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Volumn 41, Issue 9, 2013, Pages 1671-1678

Formation of threohydrobupropion from bupropion is dependent on 11β-hydroxysteroid dehydrogenase 1

Author keywords

[No Author keywords available]

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE 1; AMFEBUTAMONE; CARBONYL REDUCTASE; CORTISONE; DRUG; DRUG METABOLITE; ERYTHROHYDROBUPROPION; THREOHYDROBUPROPION; UNCLASSIFIED DRUG;

EID: 84882764500     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.052936     Document Type: Article
Times cited : (28)

References (52)
  • 1
    • 84876752347 scopus 로고    scopus 로고
    • Effect of ketoconazole on the pharmacokinetics of the 11b-hydroxysteroid dehydrogenase type 1 inhibitor abt-384 and its two active metabolites in healthy volunteers: Population analysis of data from a drug-drug interaction study
    • An G, Liu W, Katz DA, Marek G, Awni W, and Dutta S (2013) Effect of ketoconazole on the pharmacokinetics of the 11b-hydroxysteroid dehydrogenase type 1 inhibitor ABT-384 and its two active metabolites in healthy volunteers: population analysis of data from a drug-drug interaction study. Drug Metab Dispos 41: 1035-1045.
    • (2013) Drug Metab Dispos , vol.41 , pp. 1035-1045
    • An, G.1    Liu, W.2    Katz, D.A.3    Marek, G.4    Awni, W.5    Dutta, S.6
  • 2
    • 84870904243 scopus 로고    scopus 로고
    • 11b-hydroxysteroid dehydrogenase type 1 inhibitors: Novel agents for the treatment of metabolic syndrome and obesity-related disorders?
    • Anagnostis P, Katsiki N, Adamidou F, Athyros VG, Karagiannis A, Kita M, and Mikhailidis DP (2013) 11b-Hydroxysteroid dehydrogenase type 1 inhibitors: novel agents for the treatment of metabolic syndrome and obesity-related disorders? Metabolism 62:21-33.
    • (2013) Metabolism , vol.62 , pp. 21-33
    • Anagnostis, P.1    Katsiki, N.2    Adamidou, F.3    Athyros, V.G.4    Karagiannis, A.5    Kita, M.6    Mikhailidis, D.P.7
  • 4
    • 34250791225 scopus 로고    scopus 로고
    • Readjusting the glucocorticoid balance: An opportunity for modulators of 11b-hydroxysteroid dehydrogenase type 1 activity?
    • Atanasov AG and Odermatt A (2007) Readjusting the glucocorticoid balance: an opportunity for modulators of 11b-hydroxysteroid dehydrogenase type 1 activity? Endocr Metab Immune Disord Drug Targets 7:125-140.
    • (2007) Endocr Metab Immune Disord Drug Targets , vol.7 , pp. 125-140
    • Atanasov, A.G.1    Odermatt, A.2
  • 6
    • 11844269814 scopus 로고    scopus 로고
    • Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids
    • Czock D, Keller F, Rasche FM, and Häussler U (2005) Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet 44:61-98.
    • (2005) Clin Pharmacokinet , vol.44 , pp. 61-98
    • Czock, D.1    Keller, F.2    Rasche, F.M.3    Häussler, U.4
  • 9
    • 3843105927 scopus 로고    scopus 로고
    • Appropriate function of 11b-hydroxysteroid dehydrogenase type 1 in the endoplasmic reticulum lumen is dependent on its n-Terminal region sharing similar topological determinants with 50-kda esterase
    • Frick C, Atanasov AG, Arnold P, Ozols J, and Odermatt A (2004) Appropriate function of 11b-hydroxysteroid dehydrogenase type 1 in the endoplasmic reticulum lumen is dependent on its N-Terminal region sharing similar topological determinants with 50-kDa esterase. J Biol Chem 279:31131-31138.
