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Volumn 82, Issue 7, 2011, Pages 789-796

Preparation of human drug metabolites using fungal peroxygenases

Author keywords

Cytochrome P450; Hydroxylation; N Dealkylation; O Dealkylation; Peroxidase; Peroxygenation

Indexed keywords

ACETANILIDE; ALIPHATIC COMPOUND; AMINOPHENAZONE; AROMATIC COMPOUND; AROMATIC PEROXYGENASE; CARBAMAZEPINE; CHLORPROMAZINE; CORTODOXONE; DEUTERIUM; DEXTRORPHAN; DICLOFENAC; DRUG METABOLITE; ETHINYLESTRADIOL; FELBAMATE; FUNGAL ENZYME; GEMFIBROZIL; HYDROGEN PEROXIDE; IBUPROFEN; KETOPROFEN; LIDOCAINE; METOPROLOL; NAPROXEN; OMEPRAZOLE; OSELTAMIVIR; PHENACETIN; PROPRANOLOL; SILDENAFIL; SULFADIAZINE; TAMOXIFEN; TOLBUTAMIDE; UNCLASSIFIED DRUG;

EID: 80051795192     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.06.020     Document Type: Article
Times cited : (66)

References (69)
  • 1
    • 0020325715 scopus 로고
    • Metabolic activation and drug toxicity
    • DOI 10.1021/jm00349a001
    • S.D. Nelson Metabolic activation and drug toxicity J Med Chem 25 1982 753 765 (Pubitemid 12056951)
    • (1982) Journal of Medicinal Chemistry , vol.25 , Issue.7 , pp. 753-765
    • Nelson, S.D.1
  • 3
    • 34250716024 scopus 로고    scopus 로고
    • Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-α-pyrrolidinobutyrophenone
    • DOI 10.1016/j.bcp.2007.05.010, PII S000629520700319X
    • F.T. Peters, C.A. Dragan, D.R. Wilde, M.R. Meyer, J. Zapp, and M. Bureik Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-alpha-pyrrolidinobutyrophenone Biochem Pharmacol 74 2007 511 520 (Pubitemid 46963243)
    • (2007) Biochemical Pharmacology , vol.74 , Issue.3 , pp. 511-520
    • Peters, F.T.1    Dragan, C.-A.2    Wilde, D.R.3    Meyer, M.R.4    Zapp, J.5    Bureik, M.6    Maurer, H.H.7
  • 5
    • 33846979487 scopus 로고    scopus 로고
    • Enzymatic hydroxylation of aromatic compounds
    • DOI 10.1007/s00018-007-6362-1
    • R. Ullrich, and M. Hofrichter Enzymatic hydroxylation of aromatic compounds Cell Mol Life Sci 64 2007 271 293 (Pubitemid 46440205)
    • (2007) Cellular and Molecular Life Sciences , vol.64 , Issue.3 , pp. 271-293
    • Ullrich, R.1    Hofrichter, M.2
  • 6
    • 50049104412 scopus 로고    scopus 로고
    • Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase
    • M. Kinne, R. Ullrich, K.E. Hammel, K. Scheibner, and M. Hofrichter Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase Tetrahedron Lett 49 2008 5950 5953
    • (2008) Tetrahedron Lett , vol.49 , pp. 5950-5953
    • Kinne, M.1    Ullrich, R.2    Hammel, K.E.3    Scheibner, K.4    Hofrichter, M.5
  • 8
    • 33746021124 scopus 로고    scopus 로고
    • Preparative use of isolated CYP102 monooxygenases-A critical appraisal
    • DOI 10.1016/j.jbiotec.2006.02.013, PII S0168165606001787
    • S. Eiben, L. Kaysser, S. Maurer, K. Kuhnel, V.B. Urlacher, and R.D. Schmid Preparative use of isolated CYP102 monooxygenases - a critical appraisal J Biotechnol 124 2006 662 669 (Pubitemid 44066594)
    • (2006) Journal of Biotechnology , vol.124 , Issue.4 , pp. 662-669
    • Eiben, S.1    Kaysser, L.2    Maurer, S.3    Kuhnel, K.4    Urlacher, V.B.5    Schmid, R.D.6
  • 9
    • 32544436092 scopus 로고    scopus 로고
    • Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450
    • DOI 10.1002/bit.20744
