Synthesis and characterization of pregabalin lactose conjugate degradation products.
Seven degradation products observed in formulated pregabalin have been characterized. These compounds result from Maillard reactions and Amadori rearrangements. Heating pregabalin in the presence of lactose formed significant quantities of these degradation products. The seven compounds corresponding to the observed degradation products were isolated by preparative liquid chromatography. The synthesis, isolation, and spectral characterization of the degradation products are detailed.
Lovdahl
Michael J
MJ
Analytical Development Department, Pfizer Global Research and Development, 2800 Plymouth Road, Ann Arbor, MI 48105, USA. michael.lovdahl@pfizer.com
Hurley
Timothy R
TR
Tobias
Brian
B
Priebe
Stephen R
SR
D000927:Anticonvulsants / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D007785:Lactose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000069583:Pregabalin; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D000927:Anticonvulsants; D000069583:Pregabalin; D005680:gamma-Aminobutyric Acid; D007785:Lactose