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Xenobiotica
the fate of foreign compounds in biological systems
Volume 17, 1987 - Issue 3
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Original Article

Pharmacological significance of the species differences in bupropion metabolism

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Pages 287-298 | Published online: 30 Sep 2009

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Rafaela Costa, Nuno G. Oliveira & Ricardo Jorge Dinis-Oliveira. (2019) Pharmacokinetic and pharmacodynamic of bupropion: integrative overview of relevant clinical and forensic aspects. Drug Metabolism Reviews 51:3, pages 293-313.
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Jillissa C. Molnari & Alan L. Myers. (2012) Carbonyl reduction of bupropion in human liver. Xenobiotica 42:6, pages 550-561.
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Yuan Chen, Hua-fen Liu, Liling Liu, Khanh Nguyen, Elliott B. Jones & Adrian J. Fretland. (2010) The in vitro metabolism of bupropion revisited: concentration dependent involvement of cytochrome P450 2C19. Xenobiotica 40:8, pages 536-546.
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Articles from other publishers (61)

Chandrali S. Bhattacharya, Andrea R. Masters, Christine Bach, Anthony L. Sinn, Melissa A. Trowbridge & Robert E. StratfordJr.Jr.. (2023) Characterization of the Stereoselective Disposition of Bupropion and Its Metabolites in Rat Plasma and Brain. European Journal of Drug Metabolism and Pharmacokinetics 48:2, pages 171-187.
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Nadia O Bamfo, Jessica BL Lu & Zeruesenay Desta. (2023) Stereoselective Metabolism of Bupropion to Active Metabolites in Cellular Fractions of Human Liver and Intestine. Drug Metabolism and Disposition 51:1, pages 54-66.
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Donald J. AbrahamRichard A. Glennon & Leslie Iversen. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 1 56 .
Pan-Fen Wang, Alicia Neiner & Evan D. Kharasch. (2020) Stereoselective Bupropion Hydroxylation by Cytochrome P450 CYP2B6 and Cytochrome P450 Oxidoreductase Genetic Variants. Drug Metabolism and Disposition 48:6, pages 438-445.
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Montserrat Navarro, Kendall L. Luhn, Alexey B. Kampov‐Polevoy, James C. Garbutt & Todd E. Thiele. (2019) Bupropion, Alone and in Combination with Naltrexone, Blunts Binge‐Like Ethanol Drinking and Intake Following Chronic Intermittent Access to Ethanol in Male C57 BL /6J Mice . Alcoholism: Clinical and Experimental Research 43:5, pages 783-790.
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Chandrali Bhattacharya, Danielle Kirby, Michael Van Stipdonk & Robert E. Stratford. (2018) Comparison of In Vitro Stereoselective Metabolism of Bupropion in Human, Monkey, Rat, and Mouse Liver Microsomes. European Journal of Drug Metabolism and Pharmacokinetics 44:2, pages 261-274.
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Emily R. Nicholson, Julian E. Dilley & Janice C. Froehlich. (2018) Co-Administration of Low-Dose Naltrexone and Bupropion Reduces Alcohol Drinking in Alcohol-Preferring (P) Rats. Alcoholism: Clinical and Experimental Research 42:3, pages 571-577.
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Eunice Yuen, Steven Swanson & Jeffrey M. Witkin. (2017) Prediction of human efficacious antidepressant doses using the mouse forced swim test. Pharmacology Biochemistry and Behavior 161, pages 22-29.
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John A. Rosecrans & Richard Young. 2018. The Behavioral Neuroscience of Drug Discrimination. The Behavioral Neuroscience of Drug Discrimination 51 94 .
Jennifer E. Sager, John R. Choiniere, Justine Chang, Alyssa Stephenson-Famy, Wendel L. Nelson & Nina Isoherranen. (2016) Identification and Structural Characterization of Three New Metabolites of Bupropion in Humans. ACS Medicinal Chemistry Letters 7:8, pages 791-796.
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Aaron M. Teitelbaum, Alicia M. Flaker & Evan D. Kharasch. (2016) Development, validation and application of a comprehensive stereoselective LC/MS–MS assay for bupropion and oxidative, reductive, and glucuronide metabolites in human urine. Journal of Chromatography B 1027, pages 239-253.
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A. R. Masters, B. T. Gufford, J. B. L. Lu, I. F. Metzger, D. R. Jones & Z. Desta. (2016) Chiral Plasma Pharmacokinetics and Urinary Excretion of Bupropion and Metabolites in Healthy Volunteers. Journal of Pharmacology and Experimental Therapeutics 358:2, pages 230-238.
