Stereoselective method to quantify bupropion and its three major metabolites, hydroxybupropion, erythro-dihydrobupropion, and threo-dihydrobupropion using HPLC-MS/MS

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 1015-1016, Issue , 2016, Pages 201-208

  Masters, Andrea R ^a   McCoy, Michael ^b   Jones, David R ^c   Desta, Zeruesenay ^c  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Phenomenex   (United States)

^c Laboratory Medicine   (United States)

Author keywords

4 Hydroxybupropion; Bupropion; Enantiomers; Erythro Dihydrobupropion; HPLC MS MS; Stereoselective; Threo Dihydrobupropion

Indexed keywords

AMMONIUM BICARBONATE; AMMONIUM HYDROXIDE; BIOMOLECULES; DRUG INTERACTIONS; ELECTROSPRAY IONIZATION; ENANTIOMERS; EXTRACTION; LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETRY; METABOLITES; STEREOSELECTIVITY;

4-HYDROXYBUPROPION; BUPROPION; ERYTHRO; HPLC-MS/MS; STEREO-SELECTIVE; THREO-DIHYDROBUPROPION;

DRUG PRODUCTS;

ACETONITRILE; AMFEBUTAMONE; AMMONIA; AMMONIUM HYDROXIDE; BICARBONATE; DRUG METABOLITE; ERYTHRO DIHYDROBUPROPION; METHANOL; PARACETAMOL; RADAFAXINE; THREO DIHYDROBUPROPION; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CONTROLLED STUDY; DRUG DISPOSITION; DRUG METABOLISM; DRUG STABILITY; ELECTROSPRAY; ELIMINATION HALF-LIFE; ENANTIOMER; ENVIRONMENTAL TEMPERATURE; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIQUID LIQUID EXTRACTION; MALE; NORMAL HUMAN; PHARMACOKINETIC PARAMETERS; PLASMA; PRIORITY JOURNAL; SINGLE DRUG DOSE; STEREOCHEMISTRY; TANDEM MASS SPECTROMETRY; ADOLESCENT; ANALOGS AND DERIVATIVES; BLOOD; CHEMISTRY; LIMIT OF DETECTION; MIDDLE AGED; PROCEDURES; REPRODUCIBILITY; STEREOISOMERISM; YOUNG ADULT;

ADOLESCENT; ADULT; BUPROPION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; FEMALE; HUMANS; LIMIT OF DETECTION; MALE; MIDDLE AGED; REPRODUCIBILITY OF RESULTS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; YOUNG ADULT;

EID: 84959195530     PISSN: 15700232     EISSN: 1873376X     Source Type: Journal    
DOI: 10.1016/j.jchromb.2016.02.018     Document Type: Article

References (33)