    • (2004) J Biol Chem , vol.279 , pp. 31131-31138
    • Frick, C.1    Atanasov, A.G.2    Arnold, P.3    Ozols, J.4    Odermatt, A.5
  • 14
    • 0034009253 scopus 로고    scopus 로고
    • Bupropion: A review of its use in the management of smoking cessation
    • Holm KJ and Spencer CM (2000) Bupropion: a review of its use in the management of smoking cessation. Drugs 59:1007-1024.
    • (2000) Drugs , vol.59 , pp. 1007-1024
    • Holm, K.J.1    Spencer, C.M.2
  • 15
    • 0032428903 scopus 로고    scopus 로고
    • Mechanisms of action and clinical characteristics of three atypical antidepressants: Venlafaxine, nefazodone, bupropion
    • Horst WD and Preskorn SH (1998) Mechanisms of action and clinical characteristics of three atypical antidepressants: venlafaxine, nefazodone, bupropion. J Affect Disord 51:237-254.
    • (1998) J Affect Disord , vol.51 , pp. 237-254
    • Horst, W.D.1    Preskorn, S.H.2
  • 17
    • 42149162795 scopus 로고    scopus 로고
    • 11b-hydroxysteroid dehydrogenase type 1 (11b-HSD1) inhibitors in type 2 diabetes mellitus and obesity
    • Hughes KA, Webster SP, and Walker BR (2008) 11b-hydroxysteroid dehydrogenase type 1 (11b-HSD1) inhibitors in type 2 diabetes mellitus and obesity. Expert Opin Investig Drugs 17: 481-496.
    • (2008) Expert Opin Investig Drugs , vol.17 , pp. 481-496
    • Hughes, K.A.1    Webster, S.P.2    Walker, B.R.3
  • 18
    • 2442614716 scopus 로고    scopus 로고
    • Human and rodent type 1 11beta-hydroxysteroid dehydrogenases are 7betahydroxycholesterol dehydrogenases involved in oxysterol metabolism
    • Hult M, Elleby B, Shafqat N, Svensson S, Rane A, Jörnvall H, Abrahmsen L, and Oppermann U (2004) Human and rodent type 1 11beta- hydroxysteroid dehydrogenases are 7betahydroxycholesterol dehydrogenases involved in oxysterol metabolism. Cell Mol Life Sci 61: 992-999.
    • (2004) Cell Mol Life Sci , vol.61 , pp. 992-999
    • Hult, M.1    Elleby, B.2    Shafqat, N.3    Svensson, S.4    Rane, A.5    Jörnvall, H.6    Abrahmsen, L.7    Oppermann, U.8
  • 19
    • 0345004847 scopus 로고    scopus 로고
    • Selective inhibition of human type 1 11b-hydroxysteroid dehydrogenase by synthetic steroids and xenobiotics
    • Hult M, Jörnvall H, and Oppermann UC (1998) Selective inhibition of human type 1 11b-hydroxysteroid dehydrogenase by synthetic steroids and xenobiotics. FEBS Lett 441: 25-28.
    • (1998) FEBS Lett , vol.441 , pp. 25-28
    • Hult, M.1    Jörnvall, H.2    Oppermann, U.C.3
  • 22
    • 29144510522 scopus 로고    scopus 로고
    • Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations
    • Jefferson JW, Pradko JF, and Muir KT (2005) Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations. Clin Ther 27:1685-1695.
    • (2005) Clin Ther , vol.27 , pp. 1685-1695
    • Jefferson, J.W.1    Pradko, J.F.2    Muir, K.T.3
  • 23
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones G, Willett P, Glen RC, Leach AR, and Taylor R (1997) Development and validation of a genetic algorithm for flexible docking. J Mol Biol 267:727-748.
    • (1997) J Mol Biol , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 24
    • 58149133711 scopus 로고    scopus 로고
    • Medium-And short-chain dehydrogenase/reductase gene and protein families : The sdr superfamily: Functional and structural diversity within a family of metabolic and regulatory enzymes
    • Kavanagh KL, Jörnvall H, Persson B, and Oppermann U (2008) Medium-And short-chain dehydrogenase/reductase gene and protein families : the SDR superfamily: functional and structural diversity within a family of metabolic and regulatory enzymes. Cell Mol Life Sci 65: 3895-3906.
