2-Amino-2-[2-(4-octylphenyl)]-1,3-propanediol (FTY720), also known as Fingolimod, is approved by the Food and Drug Administration (FDA) to treat relapsing episodes of Multiple Sclerosis (MS). FTY720 is a structural analogue of endogenous sphingosine. Once ingested, it undergoes phosphorylation to produce FTY720 phosphate, the biologically active compound. At MS doses (0.5 mg/day), FTY720 phosphate causes a drop in resting heartbeat (bradycardia), which can be lethal. Studies have indicated that higher doses (10 mg/day) are therapeutic for cancer treatment. At these higher doses, there is concern that the chance of a patient experiencing bradycardia may be higher. In an attempt to prevent this potentially lethal side effect, we are interested in modifying FTY720 and using it as a prodrug for cancer treatment. Herein, we have optimized the reaction conditions using 2-Amino-2-methyl-1,3-propanediol (AMPD), a model for FTY720, and are now testing their efficacy for the modification of FTY720.

Modification of FTY720 for use as a prodrug for cancer therapy

249th National Meeting (2015)

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