Characterization of forced degradation products of ketorolac tromethamine using LC/ESI/Q/TOF/MS/MS and in silico toxicity prediction

Journal of Mass Spectrometry

Volumn 49, Issue 5, 2014, Pages 380-391

  Kalariya, Pradipbhai D ^a   Raju, B ^b   Borkar, Roshan M ^b   Namdev, Deepak ^a   Gananadhamu, S ^a   Nandekar, Prajwal P ^c   Sangamwar, Abhay T ^c   Srinivas, R ^a,b  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^c NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

accurate mass measurements; anti inflammatory; degradation products; forced degradation; in silico toxicity; ketorolac tromethamine; LC ESI MS MS

Indexed keywords

ELECTROSPRAY IONIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; TOXICITY;

ACCURATE MASS MEASUREMENTS; ANTI-INFLAMMATORIES; DEGRADATION PRODUCTS; FORCED DEGRADATION; IN-SILICO; KETOROLAC TROMETHAMINE; LC/ESI/MS/MS;

DEGRADATION;

ACETONITRILE; AMMONIUM FORMATE; KETOROLAC TROMETAMOL;

ARTICLE; COMPUTER MODEL; DRUG DEGRADATION; DRUG HYDROLYSIS; ELECTROSPRAY IONIZATION QUADRUPOLE TIME OF FLIGHT TANDEM MASS SPECTROMETRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOTOLYSIS; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; ANIMAL; CHEMISTRY; COMPUTER SIMULATION; FEMALE; LIQUID CHROMATOGRAPHY; MALE; MOUSE; OXIDATION REDUCTION REACTION; PROCEDURES; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY; TOXICITY TESTING;

ANIMALS; CHROMATOGRAPHY, LIQUID; COMPUTER SIMULATION; FEMALE; KETOROLAC TROMETHAMINE; MALE; MICE; OXIDATION-REDUCTION; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; TANDEM MASS SPECTROMETRY; TOXICITY TESTS;

EID: 84900004860     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3351     Document Type: Article

References (38)

