title: High-performance liquid chromatographic analysis of chemical stability of 5-aza-2'-deoxycytidine.
abstract: The chemical stability of 5-aza-2'-deoxycytidine (I) in acidic, neutral, and alkaline solutions was analyzed by high-performance liquid chromatography. In alkaline solution, I underwent rapid reversible decomposition to N-(formylamidino)-N'-beta-D-2-deoxyribofuranosylurea (II), which decomposed irreversibly to form 1-beta-D-2'-deoxyribofuranosyl-3-guanylurea (III). The pseudo-first-order rate constants for this reaction were determined. The decomposition of I in alkaline solution was identical to that reported previously for the related analog, 5-aza-cytidine. However, in neutral solution (or water), there was a marked difference in the decomposition of I and 5-azacytidine. The same decomposition products were formed from 5-azacytidine in neutral solution as in alkaline solution. However, in neutral solution, I decomposed to II and three unknown compounds that were chromophoric at 254 nm. Compound I was most stable when stored in neutral solution at low temperature.
mesh_terms: D001374:Azacitidine / Q000031:analogs & derivatives* / Q000032:analysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D000077209:Decitabine; D004355:Drug Stability; D007700:Kinetics
chemical_list: D000077209:Decitabine; D001374:Azacitidine