GC-MS validation of the organic ionic impurity tetra-n-butylammonium bromide in Teneligliptin

Murugan Maniavannan; Paramasivam Parthiban; Palaniappan Ilayaraja; Jagatheesan Rathinavel

doi:10.7324/JAPS.2023.50530

Abstract

Teneligliptin is a potential drug to control type 2 diabetes but during the synthesis of Teneligliptin, the tetra-n-butylammonium bromide (TBAB) is used as a phase transfer catalyst, and thus it reaches the drug as an impurity. The existing analytical methods for the determination of TBAB in drugs are very limited, particularly with no effective GC method. Thus, the new method developed and optimized on Agilent 5977B GC/MSD equipped with DB-1 capillary column (60 m × 0.32 mm × 0.25 μm) using helium as carrier gas. Detection was performed at the m/z of 100, 142, and 185 using selective ion monitoring mode. The concentration range of 1.0–1,500 ppm with a correlation coefficient of 0.9971 was determined by the linearity curve. The detection (LOD) and quantitation limits (LOQ) of TBAB were 0.3 and 1.0 μg/g concerning the sample weight. The average recovery of TBAB was 97.8%, indicating the method is accurate, and the RSD area of the six replicates injection of TBAB standard was <5%, indicating good precision. Thus, the proposed method showed excellent linearity, accuracy, precision, specificity, LOD, LOQ, and system suitability according to the ICH guidelines. Finally, the method’s suitability was proved with commercial batches, which is an essential step to demonstrate the applicability and practicality of the method.

Keyword: Tetra-n-butylammonium bromide TBAB teneligliptin GC-MS validation

Citation:

Manivannan M, Parthiban P, Ilayaraja P, Jagatheesan R. GC-MS validation of the organic ionic impurity tetra-n-butylammonium bromide in Teneligliptin. J Appl Pharm Sci, 2023. https://doi.org/10.7324/JAPS.2023.50530

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Reference

Chang, JS, Abu-Orf M, Dentel, SK. Alkylamine odors from degradation of flocculant polymers in sludges. Water Res. 2005;39:3369-75.https://doi.org/10.1016/j.watres.2005.05.047

Christian B, Johannes R, Detlef J. Simultaneous determination of tetrabutylammonium and tributylamine in wastewater byIC/LC-MS. ThermoFischer Scientific Technical Report, 2020; DOI: 10.13140/ RG.2.2.29215.10402

European Medicines Agency ICH Topic Q 2 (R1). Note for guidance on validation of analytical procedures text and methodology. 1995;CPMP/ICH/381/95.

Fernanda NF, Julio CA, Fernanda VMP, Manuel CC, Arnaldo AN, Rainério EJ, Maria ICM, Ultrasound-assisted purge-and-trap extraction for simultaneous determination of low-molecular weight amines and ammonium in high salinity waters by ion chromatography. Microchem J, 2017;133:658-62.https://doi.org/10.1016/j.microc.2017.03.006

Fernando PN, Egwu IN, Hussain MS. Ion chromatographic determination of trace hydroxylamine in waste streams generated by a pharmaceutical reaction process. J Chromatogr A. 2002;956:149-55.https://doi.org/10.1016/S0021-9673(02)00145-0

Hajos P, Horvath K, Conca R, Sarzanini C. Histidine as a dipolar eluent in ion chromatography of aliphatic amines. Chromatographia, 2002;56:S103-6.https://doi.org/10.1007/BF02494121

Hall RE, Havner GD, Good R, Dunn DL. Ion chromatographic method for rapid and quantitative determination of trimethylamine. J Chromatogr A, 1995;718:305-8.https://doi.org/10.1016/0021-9673(95)00699-0

Hao F, Lwin T, Bruckard WJ, Woodcock JT. Determination of aliphatic amines in mineral flotation liquors and reagents by high-performance liquid chromatography after derivatisation with 4-chloro-7- nitrobenzofurazan. J Chromatogr A. 2004; 1055:77-85.https://doi.org/10.1016/j.chroma.2004.08.130

Herraez-Hernandez R, Chafer-Pericas C, Verdu-Andres J, Campins-Falco P. An evaluation of solid phase microextraction for aliphatic amines using derivatization with 9-fluorenylmethyl chloroformate and liquid chromatography. J Chromatogr A, 2006; 1104:40-6.https://doi.org/10.1016/j.chroma.2005.11.121

