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Identification and Physicochemical Characteristics of Temozolomide Process-Related Impurities
Pharmaceutical Research Institute (PRI), Warszawa 01-793, Poland
Faculty of Chemistry, University of Warsaw, Warszawa 02-093, Poland
* Author to whom correspondence should be addressed.
Received: 24 October 2013; in revised form: 27 November 2013 / Accepted: 3 December 2013 / Published: 11 December 2013
Abstract: In this article the crystal structures of the starting material TZ-5 and the key intermediate TZ-6 of temozolomide (TZ-7), an anticancer therapeutic agent, are presented, together with their spectroscopic and thermal characteristics. Both compounds crystallize in the triclinic P-1 space group. X-ray crystallography studies proved that the compound TZ-6 exists as a monohydrate. A complete structural assignment was obtained for the signals in the 1H-, 13C- and 15N-nuclear magnetic resonance spectra and the structures were confirmed by Fourier-Transform infrared and Raman spectroscopy. The article describes the importance of the high purity of TZ-6 during the small-scale plant production of TZ-7 in a desired polymorphic form III with the purity higher than 99.50%, according to an HPLC method.
Keywords: temozolomide intermediate; X-ray crystallography; nuclear magnetic resonance; high-performance liquid chromatography
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Łaszcz, M.; Kubiszewski, M.; Jedynak, Ł.; Kaczmarska, M.; Kaczmarek, Ł.; Łuniewski, W.; Gabarski, K.; Witkowska, A.; Kuziak, K.; Malińska, M. Identification and Physicochemical Characteristics of Temozolomide Process-Related Impurities. Molecules 2013, 18, 15344-15356.
Łaszcz M, Kubiszewski M, Jedynak Ł, Kaczmarska M, Kaczmarek Ł, Łuniewski W, Gabarski K, Witkowska A, Kuziak K, Malińska M. Identification and Physicochemical Characteristics of Temozolomide Process-Related Impurities. Molecules. 2013; 18(12):15344-15356.
Łaszcz, Marta; Kubiszewski, Marek; Jedynak, Łukasz; Kaczmarska, Monika; Kaczmarek, Łukasz; Łuniewski, Wojciech; Gabarski, Krzysztof; Witkowska, Anna; Kuziak, Krzysztof; Malińska, Maura. 2013. "Identification and Physicochemical Characteristics of Temozolomide Process-Related Impurities." Molecules 18, no. 12: 15344-15356.