    • C.R. Otey, G. Bandara, J. Lalonde, K. Takahashi, and F.H. Arnold Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450 Biotechnol Bioeng 93 2006 494 499 (Pubitemid 43232175)
    • (2006) Biotechnology and Bioengineering , vol.93 , Issue.3 , pp. 494-499
    • Otey, C.R.1    Bandara, G.2    Lalonde, J.3    Takahashi, K.4    Arnold, F.H.5
  • 10
    • 70350518093 scopus 로고    scopus 로고
    • A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds
    • A.M. Sawayama, M.M. Chen, P. Kulanthaivel, M.S. Kuo, H. Hemmerle, and F.H. Arnold A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds Chemistry 15 2009 11723 11729
    • (2009) Chemistry , vol.15 , pp. 11723-11729
    • Sawayama, A.M.1    Chen, M.M.2    Kulanthaivel, P.3    Kuo, M.S.4    Hemmerle, H.5    Arnold, F.H.6
  • 11
    • 0029664872 scopus 로고    scopus 로고
    • 2-catalyzed aromatic hydroxylation proceeds by a cytochrome-P-450-type oxygen-transfer reaction mechanism
    • 2-catalyzed aromatic hydroxylation proceeds by a cytochrome-P-450-type oxygen-transfer reaction mechanism Eur J Biochem 240 1996 232 238 (Pubitemid 26276776)
    • (1996) European Journal of Biochemistry , vol.240 , Issue.1 , pp. 232-238
    • Osman, A.M.1
  • 12
    • 0037173591 scopus 로고    scopus 로고
    • Does P450-type catalysis proceed through a peroxo-iron intermediate? A review of studies with microperoxidase
    • DOI 10.1016/S0162-0134(02)00393-8, PII S0162013402003938
    • C. Veeger Does P450-type catalysis proceed through a peroxo-iron intermediate?. A review of studies with microperoxidase J Inorg Biochem 91 2002 35 45 (Pubitemid 34741941)
    • (2002) Journal of Inorganic Biochemistry , vol.91 , Issue.1 , pp. 35-45
    • Veeger, C.1
  • 17
    • 65149103447 scopus 로고    scopus 로고
    • Regioselective preparation of 5-hydroxypropranolol and 4′-hydroxydiclofenac with a fungal peroxygenase
    • M. Kinne, M. Poraj-Kobielska, E. Aranda, R. Ullrich, K.E. Hammel, and K. Scheibner Regioselective preparation of 5-hydroxypropranolol and 4′-hydroxydiclofenac with a fungal peroxygenase Bioorg Med Chem Lett 19 2009 3085 3087
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 3085-3087
    • Kinne, M.1    Poraj-Kobielska, M.2    Aranda, E.3    Ullrich, R.4    Hammel, K.E.5    Scheibner, K.6
  • 22
    • 63949083769 scopus 로고    scopus 로고
    • Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases
    • E. Aranda, M. Kinne, M. Kluge, R. Ullrich, and M. Hofrichter Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases Appl Microbiol Biotechnol 82 2008 1057 1066
    • (2008) Appl Microbiol Biotechnol , vol.82 , pp. 1057-1066
    • Aranda, E.1    Kinne, M.2    Kluge, M.3    Ullrich, R.4    Hofrichter, M.5
  • 23
    • 77950459712 scopus 로고    scopus 로고
    • Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases
    • E. Aranda, R. Ullrich, and M. Hofrichter Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases Biodegradation 21 2009 267 281
    • (2009) Biodegradation , vol.21 , pp. 267-281
    • Aranda, E.1    Ullrich, R.2    Hofrichter, M.3
  • 24
    • 0017328569 scopus 로고
    • Quantitative determination of phenacetin and its metabolite acetaminophen by GLC-chemical ionization mass spectrometry