1. K. M. Litvak, G. K. McEvoy, Ketorolac, an injectable nonnarcotic analgesic, Clin. Pharm. 1990, 9, 921.
2. R. W. Yee,. Analgesic efficacy and safety of nonpreserved ketorolac tromethamine ophthalmic solution following radial keratotomy. Am. J. Optha. 1998, 125, 472.
3. D. J. Reinhart,. Minimising the adverse effects of ketorolac. Drug safe. 2000, 22, 487.
4. FDA. Guideline for Submitting Documentation for the Stability of Human Drugs and Biologics. Food and Drug Administration: Rockville, MD, 1987.
5. ICH guideline, Q1A (R2) Stability Testing of New Drug Substances and Products, International Conference on Harmonisation, IFPMA, Geneva, Switzerland., 2000.
6. S. Singh, T. Handa, M. Narayanam, A. Sahu, M. Junwal, R. P. Shah,. A critical review on the use of modern sophisticated hyphenated tools in the characterization of impurities and degradation products. J. Pharm. Biomed. Anal. 2012, 69, 148.
7. B. Raju, M. Ramesh, R. Srinivas, R. S. Satyanarayana, Y. Venkateswarlu,. Identification and characterization of stressed degradation products of prulifloxacin using LC-ESI-MS/Q-TOF, MSn experiments: development of a validated specific stability-indicating LC-MS method. J. Pharm. Biomed. Anal. 2011, 56, 560.
8. R. M. Borkar, B. Raju, R. Srinivas, P. Patel, S. K. Shetty,. Identification and characterization of stressed degradation products of metoprolol using LC/Q-TOF-ESI-MS/MS and MSn experiments. Biomed. Chromatogr. 2012, 26, 720.
9. R. M. Borkar, B. Raju, P. S. Devrukhakar, T. Naresh, A. B. N. Nageswara Rao, R. Srinivas,. Liquid chromatography/electrospray ionization tandem mass spectrometric study of milnacipran and its stressed degradation products. Rapid Commun. Mass Spectrom. 2013, 27, 369.
10. C. Purna chander, B. Raju, A. Sulthana, R. Srinivas,. Liquid chromatography electrospray ionization tandem mass spectrometric (LC-ESI-MS/MS) study of carvedilol and its stress degradation products. Anal. Meth 2013, 5, 4330.
11. D. J. Jones, A. R. Bjorksten,. Detection of ketorolac enantiomers in human plasma using enantioselective liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl. 1994, 661, 165.
12. F. J. Flores-Murrieta, V. Granados-Soto, E. Hong,. Determination of ketorolac in blood and plasma samples by high-performance liquid chromatography. Boll. Chim. Farm. 1994, 133, 588.
13. Z. Wang, R. M. Dsida, M. J. Avram,. Determination of ketorolac in human plasma by reversed-phase high-performance liquid chromatography using solid-phase extraction and ultraviolet detection. J. Chromatogr. B Biomed. Sci. Appl. 2001, 755, 383.
14. S. Demircan, F. Sayin, N. E. Basci, N. Unlu, S. Kir,. Determination of ketorolac tromethamine in human eye samples by HPLC with photo diode-array detection. Chromatographia 2007, 66, 135.
15. B. Raju, M. Ramesh, R. M. Borkar, R. Padiya, S. K. Banerjee, R. Srinivas,. Development and validation of liquid chromatography-mass spectrometric method for simultaneous determination of moxifloxacin and ketorolac in rat plasma: application to pharmacokinetic study. Biomed. Chromatogr. 2012, 26, 1341.
16. I. Tsina, F. Chu, M. Kaloostian, M. Pettibone, A. Wu,. HPLC method for the determination of ketorolac in human plasma. J. Liq. Chromatogr. Relat Technol. 1996, 19, 957.
17. I. Tsina, Y. L. Tam, A. Boyd, C. Rocha, I. Massey, T. Tarnowski,. An indirect (derivatization) and a direct HPLC method for the determination of the enantiomers of ketorolac in plasma. J. Pharm. Biomed. Anal. 1996, 15, 403.
18. R. S. Chaudhary, S. S. Gangwal, K. C. Jindal, S. Khanna,. Reversed-phase high-performance liquid chromatography of ketorolac and its application to bioequivalence studies in human serum. J. Chromatogr. B Biomed. Sci. Appl. 1993, 614, 180.
19. L. Franceschi, M. Furlanut,. A simple and sensitive HPLC method to monitor serum and synovial fluid concentrations of ketorolac in reumathologic patients. J. Bioanal Biomed. 2010, 2, 121.
20. P. J. Hayball, J. G. Tamblyn, Y. Holden, J. Wrobel,. Stereoselective analysis of ketorolac in human plasma by high-performance liquid chromatography. Chirality 1993, 5, 31.
21. K. R. Lorenzini, J. A. Desmeules, M. Besson, J.-L. Veuthey, P. Dayer, Y. Daali,. Two-dimensional liquid chromatography-ion trap mass spectrometry for the simultaneous determination of ketorolac enantiomers and paracetamol in human plasma: application to a pharmacokinetic study. J. Chromatogr. A 2009, 1216, 3851.
22. M. A. Radwana, B. T. AlQuadeibb, N. M. Aloudaha, H. Y. Aboul Enein,. Pharmacokinetics of ketorolac loaded to polyethylcyanoacrylate nanoparticles using UPLC MS/MS for its determination in rats. Int. J. Pharm. 2010, 397, 173.
23. B. Raju, M. Ramesh, R. M. Borkar, R. Padiya, S. K. Banerjee, R. Srinivas,. Identification and structural characterization of in vivo metabolites of ketorolac using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS). J. Mass Spectrom. 2012, 47, 919.
24. B. V. Kamath, K. Shivram, S. Vangani,. Spectrophotometric determination of ketorolac tromethamine by charge transfer and ion-pair complexation. Anal. lett. 1994, 27, 103.
25. P. V. Devarajan, S. P. Gore, S. V. Chavan,. HPTLC determination of ketorolac tromethamine. J. Pharm. Biomed. Anal. 2000, 22, 679.
26. S. Orlandini, S. Furlanetto, S. Pinzauti, G. D'Orazio, S. Fanali,. Analysis of ketorolac and its related impurities by capillary electrochromatography. J. Chromatogr. A 2004, 1044, 295.
27. J. C. Sturm, H. Canelo, L. J. Nunez-Vergara, J. A. Squella,. Voltammetric study of ketorolac and its differential pulse polarographic determination in pharmaceuticals. Talanta 1997, 44, 931.
28. Z. Guorong, L. Wenhua, C. Shaofeng, S. Tianlin,. Determination of ketorolac tromethamine by derivative adsorptive chronopotentiometry. Chin. J. Anal. Chem. 1998, 10, 022.
29. S. N. Razzaq, I. Mariam, I. U. Khan, M. Ashfaq,. Development and validation of liquid chromatographic method for gatifloxacin and ketorolac tromethamine in combined dosage form. J. Liq. Chromatogr. Relat Technol. 2012, 35, 651.
30. S. N. Razzaq, I. U. Khan, M. Ashfaq, I. Mariam,. Stability indicating HPLC method for simultaneous determination of moxifloxacin hydrochloride and ketorolac tromethamine in pharmaceutical formulations. Quim. Nova. 2012, 35, 1216.
31. K. Gandla, J. M. R. Kumar, D. Bikshapathi, R. Spandana,. A validated RP-HPLC method for simultaneous estimation of febuxostat and ketorolac tromethamine in pharmaceutical formulations. J. Drug Deliv Ther. 2012, 2, 173.
32. M. Salaris, M. Nieddu, N. Rubattu, C. Testa, E. Luongo, M. G. Rimoli, G. Boatto,. Acid and base degraded products of ketorolac. J. Pharm. Biomed. Anal. 2010, 52, 320.
33. British Pharmacopoeia, Vol. II, 2009, pp. 1175.
34. ICH Q2(R1) International Conference on Harmonization (ICH) of Technical Requirements for Registration of Pharmaceuticals for Human Use, Topic Q2 (R1): Validation of Analytical Procedures: Text and Methodology, November 2005.
35. H. H. Tonnesen, The Photostability of Drugs and Drug Formulations. Taylor & Francis Ltd: London, 2003, 34.
36. N. F. Cariello, J. D. Wilson, B. H. Britt, D. J. Wedd, B. Burlinson, V. Gombar,. Comparison of the computer programs derek and topkat to predict bacterial mutagenicity. Mutagenesis 2002, 17, 321.
37. L. Muller, R. J. Mauthe, C. M. Riley, M. M. Andino, D. D. Antonis, C. Beels, J. DeGeorge, A. G. M. De Knaep, D. Ellison, J. A. Fagerland,. A rationale for determining, testing, and controlling specific impurities in pharmaceuticals that possess potential for genotoxicity. Regul. Toxicol. Pharmacol. 2006, 44, 198.
38. G. F. Gerberick, C. A. Ryan, P. S. Kern, H. Schlatter, R. J. Dearman, I. Kimber, G. Y. Patlewicz, D. A. Basketter,. Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods. Dermatitis. 2005, 16, 157.