ICH Q3C (R5): Technical requirements for registration of pharmaceuticals for human use impurities guideline for residual solvents. In: international Conference on Harmonization, 2011.https://www.pmda. go.jp/files/000156308.pdf

Jagota NK, Chetram AJ, Nair JB. Ion chromatography of amylamine and tert-butylamine in pharmaceuticals. J Chromatogr A, 1996;739:343-9.https://doi.org/10.1016/0021-9673(96)00046-5

Jerome V, Hermann M, Hilbrig F, Freitag, R. A fast method for the quantification of methylamine in fermentation broths by gas chromatography. J Chromatogr B, 2008;861:88-94.https://doi.org/10.1016/j.jchromb.2007.11.027

Kadnar R. Determination of amines used in the oil and gas industry (upstream section) by ion chromatography. J Chromatogr A, 1999;850:289-95.https://doi.org/10.1016/S0021-9673(99)00623-8

Kishimoto M. Teneligliptin: a DPP-4 inhibitor for the treatment of type 2 diabetes. Diabetes Metab Syndr Obes: targets Therapy, 2013;6:187-95.https://doi.org/10.2147/DMSO.S35682

Krol J, Alden PG, Morawski J, Jackson PE. Ion chromatography of alkylamines and alkanolamines using conductivity detection. J Chromatogr A, 1992;626:165-70.https://doi.org/10.1016/0021-9673(92)85406-J

Kumagai H, Shimizu N, Shimomura Y, Sakai T, Inoue Y. Retention behavior of methylamines ethylenediamine and N-methylsubstituted ethylenediamines on a cation-exchange resin having a polycarboxylic acid as the functional group. J Chromatogr A. 1996;739:327-31.https://doi.org/10.1016/0021-9673(96)00248-8

Lopez AF, de Ariza MTP, Orio OA. Rapid method for quantitative determination of tetrabutylammonium bromide in aqueous solution by gas chromatography. J High Resolut Chrom, 1988;12:503-4.https://doi.org/10.1002/jhrc.1240120725

Maryam A, Bahman F, Mehdi V, Akbar Z, Application of cation-exchange chromatography for quantification of some ethanolamine degradation products in the natural gas sweetening solution. J Taiwan Inst Chem Eng, 2021;127:69-78.https://doi.org/10.1016/j.jtice.2021.08.009

Meseguer-Lloret S, Molins-Legua C, Verdu-Andres J, Campins- Falco P. Sensitive determination of aliphatic amines in water by high-performance liquid chromatography with chemiluminescence detection. J Chromatogr A. 2004;1035:75-82.https://doi.org/10.1016/j.chroma.2004.02.027

Reddy, YS. Analytical method validation for the determination of tetrabutlylammonium bromide content in Daclatasvir dichloride by LC/ MS/MS. J Global Pharma Tech. 2019; 11(1):15-21.

Sharma SK, Panneerselvam A, Singh KP, Parmar G, Gadge P, Swami O. Teneligliptin in management of type 2 diabetes mellitus. Diabetes Metab Syndr Obes: targets Therapy. 2016;9:251-6.https://doi.org/10.2147/DMSO.S106133

Subramanian NH, Manigandan P, Ganesh JR, Radhakrishnan G. Ion chromatographic determination of residual phase transfer catalyst in active pharmaceutical ingredient. J Chromatogr Sci. 2009;47:540-4.https://doi.org/10.1093/chromsci/47.7.540

Tan HSI, Xu J, Zheng Y. Cation-exchange high-performance liquid chromatographic assay of piperazine in some pharmaceutical formulations. J Chromatogr A. 1995;693:307-14.https://doi.org/10.1016/0021-9673(94)01040-L

The European Agency for the Evaluation of Medicinal Products ICH topic Q 2 B. Note for Guidance on Validation of Analytical Procedures Text and Methodology. 1997;CPMP/ICH/281/95.

United States Pharmacopoeia. General Chapter, Residual Solvents, 2016; USP39-NF34:339.

Zhao YY, Jing ZZ, Wang H, Zhang HS, Yu JX. N-Hydroxysuccinimidylphenylacetate as a novel derivatizing reagent for aliphatic amines in gas chromatography. Anal Chim Acta. 2003;468:255-61https://doi.org/10.1016/S0003-2670(02)00689-X

Abstract

HTML Full Text

Reference

Article Metrics

Related Search

Citiaion Alert By Google Scholar

Similar Articles