    • W.A. Garland, K.C. Hsiao, E.J. Pantuck, and A.H. Conney Quantitative determination of phenacetin and its metabolite acetaminophen by GLC-chemical ionization mass spectrometry J Pharm Sci 66 1977 340 344 (Pubitemid 8076222)
    • (1977) Journal of Pharmaceutical Sciences , vol.66 , Issue.3 , pp. 340-344
    • Garland, W.A.1    Hsiao, K.C.2    Pantuck, E.J.3    Conney, A.H.4
  • 26
    • 4143095883 scopus 로고    scopus 로고
    • Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes
    • DOI 10.1128/AEM.70.8.4575-4581.2004
    • R. Ullrich, J. Nüske, K. Scheibner, J. Spantzel, and M. Hofrichter Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes Appl Environ Microbiol 70 2004 4575 4581 (Pubitemid 39095478)
    • (2004) Applied and Environmental Microbiology , vol.70 , Issue.8 , pp. 4575-4581
    • Ullrich, R.1    Nuske, J.2    Scheibner, K.3    Spantzel, J.4    Hofrichter, M.5
  • 27
    • 34548508886 scopus 로고    scopus 로고
    • The coprophilous mushroom Coprinus radians secretes a haloperoxidase that catalyzes aromatic peroxygenation
    • DOI 10.1128/AEM.00026-07
    • D.H. Anh, R. Ullrich, D. Benndorf, A. Svatos, A. Muck, and M. Hofrichter The coprophilous mushroom Coprinus radians secretes a haloperoxidase that catalyzes aromatic peroxygenation Appl Environ Microbiol 73 2007 5477 5485 (Pubitemid 47378751)
    • (2007) Applied and Environmental Microbiology , vol.73 , Issue.17 , pp. 5477-5485
    • Dau, H.A.1    Ullrich, R.2    Benndorf, D.3    Svatos, A.4    Muck, A.5    Hofrichter, M.6
  • 28
    • 0031856715 scopus 로고    scopus 로고
    • An EXCEL template for calculation of enzyme kinetic parameters by non-linear regression
    • A. Hernandez, and M.T. Ruiz An EXCEL template for calculation of enzyme kinetic parameters by non-linear regression Bioinformatics 14 1998 227 228 (Pubitemid 28395883)
    • (1998) Bioinformatics , vol.14 , Issue.2 , pp. 227-228
    • Hernandez, A.1    Ruiz, M.T.2
  • 29
    • 0028020099 scopus 로고
    • Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes: The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N- desisopropylase
    • Y. Masubuchi, S. Hosokawa, T. Horie, T. Suzuki, S. Ohmori, and M. Kitada Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase Drug Metab Dispos 22 1994 909 915 (Pubitemid 24377367)
    • (1994) Drug Metabolism and Disposition , vol.22 , Issue.6 , pp. 909-915
    • Masubuchi, Y.1    Hosokawa, S.2    Horie, T.3    Suzuki, T.4    Ohmori, S.5    Kitada, M.6    Narimatsu, S.7
  • 30
    • 0029737485 scopus 로고    scopus 로고
    • Use of tolbutamide as a substrate probe for human hepatic cytochrome P450 2C9
    • J.O. Miners, and D.J. Birkett Use of tolbutamide as a substrate probe for human hepatic cytochrome P450 2C9 Methods Enzymol 272 1996 139 145 (Pubitemid 26299876)
    • (1996) Methods in Enzymology , vol.272 , pp. 139-145
    • Miners, J.O.1    Birkett, D.J.2
  • 31
    • 0029916692 scopus 로고    scopus 로고
    • Cytochromes P450, 1A2, and 2C9 are responsible for the human hepatic O-demethylation of R- and S-naproxen
    • J.O. Miners, S. Coulter, R.H. Tukey, M.E. Veronese, and D.J. Birkett Cytochromes P450, 1A2, and 2C9 are responsible for the human hepatic O-demethylation of R- and S-naproxen Biochem Pharmacol 51 1996 1003 1008
    • (1996) Biochem Pharmacol , vol.51 , pp. 1003-1008