    • (2008) Cell Mol Life Sci , vol.65 , pp. 3895-3906
    • Kavanagh, K.L.1    Jörnvall, H.2    Persson, B.3    Oppermann, U.4
  • 25
    • 0022344462 scopus 로고
    • Pharmacokinetics of bupropion and its major basic metabolites in normal subjects after a single dose
    • Laizure SC, DeVane CL, Stewart JT, Dommisse CS, and Lai AA (1985) Pharmacokinetics of bupropion and its major basic metabolites in normal subjects after a single dose. Clin Pharmacol Ther 38:586-589.
    • (1985) Clin Pharmacol Ther , vol.38 , pp. 586-589
    • Laizure, S.C.1    DeVane, C.L.2    Stewart, J.T.3    Dommisse, C.S.4    Lai, A.A.5
  • 29
    • 0028175803 scopus 로고
    • 11 B-hydroxysteroid dehydrogenase mediates reductive metabolism of xenobiotic carbonyl compounds
    • Maser E and Bannenberg G (1994) 11 b-hydroxysteroid dehydrogenase mediates reductive metabolism of xenobiotic carbonyl compounds. Biochem Pharmacol 47:1805-1812.
    • (1994) Biochem Pharmacol , vol.47 , pp. 1805-1812
    • Maser, E.1    Bannenberg, G.2
  • 30
    • 0037325532 scopus 로고    scopus 로고
    • Purification, characterization and nnk carbonyl reductase activities of 11b-hydroxysteroid dehydrogenase type 1 from human liver: Enzyme cooperativity and significance in the detoxification of a tobacco-derived carcinogen
    • Maser E, Friebertshäuser J, and Völker B (2003) Purification, characterization and NNK carbonyl reductase activities of 11b-hydroxysteroid dehydrogenase type 1 from human liver: enzyme cooperativity and significance in the detoxification of a tobacco-derived carcinogen. Chem Biol Interact 143-144:435-448.
    • (2003) Chem Biol Interact , vol.143-144 , pp. 435-448
    • Maser, E.1    Friebertshäuser, J.2    Völker, B.3
  • 31
    • 1542675142 scopus 로고    scopus 로고
    • Tissue-specific glucocorticoid reactivating enzyme, 11 b-hydroxysteroid dehydrogenase type 1 (11 b-hsd1)-A promising drug target for the treatment of metabolic syndrome
    • Masuzaki H and Flier JS (2003) Tissue-specific glucocorticoid reactivating enzyme, 11 b-hydroxysteroid dehydrogenase type 1 (11 b-HSD1)-A promising drug target for the treatment of metabolic syndrome. Curr Drug Targets Immune Endocr Metabol Disord 3:255-262.
    • (2003) Curr Drug Targets Immune Endocr Metabol Disord , vol.3 , pp. 255-262
    • Masuzaki, H.1    Flier, J.S.2
  • 33
    • 84860559111 scopus 로고    scopus 로고
    • Carbonyl reduction of bupropion in human liver
    • Molnari JC and Myers AL (2012) Carbonyl reduction of bupropion in human liver. Xenobiotica 42:550-561.
    • (2012) Xenobiotica , vol.42 , pp. 550-561
    • Molnari, J.C.1    Myers, A.L.2
  • 34
    • 39349102358 scopus 로고    scopus 로고
    • Hexose-6-phosphate dehydrogenase modulates 11b-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto-And 7b-hydroxy-neurosteroids
    • Nashev LG, Chandsawangbhuwana C, Balazs Z, Atanasov AG, Dick B, Frey FJ, Baker ME, and Odermatt A (2007) Hexose-6-phosphate dehydrogenase modulates 11b-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto-And 7b-hydroxy-neurosteroids. PLoS ONE 2:e561.
