Recent advances in characterization of impurities - use of hyphenated LC-MS technique

Current Pharmaceutical Analysis

Volumn 6, Issue 4, 2010, Pages 299-306

  Vyas, Vivek K ^a   Ghate, Manjunath ^a   Ukawala, Ravikumar D ^a  

^a NIRMA UNIVERSITY   (India)

Author keywords

Characterization; Hyphenated LC MS; Identification; Impurities; Impurity profiling; LC MS MS; Liquid chromatography mass spectrometry

Indexed keywords

AVERMECTIN; CEFDINIR; CEFTIZOXIME; CITALOPRAM; CLINDAMYCIN PALMITATE; DIACEREIN; EPROSARTAN; EZETIMIBE; FLUCONAZOLE; PANTOPRAZOLE; PIPERACILLIN; PIPERAQUINE; PUERARIN; RIZATRIPTAN; SIMVASTATIN;

DRUG IMPURITY; DRUG POTENCY; DRUG PURITY; DRUG QUALITY; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR WEIGHT; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REVIEW; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY;

EID: 79952752137     PISSN: 15734129     EISSN: None     Source Type: Journal    
DOI: 10.2174/157341210793292392     Document Type: Review

References (63)

1. International Conference on Harmonisation (ICH) Guidelines, Q3A (R): Impurities in New Drug Substances (Revised Guideline), February 2002.
2. International Conference on Harmonisation (ICH) Guidelines, Q3B(R): Impurities in New Drug Products (Revised Guideline), February 2003.
3. International Conference on Harmonisation (ICH) Guidelines, Q3C and Q3C (M): Impurities: Guideline for Residual Solvents, 2002.
4. Ahuja S. Impurities evaluation of pharmaceuticals. Marcel Dekker: New York, 1998.
5. Roy, J. Pharmaceutical impurities - a mini review. AAPS Pharm. Sci. Tech., 2002, 3, 1-8.
6. Schwartz, M.E. Analytical techniques in combinatorial chemistry, Marcel Dekker: New York, 2000.
7. Smith, R.; Webb M. Analysis of drug impurities. Blackwell: Oxford, 2007.
8. Olsen, B.A.; Castle, B.C.; Myers D.P. Advances in HPLC technology for the determination of drug impurities. Trends Anal. Chem., 2006, 25(8), 796-805.
9. Rossi, D.T.; Sinz, M.W. Mass spectrometry in drug discovery. Marcel Dekker: New York, 2002.
10. Szantay C.; Beni, Z.; Balogh, G.; Gati, T. The changing role of NMR spectroscopy in off-line impurity identification: a conceptual view. Trends Anal. Chem., 2006, 25(8), 806-820.
11. Gorog S.; Babjak, M.; Balogh, G.; Brlik, J.; Dravecz, F.; Gazdag, M.; Horvath, P.; Lauko, A.; Varga, K.; Gorog, S. The importance and the challenges of impurity profiling in modern pharmaceutical analysis. Trends Anal. Chem., 2006, 25(8), 755-757.
12. Wu, Y. The use of liquid chromatography-mass spectrometry for the identification of drug degradation products in pharmaceutical formulations. Biomed. Chrom., 2000, 14, 384-396.
13. Gorog S. New safe medicines faster: the role of analytical chemistry. Trends Anal. Chem., 2003, 22, 7-8.
14. Ermer, J. The use of hyphenated LC-MS technique for characterisation of impurity profiles during drug development. J. Pharm. Biomed. Anal., 1998, 18, 707-714.
15. Lim, C.K.; Lord G. Current developments in LC-MS for pharmaceutical analysis. Biol. Pharm. Bull., 2002. 25(5), 547-557.
16. Olsen, B.A.; Castle, B.C.; Myers, D.P. Advances in HPLC technology for the determination of drug impurities. Trends Anal. Chem., 2006, 25(8), 796-805.