    • Miners, J.O.1    Coulter, S.2    Tukey, R.H.3    Veronese, M.E.4    Birkett, D.J.5
  • 32
    • 0026008585 scopus 로고
    • Role of cytochrome P450 IA2 in acetanilide 4-hydroxylation as determined with cDNA expression and monoclonal antibodies
    • G. Liu, H.V. Gelboin, and M.J. Myers Role of cytochrome P450 IA2 in acetanilide 4-hydroxylation as determined with cDNA expression and monoclonal antibodies Arch Biochem Biophys 284 1991 400 406
    • (1991) Arch Biochem Biophys , vol.284 , pp. 400-406
    • Liu, G.1    Gelboin, H.V.2    Myers, M.J.3
  • 33
    • 44149107346 scopus 로고    scopus 로고
    • The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil
    • DOI 10.1124/dmd.107.020099
    • H.Y. Ku, H.J. Ahn, K.A. Seo, H. Kim, M. Oh, and S.K. Bae The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil Drug Metab Dispos 36 2008 986 990 (Pubitemid 351717478)
    • (2008) Drug Metabolism and Disposition , vol.36 , Issue.6 , pp. 986-990
    • Ku, H.-Y.1    Ahn, H.-J.2    Seo, K.-A.3    Kim, H.4    Oh, M.5    Soo, K.B.6    Shin, J.-G.7    Shon, J.-H.8    Liu, K.-H.9
  • 35
    • 0023664534 scopus 로고
    • Oxidative cleavage of carboxylic esters by cytochrome P-450
    • F.P. Guengerich Oxidative cleavage of carboxylic esters by cytochrome P-450 J Biol Chem 262 1987 8459 8462
    • (1987) J Biol Chem , vol.262 , pp. 8459-8462
    • Guengerich, F.P.1
  • 37
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity
    • F.P. Guengerich Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity Chem Res Toxicol 14 2001 611 650 (Pubitemid 32565712)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.6 , pp. 611-650
    • Guengerich, F.P.1
  • 39
    • 78149373621 scopus 로고    scopus 로고
    • Cytochrome P450 compound I: Capture, characterization, and C-H bond activation kinetics
    • J. Rittle, and M.T. Green Cytochrome P450 compound I: capture, characterization, and C-H bond activation kinetics Science 330 2010 933 937
    • (2010) Science , vol.330 , pp. 933-937
    • Rittle, J.1    Green, M.T.2
  • 40
    • 0034687092 scopus 로고    scopus 로고
    • Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants
    • C.H. Yun, G.P. Miller, and F.P. Guengerich Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants Biochemistry 39 2000 11319 11329
    • (2000) Biochemistry , vol.39 , pp. 11319-11329
    • Yun, C.H.1    Miller, G.P.2    Guengerich, F.P.3
  • 41
    • 0034740665 scopus 로고    scopus 로고
    • a and distribution coefficient in the metabolism of fluorinated propranolol derivatives. Preparation, identification of metabolite regioisomers, and metabolism by CYP2D6
    • a and distribution coefficient in the metabolism of fluorinated propranolol derivatives. Preparation, identification of metabolite regioisomers, and metabolism by CYP2D6 Drug Metab Dispos 29 2001 1377 1388 (Pubitemid 33000683)
    • (2001) Drug Metabolism and Disposition , vol.29 , Issue.11 , pp. 1377-1388
    • Upthagrove, A.L.1    Nelson, W.L.2
  • 42
    • 70349422251 scopus 로고    scopus 로고
    • A diversified library of bacterial and fungal bifunctional cytochrome P450 enzymes for drug metabolite synthesis
    • R. Weis, M. Winkler, M. Schittmayer, S. Kambourakis, M. Vink, and J.D. Rozzell A diversified library of bacterial and fungal bifunctional cytochrome P450 enzymes for drug metabolite synthesis Adv Synth Catal 351 2009 2140 2146
