Collision-induced dissociation of valdecoxib metabolites: A novel rearrangement involving an isoxazole ring

Journal of Mass Spectrometry

Volumn 39, Issue 3, 2004, Pages 295-302

  Zhang, Ji Y ^a,b   Xu, Fran ^a   Breau, Alan P ^a  

^a PFIZER INC   (United States)

^b GLAXOSMITHKLINE   (United States)

Author keywords

Collision induced dissociation; COX 2 inhibitor; Isoxaxole; Liquid chromatography tandem mass spectrometry; Rearrangement; Valdecoxib

Indexed keywords

CHEMICAL BONDS; INORGANIC ACIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; NEGATIVE IONS;

MASS SPECTRAL REARRANGEMENT;

METABOLITES;

ANION; CARBOXYLIC ACID DERIVATIVE; DRUG METABOLITE; ISOXAZOLE DERIVATIVE; NITROGEN; OXYGEN; STABLE ISOTOPE; VALDECOXIB;

ACCURACY; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; CROSS LINKING; DRUG DEGRADATION; DRUG DETERMINATION; DRUG METABOLISM; DRUG STRUCTURE; ISOTOPE LABELING; PRIORITY JOURNAL; QUADRUPOLE MASS SPECTROMETRY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; TIME OF FLIGHT MASS SPECTROMETRY;

ANIMALS; CHROMATOGRAPHY, LIQUID; CYCLOOXYGENASE INHIBITORS; HUMANS; ISOXAZOLES; MASS SPECTROMETRY; SULFONAMIDES;

EID: 1642350892     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.582     Document Type: Article

References (16)

1. Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, Perkins WE, Rogers RS, Shaffer AF, Zhang YY, Zweifel BS, Seibert K. 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, Valdecoxib: A potent and selective inhibitor of COX-2. J. Med. Chem. 2000; 43: 775.
2. Camu F, Beecher T, Recker DP, Verburg KM. Valdecoxib, a COX-2-specific inhibitor, is an efficacious, opioid-sparing analgesic in patients undergoing hip arthroplasty. Am. J. Ther. 2002; 9: 43.
3. Fricke J, Varkalis J, Zwillich S, Adler R, Forester E, Recker DP, Verburg KM. Valdecoxib is more efficacious than rofecoxib in relieving pain associated with oral surgery. Am. J. Ther. 2002; 9: 89.
4. Fu JY, Masferrer JL, Seibert K, Raz A, Needleman P. The induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes. J. Biol. Chem. 1990; 265: 16737.
5. Vane JR, Bakhle YS, Botting RM. Cyclooxygense 1 and 2. Annu. Rev. Pharmacol. Toxicol. 1998; 38: 97.
6. Donnelly MT, Hawkey CJ. COX-2 inhibitors-a new generation of safer NSAIDs? Aliment. Pharmacol. Ther. 1997; 11: 227.
7. Pennisi E. Building better aspirin and Does aspirin ward off cancer and Alzheimer's. Science 1998; 280: 1191.
8. Simon LS, Lanza FL, Lipsky PE, Hubbard RC, Talwalker S, Schwartz BD, Isakson PC, Geis GS. Preliminary study of the safety and efficacy of SC-58635, a novel cycolooxygenase 2 inhibitor. Arthritis Rheum. 1998; 41: 1591.
9. Isakson PC, Zweifel BS, Masferrer JL, Koboldt C, Seibert K, Hubbard RC, Geis GS, Needleman P. Specific COX-2 inhibitors: From bench to bedside, In Selective COX-2 Inhibitors: Pharmacology, Clinical Effects and Therapeutic Potential, Vane J and Botting J (eds). Kluwer: Dordrecht and William Harvey Press: London, 1998; pp. 127-133.
10. Yuan JJ, Yang D, Zhang JY, Bible R, Karim A, Findlay JAW. Disposition of a specific Cox-2 inhibitor, Valdecoxib, in human. Drug Metab. Dispos. 2002; 30: 1013.
11. Zhang JY, Yuan JJ, Wang YF, Bible R, Breau AP. Pharmacokinetics and metabolism of a COX-2 inhibitor, Valdecoxib, in mice. Drug Metab. Dispos. 2003; 31: 491.
12. Paulson SK, Zhang JY, Breau AP, Hribar JD, Liu NW, Jessen SM, Lawal YM, Cogburn JN, Gresk CJ, Markos CS, Maziasz TJ, Schoenhard GL, Burton EG. Pharmacokinetics, tissue distribution, metabolism, and excretion of celecoxib in rats. Drug Metab. Dispos. 2000; 28: 514.
13. Paulson SK, Zhang JY, Jessen SM, Lawal Y, Liu NW, Dudkowski CM, Wang YF, Chang M, Yang D, Findlay JW, Berge MA, Markos CS, Breau AP, Hribar JD, Yuan J. Comparison of celecoxib metabolism and excretion in mouse, rabbit, dog, cynomolgus monkey and rhesus monkey. Xenobiotica 2000; 30: 731.
14. Zhang JY, Wang YF, Dudkowski C, Yang D, Chang M, Yuan J, Paulson SK, Breau AP. Characterization of metabolites of celecoxib in rabbits by liquid chromatography/tandem mass spectrometry. J. Mass Spectrom. 2000; 35: 1259.
15. Zhang JY, Fast DF, Breau AP. Development and validation of a liquid chromatography-tandem mass spectrometric assay for eplerenone and its hydrolyzed metabolite in human plasma. J. Chromatogr. B 2003; 787: 333.
16. Zhang JY, Fast DF, Breau AP. Development and validation of an automated SPE-LC-MS/MS assay for valdecoxib and its hydroxylated metabolite in human plasma. J. Pharm. Biomed. Anal. 2003; 33: 61.