Thermal degradation of amorphous glibenclamide

Sönke Rehder; Albrecht Sakmann; Thomas Rades; Claudia S. Leopold

doi:10.1016/j.ejpb.2011.07.009

Thermal degradation of amorphous glibenclamide

Sönke Rehder, Albrecht Sakmann, Thomas Rades, Claudia S. Leopold^*

^*Corresponding author for this work

Solid State Pharmaceutics

Research output: Contribution to journal › Journal article › Research › peer-review

23 Citations (Scopus)

Abstract

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.

Original language	English
Journal	European Journal of Pharmaceutics and Biopharmaceutics
Volume	80
Issue number	1
Pages (from-to)	203-208
Number of pages	6
ISSN	0939-6411
DOIs	https://doi.org/10.1016/j.ejpb.2011.07.009
Publication status	Published - Jan 2012

Keywords

1,3-Dicyclohexylurea
Amorphous
Glibenclamide
Polymorphism
Thermal degradation

Access to Document

10.1016/j.ejpb.2011.07.009

Cite this

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title = "Thermal degradation of amorphous glibenclamide",

abstract = "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.",

keywords = "1,3-Dicyclohexylurea, Amorphous, Glibenclamide, Polymorphism, Thermal degradation",

author = "S{\"o}nke Rehder and Albrecht Sakmann and Thomas Rades and Leopold, {Claudia S.}",

year = "2012",

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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

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