Analytical power of LLE-HPLC-PDA-MS/MS in drug metabolism studies: Identification of new nabumetone metabolites

Journal of Pharmaceutical and Biomedical Analysis

Volumn 80, Issue , 2013, Pages 164-172

  Nobilis, Milan ^a,b   Mikušek, Jiří ^b   Szotáková, Barbora ^b   Jirásko, Robert ^c   Holčapek, Michal ^c   Chamseddin, Chamseddin ^d   Jira, Thomas ^d   Kučera, Radim ^b   Kuneš, Jiří ^b   Pour, Milan ^b  

^a INSTITUTE OF MATHEMATICS   (Czech Republic)

^b Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^c UNIVERSITY OF PARDUBICE   (Czech Republic)

^d UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

3 Hydroxy nabumetone; Chiral and achiral LLE HPLC PDA ESI MS MS identification of metabolites; Intermediate between nabumetone and 6 methoxy 2 naphthylacetic acid (6 MNA); Metabolites of 3 hydroxy nabumetone; Rat and human microsomal fraction; Rat isolated hepatocytes

Indexed keywords

4 (6 METHOXY 2 NAPHTHYL) 3 HYDROXYBUTAN 2 ONE (3HYDROXY NABUMETONE); CARBONYL DERIVATIVE; DRUG METABOLITE; GLUCURONIC ACID; HYDROXYL GROUP; NABUMETONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMICAL COMPOSITION; CHIRALITY; DEMETHYLATION; DRUG ABSORPTION; DRUG CONJUGATION; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG RETENTION; DRUG STRUCTURE; DRUG TRANSFORMATION; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROXYLATION; IN VITRO STUDY; LIQUID LIQUID EXTRACTION; MASS SPECTROMETRY; MICROSOME; NONHUMAN; POLARIMETRY; PRIORITY JOURNAL; RAT; REDUCTION; SYNTHESIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BUTANONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HEPATOCYTES; HUMANS; MALE; MICROSOMES, LIVER; NAPHTHALENEACETIC ACIDS; PRODRUGS; RATS; RATS, WISTAR; SPECTRUM ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 84876305684     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.03.006     Document Type: Article

References (23)