    • (2007) PLoS ONE , vol.2
    • Nashev, L.G.1    Chandsawangbhuwana, C.2    Balazs, Z.3    Atanasov, A.G.4    Dick, B.5    Frey, F.J.6    Baker, M.E.7    Odermatt, A.8
  • 36
    • 84856335862 scopus 로고    scopus 로고
    • Tissue-specific modulation of mineralocorticoid receptor function by 11b-hydroxysteroid dehydrogenases: An overview
    • Odermatt A and Kratschmar DV (2012) Tissue-specific modulation of mineralocorticoid receptor function by 11b-hydroxysteroid dehydrogenases: an overview. Mol Cell Endocrinol 350: 168-186.
    • (2012) Mol Cell Endocrinol , vol.350 , pp. 168-186
    • Odermatt, A.1    Kratschmar, D.V.2
  • 37
    • 76749116526 scopus 로고    scopus 로고
    • The glucocorticoid-Activating enzyme 11b-hydroxysteroid dehydrogenase type 1 has broad substrate specificity: Physiological and toxicological considerations
    • Odermatt A and Nashev LG (2010) The glucocorticoid-Activating enzyme 11b-hydroxysteroid dehydrogenase type 1 has broad substrate specificity: Physiological and toxicological considerations. J Steroid Biochem Mol Biol 119:1-13.
    • (2010) J Steroid Biochem Mol Biol , vol.119 , pp. 1-13
    • Odermatt, A.1    Nashev, L.G.2
  • 38
    • 0031021249 scopus 로고    scopus 로고
    • Active site directed mutagenesis of 3 b/17 b-hydroxysteroid dehydrogenase establishes differential effects on short-chain dehydrogenase/reductase reactions
    • Oppermann UC, Filling C, Berndt KD, Persson B, Benach J, Ladenstein R, and Jörnvall H (1997) Active site directed mutagenesis of 3 b/17 b-hydroxysteroid dehydrogenase establishes differential effects on short-chain dehydrogenase/reductase reactions. Biochemistry 36:34-40.
    • (1997) Biochemistry , vol.36 , pp. 34-40
    • Oppermann, U.C.1    Filling, C.2    Berndt, K.D.3    Persson, B.4    Benach, J.5    Ladenstein, R.6    Jörnvall, H.7
  • 39
    • 0141706942 scopus 로고    scopus 로고
    • Inhibition of cytochrome p450 2b6 activity by hormone replacement therapy and oral contraceptive as measured by bupropion hydroxylation
    • Palovaara S, Pelkonen O, Uusitalo J, Lundgren S, and Laine K (2003) Inhibition of cytochrome P450 2B6 activity by hormone replacement therapy and oral contraceptive as measured by bupropion hydroxylation. Clin Pharmacol Ther 74:326-333.
    • (2003) Clin Pharmacol Ther , vol.74 , pp. 326-333
    • Palovaara, S.1    Pelkonen, O.2    Uusitalo, J.3    Lundgren, S.4    Laine, K.5
  • 40
    • 1842611742 scopus 로고    scopus 로고
    • Hormonal responses during prolonged exercise are influenced by a selective da/na reuptake inhibitor
    • Piacentini MF, Meeusen R, Buyse L, De Schutter G, and De Meirleir K (2004) Hormonal responses during prolonged exercise are influenced by a selective DA/NA reuptake inhibitor. Br J Sports Med 38:129-133.
    • (2004) Br J Sports Med , vol.38 , pp. 129-133
    • Piacentini, M.F.1    Meeusen, R.2    Buyse, L.3    De Schutter, G.4    De Meirleir, K.5
  • 41
    • 10044279468 scopus 로고    scopus 로고
    • Effect of bupropion on nocturnal urinary free cortisol and its association with antidepressant response
    • Rao U, Ott GE, Lin KM, Gertsik L, and Poland RE (2005) Effect of bupropion on nocturnal urinary free cortisol and its association with antidepressant response. J Psychiatr Res 39:183-190.