17. Hommerson, P.; Khan, A.M.; Bristow, T.; Harrison, M.W.; De Jong, G.J.; Somsen, G.W. Drug impurity profiling by capillary electrophoresis/mass spectrometry using various ionization techniques. Rapid Commun. Mass Spectrom., 2009, 18, 2878-2884.
18. Lurie, I.S.; Bailey, C.G.; Anex, D.S.; Bethea, M.J.; McKibben, T.D.; Casale, J.F. Profiling of impurities in illicit methampheta-mine by high-performance liquid chromatography and capillary electrochromatography. J. Chromatogr. A, 2000, 870(1-2), 53-68.
19. Lee, M.S. LC/MS Applications in drug development. Wiley Inter-Science: New York 2002.
20. Niessen, W.M. Progress in liquid chromatography-mass spectrometry instrumentation and its impact on highthroughput screening. J. Chromatogr. A, 2003, 1000, 413-436.
21. Geoghegan, K.F.; Kelly, M.A. Biochemical applications of mass spectrometry in pharmaceutical drug discovery. Mass Spectrom. Rev., 2005, 24, 347-366.
22. Lim, C.K.; Lord, G. Current developments in LC-MS for pharmaceuticalanalysis. Biol. Pharm. Bull., 2002, 25, 547-557.
23. Lee, M.S.; Kerns, E.H. LC/MS applications in drug development. Mass Spectrom. Rev., 1999, 18, 187-279.
24. Ardrey, R.E. LC-MS: an introduction. Vch Publishing: New York, 2000.
25. Niessen, W.M.A. Liquid chromatography-mass spetroscopy. Marcel Dekker: New York 1998.
26. Nicolas E.C.; Scholz, T.H. Active drug substance impurity profiling part II. LC/MS/MS fingerprinting. J. Pharm. Biomed. Anal., 1998, 16(5), 825-836.
27. Chen G.; Pramanik B.N. Application of LC/MS to proteomics studies: current status and future prospects. Drug Discov. Today, 2009, 14(9-10), 465-471.
28. Asperger, A.; Efer, J.; Koal, T.; Engewald, W. On the signal response of various pesticides in electrospray and atmospheric pressure chemical ionization depending on the flow-rate of eluent applied in liquid chromatography-tandem mass spectrometry. J. Chromatogr. A, 2001, 937, 65-72.
29. Naidong, W.; Chen, Y.; Shou, W.; Jiang, X.; Importance of injection solution composition for LC-MS-MS methods. J. Pharm. Biomed. Anal., 2001, 26, 753-767.
30. Seto, C.; Bateman, K. P.; Gunter, B. Development of generic liquid chromatography-mass spectrometry methods using experimental design. J. Am. Soc. Mass Spectrom., 2002, 13, 2-9.
31. Ermer, J. The use of hyphenated LC-MS technique for characterisation of impurity profiles during drug development. J. Pharm. Biomed. Anal., 1998, 18, 707-714.
32. Wilson I. D.; Nicholson, J. K.; Perez J. C.; Granger J. H.; Johnson K. A.; Smith B. W.; Plumb R. S. High resolution "ultra performance" liquid chromatography coupled to oa-TOF mass spectrometry as a tool for differential metabolic pathway profiling in functional genomic studies. J. Proteome Res., 2005, 4(2), 591-598.
33. Ermer, J.; Vogel, M. Applications of hyphenated LC-MS techniques in pharmaceutical analysis. Biomed. Chromtogr., 2000, 14(6), 373-383.
34. Lee, M.S.; Kerns, E.H. LC/MS applications in drug development. Mass Spectrom. Rev., 1999, 18(3), 187-279.
35. Wu, Y. The use of liquid chromatography-mass spectrometry for the identification of drug degradation products in pharmaceutical formulations. Biomed. Chromatogr., 2000, 14(6), 384-396.
