TY - JOUR
T1 - Thermal degradation of amorphous glibenclamide
AU - Rehder, Sönke
AU - Sakmann, Albrecht
AU - Rades, Thomas
AU - Leopold, Claudia S.
PY - 2012/1
Y1 - 2012/1
N2 - A glibenclamide polymorph published by Panagopoulou-Kaplani and Malamataris (2000) [1], obtained by sublimation of amorphous glibenclamide, was analysed. A new interpretation of the data is presented and experimentally confirmed by X-ray powder diffractometry, Fourier transformation infrared spectroscopy, differential scanning calorimetry, and mass spectrometry. The crystals formed during sublimation of amorphous glibenclamide do not represent a glibenclamide polymorph, but a thermal degradation product, namely 1,3-dicyclohexylurea. The reaction mechanism is suggested to be an elimination of cyclohexylisocyanate from glibenclamide. Cyclohexylisocyanate may decompose to carbon monoxide and cyclohexylamine, which may react in an addition reaction with another cyclohexylisocyanate molecule forming 1,3-dicyclohexylurea.
AB - A glibenclamide polymorph published by Panagopoulou-Kaplani and Malamataris (2000) [1], obtained by sublimation of amorphous glibenclamide, was analysed. A new interpretation of the data is presented and experimentally confirmed by X-ray powder diffractometry, Fourier transformation infrared spectroscopy, differential scanning calorimetry, and mass spectrometry. The crystals formed during sublimation of amorphous glibenclamide do not represent a glibenclamide polymorph, but a thermal degradation product, namely 1,3-dicyclohexylurea. The reaction mechanism is suggested to be an elimination of cyclohexylisocyanate from glibenclamide. Cyclohexylisocyanate may decompose to carbon monoxide and cyclohexylamine, which may react in an addition reaction with another cyclohexylisocyanate molecule forming 1,3-dicyclohexylurea.
KW - 1,3-Dicyclohexylurea
KW - Amorphous
KW - Glibenclamide
KW - Polymorphism
KW - Thermal degradation
UR - http://www.scopus.com/inward/record.url?scp=83955161729&partnerID=8YFLogxK
U2 - 10.1016/j.ejpb.2011.07.009
DO - 10.1016/j.ejpb.2011.07.009
M3 - Journal article
C2 - 21907802
AN - SCOPUS:83955161729
VL - 80
SP - 203
EP - 208
JO - European Journal of Pharmaceutics and Biopharmaceutics
JF - European Journal of Pharmaceutics and Biopharmaceutics
SN - 0939-6411
IS - 1
ER -