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Sonika Batra & Ravi Bhushan. (2015) Resolution of enantiomers of bupropion and its metabolites by liquid chromatography. Biomedical Chromatography 30:5, pages 670-682.
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B. T. Gufford, J. B. L. Lu, I. F. Metzger, D. R. Jones & Z. Desta. (2016) Stereoselective Glucuronidation of Bupropion Metabolites In Vitro and In Vivo. Drug Metabolism and Disposition 44:4, pages 544-553.
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E. Malcolm, F. I. Carroll, B. Blough, M. I. Damaj & M. Shoaib. (2015) Examination of the metabolite hydroxybupropion in the reinforcing and aversive stimulus effects of nicotine in rats. Psychopharmacology 232:15, pages 2763-2771.
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Anne K. Laib, Sonja Brünen, Philippe Pfeifer, Philippe Vincent & Christoph Hiemke. (2014) Serum Concentrations of Hydroxybupropion for Dose Optimization of Depressed Patients Treated With Bupropion. Therapeutic Drug Monitoring 36:4, pages 473-479.
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Jiake He, Yang Yu, Bhagwat Prasad, Xijing Chen & Jashvant D. Unadkat. (2014) Mechanism of an unusual, but clinically significant, digoxin-bupropion drug interaction. Biopharmaceutics & Drug Disposition 35:5, pages 253-263.
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F. Ivy Carroll, Bruce E. Blough, S. Wayne Mascarella, Hernán A. Navarro, Ronald J. Lukas & M. Imad Damaj. 2014. Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse 177 216 .
Rohit Bansal, Balraj Saini, Yogita Bansal & Gulshan Bansal. (2013) MS n , LC-MS-TOF and LC-PDA studies for identification of new degradation impurities of bupropion . Biomedical Chromatography 27:11, pages 1387-1397.
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Eric Sands. 2014. Handbook of Metabolic Pathways of Xenobiotics. Handbook of Metabolic Pathways of Xenobiotics 1 3 .
Arne Meyer, Anna Vuorinen, Agnieszka E. Zielinska, Petra Strajhar, Gareth G. Lavery, Daniela Schuster & Alex Odermatt. (2013) Formation of Threohydrobupropion from Bupropion Is Dependent on 11 β -Hydroxysteroid Dehydrogenase 1 . Drug Metabolism and Disposition 41:9, pages 1671-1678.
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Katarina Ilic, Roy L. Hawke, Ranjit K. Thirumaran, Erin G. Schuetz, J. Heyward Hull, Angela D.M. Kashuba, Paul W. Stewart, Celeste M. Lindley & Mei-Ling Chen. (2013) The Influence of Sex, Ethnicity, and CYP2B6 Genotype on Bupropion Metabolism as an Index of Hepatic CYP2B6 Activity in Humans . Drug Metabolism and Disposition 41:3, pages 575-581.
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S. D. Grabus, F. I. Carroll & M. I. Damaj. (2012) Bupropion and its Main Metabolite Reverse Nicotine Chronic Tolerance in the Mouse. Nicotine & Tobacco Research 14:11, pages 1356-1361.
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Samah S. Abbas, Mohamed R. Elghobashy, Rafeek F. Shokry & Lories I. Bebawy. (2012) Stability indicating HPLC and spectrophotometric methods for the determination of bupropion hydrochloride in the presence of its alkaline degradates and related impurity. Bulletin of Faculty of Pharmacy, Cairo University 50:1, pages 49-59.
Crossref
Jillissa C. Molnari, Hazem E. Hassan & Alan L. Myers. (2011) Effects of sertraline on the pharmacokinetics of bupropion and its major metabolite, hydroxybupropion, in mice. European Journal of Drug Metabolism and Pharmacokinetics 37:1, pages 57-63.
Crossref
Alexander V. LyubimovDeepak K. Dalvie. 2011. Encyclopedia of Drug Metabolism and Interactions. Encyclopedia of Drug Metabolism and Interactions 1 54 .
Dumrongsak Pekthong, Coraline Desbans, Hélène Martin & Lysiane Richert. (2012) Bupropion Hydroxylation as a Selective Marker of Rat CYP2B1 Catalytic Activity. Drug Metabolism and Disposition 40:1, pages 32-38.
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Jillissa Christine Molnari, Hazem EmadEldin Hassan, Bryant Michael Moeller & Alan Lewis Myers. (2011) Drug Interaction Study between Bupropion and Ticlopidine in Male CF-1 Mice. Biological and Pharmaceutical Bulletin 34:3, pages 447-451.