    • (2009) Adv Synth Catal , vol.351 , pp. 2140-2146
    • Weis, R.1    Winkler, M.2    Schittmayer, M.3    Kambourakis, S.4    Vink, M.5    Rozzell, J.D.6
  • 43
    • 73449104732 scopus 로고    scopus 로고
    • Purification of homogeneous forms of fungal peroxygenase
    • R. Ullrich, C. Liers, S. Schimpke, and M. Hofrichter Purification of homogeneous forms of fungal peroxygenase Biotechnol J 4 2009 1619 1626
    • (2009) Biotechnol J , vol.4 , pp. 1619-1626
    • Ullrich, R.1    Liers, C.2    Schimpke, S.3    Hofrichter, M.4
  • 45
    • 77953151732 scopus 로고    scopus 로고
    • Crystallization of a 45 kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron
    • K. Piontek, R. Ullrich, C. Liers, K. Diederichs, D.A. Plattner, and M. Hofrichter Crystallization of a 45 kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron Acta Crystallogr Sect F Struct Biol Cryst Commun 66 2010 693 698
    • (2010) Acta Crystallogr Sect F Struct Biol Cryst Commun , vol.66 , pp. 693-698
    • Piontek, K.1    Ullrich, R.2    Liers, C.3    Diederichs, K.4    Plattner, D.A.5    Hofrichter, M.6
  • 46
    • 0015117843 scopus 로고
    • Pharmacology of 4-hydroxypropranolol, a metabolite of propranolol
    • J.D. Fitzgerald, and S.R. O'Donnell Pharmacology of 4-hydroxypropranolol, a metabolite of propranolol Br J Pharmacol 43 1971 222 235
    • (1971) Br J Pharmacol , vol.43 , pp. 222-235
    • Fitzgerald, J.D.1    O'Donnell, S.R.2
  • 47
    • 37549019074 scopus 로고
    • The metabolic fate of acetanilid and other aniline derivates
    • L.A. Greenberg, and D. Lester The metabolic fate of acetanilid and other aniline derivates J Pharmacol Exp Ther 88 1946 87 98
    • (1946) J Pharmacol Exp Ther , vol.88 , pp. 87-98
    • Greenberg, L.A.1    Lester, D.2
  • 48
    • 0025848751 scopus 로고
    • Evidence for the involvement of several cytochromes P-450 in the first steps of caffeine metabolism by human liver microsomes
    • F. Berthou, J.P. Flinois, D. Ratanasavanh, P. Beaune, C. Riche, and A. Guillouzo Evidence for the involvement of several cytochromes P-450 in the first steps of caffeine metabolism by human liver microsomes Drug Metab Dispos 19 1991 561 567
    • (1991) Drug Metab Dispos , vol.19 , pp. 561-567
    • Berthou, F.1    Flinois, J.P.2    Ratanasavanh, D.3    Beaune, P.4    Riche, C.5    Guillouzo, A.6
  • 49
    • 0035009420 scopus 로고    scopus 로고
    • Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology
    • DOI 10.1016/S0887-2333(01)00011-X, PII S088723330100011X
    • S. Yoshitomi, K. Ikemoto, J. Takahashi, H. Miki, M. Namba, and S. Asahi Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology Toxicol In Vitro 15 2001 245 256 (Pubitemid 32476834)
    • (2001) Toxicology in Vitro , vol.15 , Issue.3 , pp. 245-256
    • Yoshitomi, S.1    Ikemoto, K.2    Takahashi, J.3    Miki, H.4    Namba, M.5    Asahi, S.6
  • 50
    • 0036841947 scopus 로고    scopus 로고
    • Pathways of carbamazepine bioactivation in vitro I. Characterization of human cytochromes P450 responsible for the formation of 2- and 3-hydroxylated metabolites
    • DOI 10.1124/dmd.30.11.1170
