Synthesis of 5-azacytidine-6-13C and -6-14C

J Med Chem. 1977 Apr;20(4):598-600. doi: 10.1021/jm00214a034.

Abstract

5-Azacytidine (1) labeled with 13C or 14C at the chemically labile C-6 position was synthesized. A method utilizing hydrolytic opening of the triazine ring followed by recyclization with dimethylformamide dimethyl acetal was used. Urinary and biliary excretion was measured in rabbits following intravenous doses of 1-4-14C and 1-6-14C. Differences in recoveries of the dose from 4-14C and 6-14C demonstrate that ring cleavage of 1 with loss of the C-6 carbon represents a major metabolite route.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Azacitidine / chemical synthesis*
  • Azacitidine / metabolism
  • Azacitidine / urine
  • Bile / metabolism
  • Carbon Isotopes*
  • Carbon Radioisotopes*
  • Isotope Labeling*
  • Male
  • Methods
  • Rabbits

Substances

  • Carbon Isotopes
  • Carbon Radioisotopes
  • Azacitidine