    • (2005) J Psychiatr Res , vol.39 , pp. 183-190
    • Rao, U.1    Ott, G.E.2    Lin, K.M.3    Gertsik, L.4    Poland, R.E.5
  • 43
    • 0020526594 scopus 로고
    • Metabolism and kinetics of bupropion
    • Schroeder DH (1983) Metabolism and kinetics of bupropion. J Clin Psychiatry 44:79-81.
    • (1983) J Clin Psychiatry , vol.44 , pp. 79-81
    • Schroeder, D.H.1
  • 44
    • 2442513350 scopus 로고    scopus 로고
    • Rapid hepatic metabolism of 7-ketocholesterol by 11b-hydroxysteroid dehydrogenase type 1: Species-specific differences between the rat, human, and hamster enzyme
    • Schweizer RA, Zürcher M, Balazs Z, Dick B, and Odermatt A (2004) Rapid hepatic metabolism of 7-ketocholesterol by 11b-hydroxysteroid dehydrogenase type 1: species-specific differences between the rat, human, and hamster enzyme. J Biol Chem 279:18415-18424.
    • (2004) J Biol Chem , vol.279 , pp. 18415-18424
    • Schweizer, R.A.1    Zürcher, M.2    Balazs, Z.3    Dick, B.4    Odermatt, A.5
  • 46
    • 84875448220 scopus 로고    scopus 로고
    • Discovery of sar184841, a potent and long-lasting inhibitor of 11b-hydroxysteroid dehydrogenase type 1, active in a physiopathological animal model of t2d
    • Venier O, Pascal C, Braun A, Namane C, Mougenot P, Crespin O, Pacquet F, Mougenot C, Monseau C, and Onofri B, et al. (2013) Discovery of SAR184841, a potent and long-lasting inhibitor of 11b-hydroxysteroid dehydrogenase type 1, active in a physiopathological animal model of T2D. Bioorg Med Chem Lett 23:2414-2421.
    • (2013) Bioorg Med Chem Lett , vol.23 , pp. 2414-2421
    • Venier, O.1    Pascal, C.2    Braun, A.3    Namane, C.4    Mougenot, P.5    Crespin, O.6    Pacquet, F.7    Mougenot, C.8    Monseau, C.9    Onofri, B.10
  • 50
    • 0023119211 scopus 로고
    • Pharmacological significance of the species differences in bupropion metabolism
    • Welch RM, Lai AA, and Schroeder DH (1987) Pharmacological significance of the species differences in bupropion metabolism. Xenobiotica 17:287-298.
    • (1987) Xenobiotica , vol.17 , pp. 287-298
    • Welch, R.M.1    Lai, A.A.2    Schroeder, D.H.3
  • 51
    • 0031046241 scopus 로고    scopus 로고
    • 11 B-hydroxysteroid dehydrogenase and the syndrome of apparent mineralocorticoid excess
    • White PC, Mune T, and Agarwal AK (1997) 11 b-Hydroxysteroid dehydrogenase and the syndrome of apparent mineralocorticoid excess. Endocr Rev 18:135-156.
    • (1997) Endocr Rev , vol.18 , pp. 135-156
    • White, P.C.1    Mune, T.2    Agarwal, A.K.3
  • 52
    • 0345073742 scopus 로고    scopus 로고
    • Stereochemical aspects of carbonyl reduction of the original anticancer drug oracin by mouse liver microsomes and purified 11b-hydroxysteroid dehydrogenase type 1
    • Wsól V, Szotáková B, Skálová L, and Maser E (2003) Stereochemical aspects of carbonyl reduction of the original anticancer drug oracin by mouse liver microsomes and purified 11b-hydroxysteroid dehydrogenase type 1. Chem Biol Interact 143-144:459-468.
    • (2003) Chem Biol Interact , vol.143-144 , pp. 459-468
    • Wsól, V.1    Szotáková, B.2    Skálová, L.3    Maser, E.4


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