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Characterization of an Unknown Impurity in Glucosamine Sulfate Sodium Chloride by HPLC-Q-TOF MS and NMR

Author(s):

Miao Zhang, Peixi Zhu, Yue Chen, Weifang Ni, Yu Li* and Liya Hong*   Pages 1 - 11 ( 11 )

Abstract:


Background: Glucosamine sulfate sodium chloride (glucosamine-SP) is mainly used for the treatment of osteoarthritis. During quality control of glucosamine-SP capsules, an unknown impurity was detected. Another unknown degradation product was generated together with above-mentioned impurity in heat condition.

Objective: The study aimed to characterize an unknown impurity in glucosamine-SP capsules.

Method and Results: A new volatile HPLC method compatible with mass spectrometry detection was set up. An amino column at 35 °C with a mobile phase consisting of water and acetonitrile (20: 80, v/v) was used at a flow rate of 1.5 ml/min at 297 nm. High-performance liquid chromatography quadrupole time-of-flight mass spectrometry (HPLC-Q-TOF MS) was used to identify the impurity with the electrospray ionization (ESI) source in the positive ionization mode. The results of HPLC-Q-TOF MS analysis indicated that the protonated molecule ions [M + H]+ of the unknown impurity and the novel degradation product were both at m/z 287. Preparative LC method was put into practice with a Prep-C18 column with a mobile phase consisting of water and acetonitrile (99: 1, v/v) at a flow rate of 20.0 ml/min at 297 nm. The assignment of the 1D and 2D NMR signals was performed for the unknown impurity. In addition, the formation of impurities was also studied.

Conclusion: An unknown impurity and a degradation product in glucosamine-SP capsules were characterized. They were assigned as (1R, 2S, 3R)-1-(5-((S, E)-3, 4-dihydroxybut-1-en-1-yl) pyrazin-2-yl) butane-1, 2, 3, 4-tetraol and (1R, 2S, 3R)-1-(5-((S, Z)-3, 4-dihydroxybut-1-en-1-yl) pyrazin-2-yl) butane- 1, 2, 3, 4-tetraol.

Keywords:

glucosamine sulfate sodium chloride, HPLC-Q-TOF mass spectrometry, unknown impurity, degradation product, preparative liquid chromatography, nuclear magnetic resonance (NMR)

Affiliation:

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, P. R., College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, 310014, P. R., Zhejiang Institute for Food and Drug Control, Hangzhou, 310052, P. R., Zhejiang Institute for Food and Drug Control, Hangzhou, 310052, P. R., Zhejiang Institute for Food and Drug Control, Hangzhou, 310052, P. R., College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, P. R.



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