resonance (NMR) experiments, Boxer and Levinson believe that this isomer not only has a chlorine at the 3-position rather than the 2-position, but also that the chloro and methoxy groups that appear in the 4- and 5-positions, respectively, in bosutinib’s aniline moiety have been switched.

OOOOF that is baaaaaaad.