title: Hydrolysis of the prodrug, 2',3',5'-triacetyl-6-azauridine.
abstract: OBJECTIVE
  The purposes were to study the kinetics of hydrolysis of 2',3',5'-triacetyl-6-azauridine (1) in aqueous solution (mu = 0.5) and to identify the main intermediates and products of the reaction.
  
  
  METHODS
  A stability indicating isocratic LC assay was used to study the rate of degradation of 1. A gradient LC assay was used to study the time courses of the degradants. The products of hydrolysis were isolated by preparative liquid chromatography and identified by 1H-NMR and CI-MS. The pKa value was obtained by potentiometric titration.
  
  
  RESULTS
  At 36.8 degrees C, the pH-rate profile of 1 in water was adequately described by a four-term rate equation. The intermediates were identified as the primary and secondary di-acetates, and the primary and secondary mono-acetates. The final product was 6-azauridine.
  
  
  CONCLUSIONS
  A simplified kinetic scheme could be used to describe the concentration-time profiles of 1, the intermediates and the final product.
authors.affiliation: Department of Pharmaceutical Chemistry, University of Kansas, Lawrence 66045-2504, USA.
authors.forename: C M
authors.initials: CM
authors.lastname: Riley
authors.forename: M A
authors.initials: MA
authors.lastname: Mummert
authors.forename: J
authors.initials: J
authors.lastname: Zhou
authors.forename: R L
authors.initials: RL
authors.lastname: Schowen
authors.forename: D G
authors.initials: DG
authors.lastname: Vander Velde
authors.forename: M D
authors.initials: MD
authors.lastname: Morton
authors.forename: M
authors.initials: M
authors.lastname: Slavik
mesh_terms: D001380:Azauridine / Q000031:analogs & derivatives* / Q000737:chemistry; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D066298:In Vitro Techniques; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D011355:Prodrugs / Q000737:chemistry*; D012996:Solutions; D013696:Temperature; D013816:Thermodynamics; D014867:Water
chemical_list: D011355:Prodrugs; D012996:Solutions; D014867:Water; D001380:Azauridine; C100231:azaribine