1. Stahl S.M., Pradko J.F., Haight B.R., Modell J.G., Rockett C.B., Learned-Coughlin S. A review of the neuropharmacology of bupropion, a dual norepinephrine and dopamine reuptake inhibitor. Prim. Care Companion J. Clin. Psychiatry 2004, 6(4):159-166.
2. Dhillon Sohita, Yang Lily P.H., Curran Monique P. Bupropion: a review of its use in the management of major depressive disorder. Drugs 2008, 68(5):653-689.
3. Dwoskin Linda P., Rauhut Anthony S., King-Pospisil Kelley A., Bardo Michael T. Review of the pharmacology and clinical profile of bupropion, an antidepressant and tobacco use cessation agent. CNS Drug Rev. 2006, 12(3-4):178-207.
4. Bondarev M.L., Bondareva T.S., Young R., Glennon R.A. Behavioral and biochemical investigations of bupropion metabolites. Eur. J. Pharmacol. 2003, 474(August (1)):85-93.
5. Perumal A.S., Smith T.M., Suckow R.F., Cooper T.B. Effect of plasma from patients containing bupropion and its metabolites on the uptake of norepinephrine. Neuropharmacology 1986, 25(February (2)):199-202.
6. Golden R.N., De Vane C.L., Laizure S.C., Rudorfer M.V., Sherer M.A., Potter W.Z. Bupropion in depression: II. The role of metabolites in clinical outcome. Arch. Gen. Psychiatry 1988, 45(February (2)):145-149.
7. Martin P., Massol J., Colin J.N., Lacomblez L., Puech A.J. Antidepressant profile of bupropion and three metabolites in mice. Pharmacopsychiatry 1990, 23(July (4)):187-194.
8. Damaj M.I., Carroll F.I., Eaton J.B., Navarro H.A., Blough B.E., Mirza S., Lukas R.J., Martin B.R. Enantioselective effects of hydroxy metabolites of bupropion on behavior and on function of monoamine transporters and nicotinic receptors. Mol. Pharmacol. 2004, 66(September (3)):675-682.
9. Ascher J.A., Cole J.O., Colin J.N., Feighner J.P., Ferris R.M., Fibiger H.C., Golden R.N., Martin P., Potter W.Z., Richelson E., et al. Bupropion: a review of its mechanism of antidepressant activity. J. Clin. Psychiatry 1995, 56(September (9)):395-401.
10. Hansard M.J., Jackson M.J., Smith L.A., Rose S., Jenner P. A major metabolite of bupropion reverses motor deficits in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated common marmosets. Behav. Pharmacol. 2011, 22(June (3)):269-274.
11. Zhu A.Z., Cox L.S., Nollen N., Faseru B., Okuyemi K.S., Ahluwalia J.S., Benowitz N.L., Tyndale R.F. CYP2B6 and bupropion's smoking-cessation pharmacology: the role of hydroxybupropion. Clin. Pharmacol. Ther. 2012, 92(December (6)):771-777.
12. Suckow R.F., Zhang M.F., Cooper T.B. Enantiomeric determination of the phenylmorpholinol metabolite of bupropion in human plasma using coupled achiral-chiral liquid chromatography. Biomed. Chromatogr. 1997, 11(May-June (3)):174-179.
13. Xu H., Loboz K.K., Gross A.S., McLachlan A.J. Stereoselective analysis of hydroxybupropion and application to drug interaction studies. Chirality 2007, 19(March (3)):163-170.
14. Coles R., Kharasch E.D. Stereoselective analysis of bupropion and hydroxybupropion in human plasma and urine by LC/MS/MS. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2007, 857(September (1)):67-75.
15. Benowitz N.L., Zhu A.Z., Tyndale R.F., Dempsey D., Jacob P. Influence of CYP2B6 genetic variants on plasma and urine concentrations of bupropion and metabolites at steady state. Pharmacogenet. Genomics 2013, 23(March (3)):135-141.
16. Meyer A., Vuorinen A., Zielinska A.E., Strajhar P., Lavery G.G., Schuster D., Odermatt A. Formation of threohydrobupropion from bupropion is dependent on 11β-hydroxysteroid dehydrogenase 1. Drug Metab. Dispos. 2013, 41(September (9)):1671-1678.
17. Faucette S.R., Hawke R.L., Lecluyse E.L., Shord S.S., Yan B., Laethem R.M., Lindley C.M. Validation of bupropion hydroxylation as a selective marker of human cytochrome P450 2B6 catalytic activity. Drug Metab. Dispos. 2000, 28(October (10)):1222-1230.
18. Hesse L.M., Venkatakrishnan K., Court M.H., von Moltke L.L., Duan S.X., Shader R.I., Greenblatt D.J. CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants. Drug Metab. Dispos. 2000, 28:1176-1183.
19. Skarydova L., Tomanova R., Havlikova L., Stambergova H., Solich P., Wsol V. Deeper insight into the reducing biotransformation of bupropion in the human liver. Drug Metab. Pharmacokinet. 2014, 29(2):177-184.
20. FDA, Guidance for Industry-Analytical Procedures and Methods Validation for Drugs and Biologics, 2014.
21. Aubin H.J., Luquiens A., Berlin I. Pharmacotherapy for smoking cessation: pharmacological principles and clinical practice. Br. J. Clin. Pharmacol. 2014, 77(February (2)):324-336.
22. Schroeder D.H. Metabolism and kinetics of bupropion. J. Clin. Psychiatry 1983, 44(May (5 Pt 2)):79-81. (Schroeder).
23. Schroeder D.H. The isolation and identification of some basic urinary metabolites of bupropion-HCL in man. Pharmacologist 1979, 21(3):191.
24. Lai A.A., Schroeder D.H. Clinical pharmacokinetics of bupropion: a review. J. Clin. Psychiatry 1983, 44(May (5 Pt 2)):82-84.
25. Posner J., Bye A., Dean K., Peck A.W., Whiteman P.D. The disposition of bupropion and its metabolites in healthy male volunteers after single and multiple doses. Eur. J. Clin. Pharmacol. 1985, 29(1):97-103.
26. Laizure S.C., DeVane C.L., Stewart J.T., Dommisse C.S., Lai A.A. Pharmacokinetics of bupropion and its major basic metabolites in normal subjects after a single Dose. Clin. Pharmacol. Ther. 1985, 38(November (5)):586-589.
27. Findlay J.W., Van Wyck Fleet J., Smith P.G., Butz R.F., Hinton M.L., Blum M.R., Schroeder D.H. Pharmacokinetics of bupropion, a novel antidepressant agent, following oral administration to healthy subjects. Eur. J. Clin. Pharmacol. 1981, 21(2):127-135.
28. Silverstone P.H., Williams R., McMahon L., Fleming R., Fogarty S. Convulsive liability of bupropion hydrochloride metabolites in Swiss albino mice. Ann. Gen. Psychiatry 2008, 7(October):19.
29. Kharasch E.D., Mitchell D., Coles R. Stereoselective bupropion hydroxylation as an in vivo phenotypic probe for cytochrome P4502B6 (CYP2B6) activity. J. Clin. Pharmacol. 2008, 48(April (4)):464-474.
30. Turpeinen M., Raunio H., Pelkonen O. The functional role of CYP2B6 in human drug metabolism: substrates and inhibitors in vitro, in vivo and in silico. Curr. Drug Metab. 2006, 7:705-714.
31. Desta Z., Saussele T., Ward B., Blievernicht J., Li L., Klein K., Flockhart D.A., Zanger U.M. Impact of CYP2B6 polymorphism on hepatic efavirenz metabolism in vitro. Pharmacogenomics 2007, 8:547-558.
32. Turpeinen M., Tolonen A., Uusitalo J., Jalonen J., Pelkonen O., Laine K. Effect of clopidogrel and ticlopidine on cytochrome P450 2B6 activity as measured by bupropion hydroxylation. Clin. Pharmacol. Ther. 2005, 77(June (6)):553-559.
33. Zhang Y., Huo M., Zhou J., Xie S. PKSolver: an add-in program for pharmacokinetic and pharmacodynamic data analysis in Microsoft Excel. Comput. Methods Programs Biomed. 2016, 99(3):306-314.