1. Hedner T., Samulesson O., Währborg P., Wadenvik H., Ung K.-A., Ekbom A. Nabumetone - therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. Drugs 2004, 64:2315-2343.
2. Haddock R.E., Jeffery D.J., Lloyd J.A., Thawley A.R. Metabolism of nabumetone (BRL-14777) by various species including man. Xenobiotica 1984, 14:327-337.
3. Nobilis M., Kopecký J., Květina J., Svoboda Z., Pour M., Kuneš J., Holčapek M., Kolářová L. Comparative biotransformation and disposition studies of nabumetone in humans and minipigs using high-performance liquid chromatography with ultraviolet, fluorescence and mass spectrometric detection. J. Pharm. Biomed. Anal. 2003, 32:641-656.
4. Nobilis M., Holčapek M., Kolářová L., Kopecký J., Kuneš M., Svoboda Z., Květina J. Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection. J. Chromatogr. A 2004, 1031:229-236.
5. Altun Y., Dogan B., Ozkan S.A., Uslu B. Development and validation of voltammetric techniques for nabumetone in pharmaceutical dosage form, human serum and urine. Acta Chim. Slov. 2007, 54:287-294.
6. Pulgarin J.A.M., Molina A.A., Robles I.S.F. Simple and rapid determination of the active metabolite of nabumetone in biological fluids by heavy atom-induced room temperature phosphorescence. Anal. Chim. Acta 2005, 554:37-42.
7. Rote A.R., Bhalerao S.R. Development and statistical validation of spectrophotometric methods for the estimation of nabumetone in tablet dosage form. E-J. Chem. 2010, 7:1463-1467.
8. Starek M., Laskawski S., Dabrowska M. Identification and quantitative determination of nabumetone in pharmaceutical preparations by TLC-densitometry. JPC-J. Planar Chromatogr.-Mod. TLC 2011, 24:513-519.
9. Gandhi S.V., Ranher S.S., Deshpande P.B., Shah D.K. Simultaneous HPTLC determination of nabumetone and paracetamol in combined tablet dosage form. J. Braz. Chem. Soc. 2011, 22:1068-1072.
10. Sahu P.K., Annapurna M.M. Analysis of nabumetone in bulk and tablet formulation by a new and validated reverse phase high performance liquid chromatography. E-J. Chem. 2009, 6:S59-S64.
11. Patel B.N., Sharma N., Sanyal M., Prasad A., Shrivastav P.S. High-throughput LC-MS/MS assay for 6-methoxy-2-naphthylacetic acid, an active metabolite of nabumetone in human plasma and its application to bioequivalence study. Biomed. Chromatogr. 2008, 22:1213-1224.
12. Zerzaňová A., Císař P., Klimeš J. Comparison of different stationary phases for bioanalytical studies of biologically active compounds. J. Sep. Sci. 2006, 29:2126-2135.
13. Sheen J.F., Her G.R. Application of pentafluorophenyl hydrazine derivatives to the analysis of nabumetone and testosterone in human plasma by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spektrometry. Anal. Bioanal. Chem. 2004, 380:891-897.
14. Turpeinen M., Hofmann U., Klein K., Muerdter T., Schwab M., Zanger U.M. A predominate role of CYP1A2 for the metabolism of nabumetone to the active metabolite, 6-methoxy-2-naphthylacetic acid, in human liver microsomes. Drug Metab. Dispos. 2009, 37:1017-1024.
15. Matsumoto K., Nemoto E., Hasegawa T., Akimoto M., Sugibayashi K. In vitro characterization of the cytochrome P450 isoforms involved in the metabolism of 6-methoxy-2-napthylacetic acid, an active metabolite of the prodrug nabumetone. Biol. Pharm. Bull. 2011, 34:734-739.
16. Smith P.K., Krohn R.I., Hermanson G.T., Mallia A.K., Gartner F.H., Provenzano M.D., Fujimoto E.K., Goeke N.M., Olson B.J., Klenk D.C. Measurement of protein using bicinchoninic acid. Anal. Biochem. 1985, 150:76-85.
17. Berry M.N., Edwards A.M., Barritt G.J. Isolated hepatocytes preparation, properties and applications. Laboratory Techniques in Biochemistry and Molecular Biology 1991, 15-35. Elsevier Science, Amsterdam. R.H. Burdow, P.H. van Knippenberg (Eds.).
18. Nobilis M., Jira T., Lísa M., Holčapek M., Szotáková B., Lamka J., Skálová L. Achiral and chiral high-performance liquid chromatographic determination of flubendazole and its metabolites in biomatrices using UV photodiode-array and mass spectrometric detection. J. Chromatogr. A 2007, 1149:112-120.
19. Nobilis M., Vybíralová Z., Křížová V., Kubíček V., Soukupová M., Lamka J., Szotáková B., Skálová L. Sensitive chiral high-performance liquid chromatographic determination of anthelmintic flubendazole and its phase I metabolites in blood plasma using UV photodiode-array and fluorescence detection application to pharmacokinetic studies in sheep. J. Chromatogr. B 2008, 876:89-96.
20. Kučera R., Nobilis M., Skálová L., Szotáková B., Císař P., Jira T., Klimeš J., Wsól V. Use of chiral liquid chromatography for the evaluation of stereospecificity in the carbonyl reduction of potential benzo[c]fluorene antineoplastics benfluron and dimefluron in various species. J. Pharm. Biomed. Anal. 2005, 37:1049-1057.
21. Bertucci C., Pistolozzi M., Simone A.D. Circular dichroism in drug discovery and development: an abridged review. Anal. Bioanal. Chem. 2010, 398:155-166.
22. Harada N., Nakanishi K. Circular Dichroic Spectroscopy Exciton Coupling in Organic Stereochemistry 1983, University Science Books, Mill Valley, CA.
23. A.C. Goudie, Naphthalene derivatives, a process for their preparation and their use in anti-inflammatory pharmaceutical compositions, United States Patent 4382959 (10 May 1983).