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Abstract
The metabolism of 5-trifluro-2′-deoxythymidine (trifluridine; F3TdR) in male BALB/c mice bearing EMT-6 tumors has been investigated using 19F NMR spectroscopy. We previously (Tandon et al, 1992) reported the detection and identification of 5,6-dihydro-5-trifluorothymine (DHF3T, 3) and 5,6-dihydroxy-5-trifluorothymine (DOHF3T) as new metabolites of F3TdR in mice urine. Further exploration of the metabolism of trifluridine has led to the identification of α-trifluoromethyl-β-ureido-propionic acid (F3MUPA, 4) as a previously unreported metabolite in the urine of F3TdR treated mice. Authentic F3MUPA was obtained by synthesis via an established route. A comparison of chemical shift and the H-F coupling constant of an authentic sample, with the 19F signal from urine, indicated the presence of F3MUPA in murine urine. Mixing crude urine with authentic F3MUPA resulted in the enhancement of the corresponding fluorine signal without affecting or introducing others, thereby confirming the presence of F3MUPA as a urinary metabolite.