    • R.E. Pearce, G.R. Vakkalagadda, and J.S. Leeder Pathways of carbamazepine bioactivation in vitro. I. Characterization of human cytochromes P450 responsible for the formation of 2- and 3-hydroxylated metabolites Drug Metab Dispos 30 2002 1170 1179 (Pubitemid 35265822)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.11 , pp. 1170-1179
    • Pearce, R.E.1    Vakkalagadda, G.R.2    Steven Leeder, J.3
  • 51
    • 0032797632 scopus 로고    scopus 로고
    • Hepatic metabolism of diclofenac: Role of human CYP in the minor oxidative pathways
    • DOI 10.1016/S0006-2952(99)00167-7, PII S0006295299001677
    • R. Bort, K. Macé, A. Boobis, M.-J. Gómez-Lechón, A. Pfeifer, and J. Castell Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways Biochem Pharmacol 58 1999 787 796 (Pubitemid 29329528)
    • (1999) Biochemical Pharmacology , vol.58 , Issue.5 , pp. 787-796
    • Bort, R.1    MacE, K.2    Boobis, A.3    Gomez-Lechon, M.-J.4    Pfeifer, A.5    Castell, J.6
  • 53
    • 19944434201 scopus 로고    scopus 로고
    • CYP2D6 Genotype, antidepressant use, and tamoxifen metabolism during adjuvant breast cancer treatment
    • Y. Jin, Z. Desta, V. Stearns, B. Ward, H. Ho, and K.-H. Lee CYP2D6 Genotype, antidepressant use, and tamoxifen metabolism during adjuvant breast cancer treatment J Natl Cancer Inst 97 2005 30 39
    • (2005) J Natl Cancer Inst , vol.97 , pp. 30-39
    • Jin, Y.1    Desta, Z.2    Stearns, V.3    Ward, B.4    Ho, H.5    Lee, K.-H.6
  • 56
    • 0030857031 scopus 로고    scopus 로고
    • Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C
    • DOI 10.1016/S0006-2952(97)00143-3, PII S0006295297001433
    • M.A. Hamman, G.A. Thompson, and S.D. Hall Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C Biochem Pharmacol 54 1997 33 41 (Pubitemid 27353220)
    • (1997) Biochemical Pharmacology , vol.54 , Issue.1 , pp. 33-41
    • Hamman, M.A.1    Thompson, G.A.2    Hall, S.D.3
  • 58
    • 0032698375 scopus 로고    scopus 로고
    • Quantitative determination of tolbutamide and its metabolites in human plasma and urine by high-performance liquid chromatography and UV detection
    • L.L. Hansen, and K. Brøsen Quantitative determination of tolbutamide and its metabolites in human plasma and urine by high-performance liquid chromatography and UV detection Ther Drug Monit 21 1999 664
    • (1999) Ther Drug Monit , vol.21 , pp. 664
    • Hansen, L.L.1    Brøsen, K.2
  • 59
    • 0023625981 scopus 로고
    • Analysis of α-hydroxy metabolites of metoprolol in human urine after phosgene/trimethylsilyl derivatization
    • K.-J. Hoffmann, O. Gyllenhaal, and J. Vessman Analysis of α-hydroxy metabolites of metoprolol in human urine after phosgene/trimethylsilyl derivatization Biol Mass Spectrom 14 1987 543 548 (Pubitemid 18060762)
    • (1987) Biomedical and Environmental Mass Spectrometry , vol.14 , Issue.10 , pp. 543-548
    • Hoffmann, K.-J.1    Gyllenhaal, O.2    Vessman, J.3
  • 60
    • 0016637864 scopus 로고
    • Naproxen metabolism in man
    • E.J. Segre Naproxen metabolism in man J Clin Pharmacol 15 1975 316 323
    • (1975) J Clin Pharmacol , vol.15 , pp. 316-323
    • Segre, E.J.1
  • 61
    • 0035877976 scopus 로고    scopus 로고
    • Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen
    • D. Bougie, and R. Aster Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen Blood 97 2001 3846 3850
    • (2001) Blood , vol.97 , pp. 3846-3850