36. Lindegardh, N.; Giorgi, F.; Galletti, B.; Mattia, M.D.; Quaglia, M.; Carnevale, D.; White, N.J.; Mazzanti, A.; Day, N.P.J.; Identification of an isomer impurity in piperaquine drug substance. J. Chromatogr., 2006, 1135, 166-169.
37. Liu, D.Q.; Chen, T.K.; McGuire, M.A.; Kord, A.S. Analytical control of genotoxic impurities in the pazopanib hydrochloride manufacturing process. J. Pharm. Biomed. Anal., 2009, 50, 144-150.
38. Novak, P.; Tepe, P.; Fistri, I.; Brato, I.; Gabelica, V. The application of LC-NMR and LC-MS for the separation and rapid structure elucidation of an unknown impurity in 5-aminosalicylic acid. J. Pharm. Biomed. Anal., 2006, 40, 1268-1272.
39. Vijayan, M.; Deecaraman, M.; Pudupalayam, K.T. In vitro geno-toxicity of piperacillin impurity-A. African J. Biotech., 2007, 6, 2074-2077.
40. Joseph, T.; Raj, S.; Bharathi, C.; Kumar, S.; Joseph, P.; Kumar, N.; Sharma, H.; Parikh K. Identification, isolation and characterization of process-related impurities in Rizatriptan benzoate. J. Pharm. Biomed. Anal., 2009, 49, 156-162.
41. Bharathi, C.; Prasad, S.; Bharathi, D.V.; Shankar, R.; Rao, V.J.; Dandala, R.; Naidu, A. Structural identification and characterization of impurities in ceftizoxime sodium. J. Pharm. Biomed. Anal., 2007, 43, 733-740.
42. Prasada Rao, K.V.V.; Rani, A.; Reddy, A.V.R.; Bharathi, C.H.; Dandala, R.; Naidu, A. Isolation, structural elucidation and characterization of impurities in Cefdinir. J. Pharm. Biomed. Anal., 2007, 43, 1476-1482.
43. Reddy, G.M.; Bhaskar, B.V.; Reddy, P.P.; Ashok, S.; Sudhakar, P.; Moses B. J.; Vyas, K.; Mukkanti, K. Structural identification and characterization of potential impurities of pantoprazole sodium. J. Pharm. Biomed. Anal., 2007, 45, 201-210.
44. An, J.; Sun, M.; Bai, L.; Chen, T.; Liu, D.Q.; Kord, A. A practical derivatization LC/MS approach for determination of trace level al-kyl sulfonates and dialkyl sulfates genotoxic impurities in drug substances. J. Pharm. Biomed. Anal., 2008, 48, 1006-1010.
45. Vuletic, M.; Cindric, M.; Dogan, J.; Znjak, K. Identification of unknown impurities in simvastatin substance and tablets by liquid chromatography/tandem mass spectrometry. J. Pharm. Biomed. Anal., 2005, 37, 715-721.
46. Dongre, V.G.; Karmuse, P.P.; Ghugre, P.D.; Salunke, S.M.; Panda, N.; Kumar, A. Preparative isolation and structural elucidation of impurities in fluconazole by LC/MS/MS. J. Pharm. Biomed. Anal., 2006, 42, 334-340.
47. Babu, J.M.; Nageshwar, D.; Kumar, Y.R.; Prabhakar, C.; Sarma, M.R.; Reddy G.O.; Vyas, K. Structural studies on the impurities of troglitazone. J. Pharm. Biomed. Anal., 2003, 31, 271-281.
48. Raman, B.; Sharma, B.A.; Butala, R.; Ghugare, P.D.; Kumar, A. Structural elucidation of a process-related impurity in ezetimibe by LC/MS/MS and NMR. J. Pharm. Biomed. Anal., 2010, 52, 73-78.
49. Rourick, R.A.; Volk, K.J.; Klohr, S.E.; Spears, T.; Kerns, E.H.; Lee M.S. Predictive strategy for the rapid structure elucidation of drug degradants. J. Pharm. Biomed. Anal., 1996, 14, 1743-1752.