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Bartłomiej Barczyński, Grzegorz Buszewicz, Jarogniew J. Łuszczki, Krzysztof Bańka, Krzysztof Tutaj, Tomasz Mróz, Marian Wielosz, Roman Mądro & Piotr Tutka. (2011) Low dose of bupropion significantly enhances the anticonvulsant activity of felbamate, lamotrigine and topiramate in mice. European Journal of Pharmacology 650:2-3, pages 550-555.
Crossref
Robert E. Sorge & Paul B. S. Clarke. 2011. Animal Models of Drug Addiction. Animal Models of Drug Addiction 101 132 .
Paul M. O’Byrne, Robert Williams, John J. Walsh & John F. Gilmer. (2010) The aqueous stability of bupropion. Journal of Pharmaceutical and Biomedical Analysis 53:3, pages 376-381.
Crossref
Donald J. AbrahamRichard A. Glennon & Leslie Iversen. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 219 264 .
M. Imad Damaj, Sheri D. Grabus, Hernan A. Navarro, Robert E. Vann, Jonathan A. Warner, Lindsey S. King, Jenny L. Wiley, Bruce E. Blough, Ronald J. Lukas & F. Ivy Carroll. (2010) Effects of Hydroxymetabolites of Bupropion on Nicotine Dependence Behavior in Mice. Journal of Pharmacology and Experimental Therapeutics 334:3, pages 1087-1095.
Crossref
Trevor Grinter. 2010. Green Chemistry in the Pharmaceutical Industry. Green Chemistry in the Pharmaceutical Industry 197 219 .
Leah M Hesse, Yumiko Sakai, Daesety Vishnuvardhan, Albert P Li, Lisa L von Moltke & David J Greenblatt. (2003) Effect of bupropion on CYP2B6 and CYP3A4 catalytic activity, immunoreactive protein and mRNA levels in primary human hepatocytes: comparison with rifampicin. Journal of Pharmacy and Pharmacology 55:9, pages 1229-1239.
Crossref
Neil E. Paterson. (2009) Behavioural and pharmacological mechanisms of bupropion's anti-smoking effects: Recent preclinical and clinical insights. European Journal of Pharmacology 603:1-3, pages 1-11.
Crossref
Peter H Silverstone, Robert Williams, Louis McMahon, Rosanna Fleming & Siobhan Fogarty. (2008) Convulsive liability of bupropion hydrochloride metabolites in Swiss albino mice. Annals of General Psychiatry 7:1.
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Robert L. Walsky & R. Scott Obach. (2007) A Comparison of 2-Phenyl-2-(1-piperidinyl)propane (PPP), 1,1′,1″-Phosphinothioylidynetrisaziridine (ThioTEPA), Clopidogrel, and Ticlopidine as Selective Inactivators of Human Cytochrome P450 2B6. Drug Metabolism and Disposition 35:11, pages 2053-2059.
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Anna M. Lee, Christopher Jepson, Ewa Hoffmann, Leonard Epstein, Larry W. Hawk, Caryn Lerman & Rachel F. Tyndale. (2007) CYP2B6 Genotype Alters Abstinence Rates in a Bupropion Smoking Cessation Trial. Biological Psychiatry 62:6, pages 635-641.
Crossref
Aleksanteri Petsalo, Miia Turpeinen & Ari Tolonen. (2007) Identification of bupropion urinary metabolites by liquid chromatography/mass spectrometry. Rapid Communications in Mass Spectrometry 21:16, pages 2547-2554.
Crossref
Jean-Noël Volle, Nikolay Kaloyanov, Mohamed Chiheb Saada, David Virieux & Jean-Luc Pirat. (2007) Phosphinyl analogues of hydroxybupropion: (±)-2-aryl-3,3,5,5-tetramethyl-[1,4,2]-oxazaphosphinanes. Tetrahedron Letters 48:27, pages 4695-4697.
Crossref
Sonja K Billes & Michael A Cowley. (2006) Inhibition of Dopamine and Norepinephrine Reuptake Produces Additive Effects on Energy Balance in Lean and Obese Mice. Neuropsychopharmacology 32:4, pages 822-834.
Crossref
Hongmei Xu, Katarzyna K. Loboz, Annette S. Gross & Andrew J. McLachlan. (2006) Stereoselective analysis of hydroxybupropion and application to drug interaction studies. Chirality 19:3, pages 163-170.
Crossref
Linda P. Dwoskin, Anthony S. Rauhut, Kelley A. King‐Pospisil & Michael T. Bardo. (2007) Review of the Pharmacology and Clinical Profile of Bupropion, an Antidepressant and Tobacco Use Cessation Agent. CNS Drug Reviews 12:3-4, pages 178-207.