    • Bougie, D.1    Aster, R.2
  • 62
    • 0027265750 scopus 로고
    • CYP2D6- and CYP3A-dependent metabolism of dextromethorphan in humans
    • E. Jacqz-Aigrain, C. Funck-Brentano, and T. Cresteil CYP2D6- and CYP3A-dependent metabolism of dextromethorphan in humans Pharmacogenetics 3 1993 197 204 (Pubitemid 23265487)
    • (1993) Pharmacogenetics , vol.3 , Issue.4 , pp. 197-204
    • Jacqz-Aigrain, E.1    Funck-Brentano, C.2    Cresteil, T.3
  • 63
    • 0024359553 scopus 로고
    • Effect of quinidine on the dextromethorphan O-demethylase activity of microsomal fractions from human liver
    • F. Broly, C. Libersa, M. Lhermitte, P. Bechtel, and B. Dupuis Effect of quinidine on the dextromethorphan O-demethylase activity of microsomal fractions from human liver Br J Clin Pharmacol 28 1989 29 36 (Pubitemid 19195662)
    • (1989) British Journal of Clinical Pharmacology , vol.28 , Issue.1 , pp. 29-36
    • Broly, F.1    Libersa, C.2    Lhermitte, M.3    Bechtel, P.4    Dupuis, B.5
  • 64
    • 0002489339 scopus 로고
    • The fate of acetophenetidin (phenacetin) in man and methods for the estimation of acetophenetidin and its metabolites in biological material
    • B.B. Brodie, and J. Axelrod The fate of acetophenetidin (phenacetin) in man and methods for the estimation of acetophenetidin and its metabolites in biological material J Pharmacol Exp Ther 97 1949 58 67
    • (1949) J Pharmacol Exp Ther , vol.97 , pp. 58-67
    • Brodie, B.B.1    Axelrod, J.2
  • 65
    • 4143147349 scopus 로고    scopus 로고
    • Discovering drugs through biological transformation: Role of pharmacologically active metabolites in drug discovery
    • DOI 10.1021/jm040066v
    • A. Fura, Y.-Z. Shu, M. Zhu, R.L. Hanson, V. Roongta, and W.G. Humphreys Discovering drugs through biological transformation: role of pharmacologically active metabolites in drug discovery J Med Chem 47 2004 4339 4351 (Pubitemid 39096823)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.18 , pp. 4339-4351
    • Fura, A.1    Shu, Y.-Z.2    Zhu, M.3    Hanson, R.L.4    Roongta, V.5    Humphreys, W.G.6
  • 66
    • 0035039489 scopus 로고    scopus 로고
    • Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil
    • DOI 10.1046/j.1365-2125.2001.00318.x
    • R. Hyland, E.G.H. Roe, B.C. Jones, and D.A. Smith Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil Br J Clin Pharmacol 51 2001 239 248 (Pubitemid 32391501)
    • (2001) British Journal of Clinical Pharmacology , vol.51 , Issue.3 , pp. 239-248
    • Hyland, R.1    Roe, E.G.H.2    Jones, B.C.3    Smith, D.A.4
  • 68
    • 0014089679 scopus 로고
    • Excretion of aminopyrine and its metabolites into cows' milk
    • N.C. Banerjee, G.E. Miller, and C.M. Stowe Excretion of aminopyrine and its metabolites into cows' milk Toxicol Appl Pharmacol 10 1967 604 612
    • (1967) Toxicol Appl Pharmacol , vol.10 , pp. 604-612
    • Banerjee, N.C.1    Miller, G.E.2    Stowe, C.M.3
  • 69
    • 0035096415 scopus 로고    scopus 로고
    • Oseltamivir: A review of its use in influenza
    • K. McClellan, and C.M. Perry Oseltamivir: a review of its use in influenza Drugs 61 2001 263 283 (Pubitemid 32210201)
    • (2001) Drugs , vol.61 , Issue.2 , pp. 263-283
    • McClellan, K.1    Perry, C.M.2


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