Identification of an isomer impurity in piperaquine drug substance

descriptionPublicationkeyboard_double_arrow_right Article 01 Dec 2006 United Kingdom, Italy English Publisher:Elsevier BVJournal:Journal of Chromatography A, volume 1,135, pages 166-169 (issn: 0021-9673,

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Authors: N. Lindegårdh; F. Giorgi; B. Galletti; M. Di Mattia; M. Quaglia; D. Carnevale; N. J. White; +2 Authors

doi: 10.1016/j.chroma.2006.09.066

pmid: 17046006

handle: 11585/34106

Identification of an isomer impurity in piperaquine drug substance

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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%.

Countries

United Kingdom, Italy

Related Organizations

Alma Mater Studiorum University of Bologna
Italy
Mahidol University
Thailand
University of Oxford
United Kingdom
Sigma-Tau (Switzerland)
Switzerland

Keywords

Antimalarials, Magnetic Resonance Spectroscopy, Isomerism, HPLC SEPARATION; BI-DIMENSIONAL NMR; ANTIMALARIAN DRUG; DIHYDROARTEMISININ, Quinolines, Spectrophotometry, Ultraviolet, Piperazines, Chromatography, Liquid

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