Publication: Identification of an isomer impurity in piperaquine drug substance
Issued Date
2006-12-01
Resource Type
ISSN
00219673
Other identifier(s)
2-s2.0-33750611489
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Chromatography A. Vol.1135, No.2 (2006), 166-169
Suggested Citation
N. Lindegårdh, F. Giorgi, B. Galletti, M. Di Mattia, M. Quaglia, D. Carnevale, N. J. White, A. Mazzanti, N. P.J. Day Identification of an isomer impurity in piperaquine drug substance. Journal of Chromatography A. Vol.1135, No.2 (2006), 166-169. doi:10.1016/j.chroma.2006.09.066 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/22942
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Title
Identification of an isomer impurity in piperaquine drug substance
Abstract
A significant contaminant of the antimalarial drug piperaquine (1,3-bis-[4-(7-chloroquinolyl-4)-piperazinyl-1]propane) has been identified using liquid chromatography-mass spectrometry (LC-MS) and 2D NMR spectroscopy (1H-1H COSY,1H-13C HSQC,1H-13C HMBC). The impurity was identified as the positional isomer 1-[(5-chloroquinolin-4)-piperazinyl]-3-[(7-chloroquinolin-4)-piperazinyl]propane. The impurity is formed because of contamination of batches of 4,7-dichloroquinoline (a precursor in the synthesis of piperaquine) with 4,5-dichloroquinoline. The amount of impurity (peak area impurity/peak area piperaquine using LC-UV at 347 nm) in old batches of piperaquine and in Artekin (the combination of dihydroartemisinin-piperaquine) ranged from 1.5 to 5%. © 2006 Elsevier B.V. All rights reserved.