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Characterization of two cyclic metabolites of sitagliptin

Liu, David Q ; Arison, Byron H ; Stearns, Ralph A ; Kim, Dooseop ; Vincent, Stella H

Drug metabolism and disposition: the biological fate of chemicals, April 2007, Vol.35(4), pp.521-4 [Peer Reviewed Journal]

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  • Title:
    Characterization of two cyclic metabolites of sitagliptin
  • Author: Liu, David Q ; Arison, Byron H ; Stearns, Ralph A ; Kim, Dooseop ; Vincent, Stella H
  • Description: Two novel metabolites of the dipeptidyl peptidase inhibitor sitagliptin (MK-0431, (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)-butan-2-amine), were identified after purification from dog urine. The metabolites (referred to as M2 and M5) were characterized by hydrogen/deuterium exchange tandem mass spectrometry and NMR spectroscopy nuclear Overhauser effect experiments as the cis and trans stereoisomers formed by cyclization of the primary amino group with the alpha carbon of the piperazine ring, following oxidative desaturation.
  • Is Part Of: Drug metabolism and disposition: the biological fate of chemicals, April 2007, Vol.35(4), pp.521-4
  • Identifier: ISSN: 0090-9556 ; PMID: 17220240 Version:1
  • Subjects: Enzyme Inhibitors -- Metabolism ; Hypoglycemic Agents -- Metabolism ; Pyrazines -- Metabolism ; Triazoles -- Metabolism
  • Language: English
  • Source: MEDLINE/PubMed (U.S. National Library of Medicine)

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