Photodegradation of oxytocin and thermal stability of photoproducts

J Pharm Sci. 2012 Sep;101(9):3331-46. doi: 10.1002/jps.23204. Epub 2012 May 23.

Abstract

Photodegradation of oxytocin at λ = 253.7 nm and λ ≥ 290 nm results in the transformation of the intrachain disulfide bond into predominantly dithiohemiacetal and thioether. Especially the dithiohemiacetal is sensitive to further degradation by light and/or elevated temperature, implying that the combination of an initial photostress and a subsequent heat stress can yield products significantly different compared with those observed under heat stress only.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Disulfides / chemistry
  • Disulfides / radiation effects*
  • Drug Stability
  • Hydrogen-Ion Concentration
  • Models, Chemical
  • Oxidation-Reduction
  • Oxytocics / chemistry
  • Oxytocics / radiation effects*
  • Oxytocin / chemistry
  • Oxytocin / radiation effects*
  • Photolysis*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet
  • Tandem Mass Spectrometry
  • Technology, Pharmaceutical / methods
  • Temperature*
  • Ultraviolet Rays*

Substances

  • Disulfides
  • Oxytocics
  • Oxytocin