50. Beasley, C.A.; Hwang, T.; Fliszar, K.; Abend, A.; McCollum, D.G.; Reed, R.A. Identification of impurities in ivermectin bulk material by mass spectrometry and NMR. J. Pharm. Biomed. Anal., 2006, 41, 1124-1134.
51. Qiua, F.; Penninoa S.; Busaccab C. A.; Norwooda D. L. Identification of a process impurity formed during synthesis of a nevirapine analogue HIV NNRT inhibitor using LC/MS and forced degradation. J. Pharm. Biomed. Anal., 2009, 49, 733-738
52. Chaudhari, A.; Maikap G.; Deo A.; Vivek K.; Agrawal H.; Pe-shawe U.; Gawande A.; Sompalli S.; Mane S.; Jadhav D.; Chaud-hari A. Isolation and structural elucidation of two impurities from a diacerein bulk drug. J. Pharm. Biomed. Anal., 2009, 49, 525-528.
53. Bharathi, C.; Jayaram, P.; Raj, J.S.; Kumar, M.S.; Bhargavi, V.; Handa, V.K.; Dandala, R.; Naidu, A. Identification, isolation and characterization of impurities of clindamycin palmitate hydrochlorid. J. Pharm. Biomed. Anal., 2008, 48, 1211-1218.
54. Dongre, V.G.; Karmuse, P.P.; Ghugare, P.D.; Gupta, M.; Nerurkar, B.; Shaha, C.; Kumar, A. Characterization and quantitative determination of impurities in piperaquine phosphate by HPLC and LC/MS/MS. J. Pharm. Biomed. Anal., 2007, 43, 186-195.
55. Kocijana, A.; Graheka, R.; Zupancic-Kralj, L. Identification of an impurity in pravastatin by application of collision-activated decomposition mass spectra. Acta. Chim. Slov., 2006, 53, 464-468.
56. Ferrer, I.E.; Thurman, M. Liquid chromatography/ time-of-flight/mass spectrometry (LC/TOF/MS) for the analysis of emerging contaminants. Trends Anal. Chem., 2003, 22(10), 750-756.
57. Novak, T.J.; Grinberg, N.; Hartman, B.; Marcinko, S.; DiMichele, L.; Mao, B. LCMS using a hybrid quadrupole time of flight mass spectrometer for impurity identification during process chemical development of a novel integrase inhibitor. J. Pharm. Biomed. Anal., 2010, 51, 78-83.
58. Plumb, R.S.; Jones, M.D.; Rainville, P.D.; Nicholson, J.K. A rapid simple approach to screening pharmaceutical products using ultra-performance LC coupled to time of- flight mass spectrometry and pattern recognition. J. Chromatogr. Sci., 2008, 46, 193-198.
59. Zhou, H.; Zheng, Z.; Wu, S.; Tai, Y.; Cao, X.; Pan, Y. Separation and characterization of clindamycin and related impurities in bulk drug by high-performance liquid chromatography-electrospray tandem mass spectrometry. J. Pharm. Biomed. Anal., 2006, 41, 1116-1123.
60. Sun, C.; Wu, J.; Wang, D.; Pan, Y. Characterization of a novel impurity in bulk drug eprosartan by ESI/MSn and NMR. J. Pharm. Biomed. Anal., 2010, 51, 778-783.
61. Zhanga, H.; Yang, X. Profiling and quantification of isoflavone-C-glycosides impurities in puerarin injection by liquid chromatography coupled to ESI-ion trap mass spectrometry. J. Pharm. Biomed. Anal., 2009, 49, 843-847.
62. Denk, O.M.; Skellern, G.G.; Watson D.G. Impurity profiling of pholcodine by liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS). J. Pharm. Pharmacol., 2002, 54(1), 87-98.
63. Ramana, B.; Sharma B. A.; Ghugareb P. D.; Pravin P.; Karmuse, A. K. Semi-preparative isolation and structural elucidation of an impurity in citalopram by LC/MS/MS. J. Pharm. Biomed. Anal., 2009, 50, 377-383.