Crossref
Jean-Noël Volle, David Virieux, Matthieu Starck, Jérôme Monbrun, Ludovic Clarion & Jean-Luc Pirat. (2006) Chiral phosphinyl analogues of 2-C-arylmorpholinols: 2-aryl-3,5-diphenyl-[1,4,2]-oxazaphosphinanes. Tetrahedron: Asymmetry 17:9, pages 1402-1408.
Crossref
Aberra Fura. (2006) Role of pharmacologically active metabolites in drug discovery and development. Drug Discovery Today 11:3-4, pages 133-142.
Crossref
Katarzyna K. Loboz, Annette S. Gross, John Ray & Andrew J. McLachlan. (2005) HPLC assay for bupropion and its major metabolites in human plasma. Journal of Chromatography B 823:2, pages 115-121.
Crossref
M. Imad Damaj, F. Ivy Carroll, J. Brek Eaton, Hernan A. Navarro, Bruce E. Blough, Sadiq Mirza, Ronald J. Lukas & Billy R. Martin. (2004) Enantioselective Effects of Hydroxy Metabolites of Bupropion on Behavior and on Function of Monoamine Transporters and Nicotinic Receptors. Molecular Pharmacology 66:3, pages 675-682.
Crossref
Richard A. Glennon. 2004. 55 123 .
Mikhail L Bondarev, Tatiana S Bondareva, Richard Young & Richard A Glennon. (2003) Behavioral and biochemical investigations of bupropion metabolites. European Journal of Pharmacology 474:1, pages 85-93.
Crossref
Donald J. AbrahamLeslie Iversen & Richard A. Glennon. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 483 524 .
Richard Young & Richard A. Glennon. (2002) Nicotine and bupropion share a similar discriminative stimulus effect. European Journal of Pharmacology 443:1-3, pages 113-118.
Crossref
Simon Xi-Ming Li, Kenneth W Perry & David T Wong. (2002) Influence of fluoxetine on the ability of bupropion to modulate extracellular dopamine and norepinephrine concentrations in three mesocorticolimbic areas of rats. Neuropharmacology 42:2, pages 181-190.
Crossref
Qun K Fang, Zhengxu Han, Paul Grover, Donald Kessler, Chris H Senanayake*Stephen A Wald. (2000) Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate. Tetrahedron: Asymmetry 11:18, pages 3659-3663.
Crossref
G. Evan Boswell, David L. Musso, Ann O. Davis, James L. Kelley, Francis E. Soroko & Barret R. Cooper. (2009) Synthesis, stereochemistry and anti‐tetrabenazine activity of bicyclo analogues of 2‐phenylmorpholines. Journal of Heterocyclic Chemistry 34:6, pages 1813-1820.
Crossref
Raymond F. Suckow, Ming F. Zhang & Thomas B. Cooper. (1997) Enantiomeric Determination of the Phenylmorpholinol Metabolite of Bupropion in Human Plasma Using Coupled Achiral-Chiral Liquid Chromatography. Biomedical Chromatography 11:3, pages 174-179.
Crossref
James L. Kelley, David L. Musso, G. Evan Boswell, Francis E. Soroko & Barrett R. Cooper. (1996) (2 S ,3 S ,5 R )-2-(3,5-Difluorophenyl)-3,5- dimethyl-2-morpholinol:  A Novel Antidepressant Agent and Selective Inhibitor of Norepinephrine Uptake . Journal of Medicinal Chemistry 39:2, pages 347-349.
Crossref
Terence A. Ketter, Janice B. Jenkins, David H. Schroeder, Peggy J. Pazzaglia, Lauren B. Marangell, Mark S. George, Ann M. Callahan, Melvin L. Hinton, John Chao & Robert M. Post. (1995) Carbamazepine but not Valproate Induces Bupropion Metabolism. Journal of Clinical Psychopharmacology 15:5, pages 327-333.
Crossref
G. Laux, A. Delini-Stula, U. Breyer-Pfaff, J. Demling, D. Ebert, W. Pöldinger, S. Kasper, M. Osterheider, O. Dietmaier, H.-J. Möller & J. Fuger. 1993. Neuro-Psychopharmaka. Neuro-Psychopharmaka 105 268 .
John A. Hill & Jeffrey D. Scharver. (2006) Syntheses of carbon‐14 and tritium labelled forms of bupropion hydrochloride – a novel antidepressant. Journal of Labelled Compounds and Radiopharmaceuticals 25:10, pages 1095-1104.
Crossref
Juzar S. Kaka, Khalil I. Al-Khamis & Musbah O. M. Tanira. (1988) Effect of hepatic and renal dysfunction on disposition of Bupropion in rats. European Journal of Drug Metabolism and Pharmacokinetics 13:3, pages 149-153.
Crossref

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