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Volumn 25, Issue 3, 2012, Pages 572-583

Alternate strategies to obtain mass balance without the use of radiolabeled compounds: Application of quantitative fluorine ( 19F) Nuclear Magnetic Resonance (NMR) spectroscopy in metabolism studies

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; DRUG METABOLITE; FLUORINE;

EID: 84863338113     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx2005629     Document Type: Article
Times cited : (30)

References (53)
  • 1
    • 19444365324 scopus 로고    scopus 로고
    • Application of LC/MS, LC/NMR and Stable Isotopes in Identifying and Characterizing Metabolites
    • Lee, J. S., Obach, R. S., and Fisher, M. B., Eds Fontis Media and Marcel Dekker, New York, NY
    • Mutlib, A. E., and Shockcor, J. P. (2003) Application of LC/MS, LC/NMR and Stable Isotopes in Identifying and Characterizing Metabolites, in Drug Metabolizing Enzymes: Cytochrome P450 and Other Enzymes in Drug Discovery and Development (Lee, J. S., Obach, R. S., and Fisher, M. B., Eds) pp 33-86 Fontis Media and Marcel Dekker, New York, NY.
    • (2003) Drug Metabolizing Enzymes: Cytochrome P450 and Other Enzymes in Drug Discovery and Development , pp. 33-86
    • Mutlib, A.E.1    Shockcor, J.P.2
  • 2
    • 3943099892 scopus 로고    scopus 로고
    • High resolution NMR of biomolecules
    • Prestgard, J. H. (2001) High resolution NMR of biomolecules. Lecture Notes Phys. 595, 426-434.
    • (2001) Lecture Notes Phys. , vol.595 , pp. 426-434
    • Prestgard, J.H.1
  • 4
    • 12944265405 scopus 로고    scopus 로고
    • 1H NMR: Development and potential of a method for natural products analysis
    • DOI 10.1021/np0497301
    • Pauli, G. F., Jaki, B., and Lankin, D. (2005) Quantitative 1H-NMR: Development and potential of a method for natural products analysis. J. Nat. Prod. 68, 133-149. (Pubitemid 40175949)
    • (2005) Journal of Natural Products , vol.68 , Issue.1 , pp. 133-149
    • Pauli, G.F.1    Jaki, B.U.2    Lankin, D.C.3
  • 5
    • 34249102874 scopus 로고    scopus 로고
    • A routine experimental protocol for qHNMR illustrated with taxol
    • DOI 10.1021/np060535r
    • Pauli, G. F., Jaki, B. U., and Lankin, D. C. (2007) A routine experimental protocol for qHNMR illustrated with Taxol. J. Nat. Prod. 70, 589-595. (Pubitemid 46797861)
    • (2007) Journal of Natural Products , vol.70 , Issue.4 , pp. 589-595
    • Pauli, G.F.1    Jaki, B.U.2    Lankin, D.C.3
  • 7
    • 0022311713 scopus 로고
    • 19F nuclear magnetic resonance
    • Bernadou, J., Armand, J. P., Lopez, A., Malet-Martino, M. C., and Martino, R. (1985) Complete urinary excretion profile of 5- fluorouracil during a six-day chemotherapeutic schedule, as resolved by 19F nuclear magnetic resonance. Clin. Chem. 31, 846-848. (Pubitemid 16140534)
    • (1985) Clinical Chemistry , vol.31 , Issue.6 , pp. 846-848
    • Bernadou, J.1    Armand, J.P.2    Lopez, A.3
  • 8
    • 0027394560 scopus 로고
    • Determination of the urinary excretion of ifosfamide and its phosphorated metabolites by phosphorus-31 nuclear magnetic resonance spectroscopy
    • DOI 10.1007/BF00686153
    • Gilard, V., Malet-Martino, M. C., De Forni, M., Niemeyer, U., Ader, J. C., and Martino, R. (1993) Determination of the urinary excretion of ifosfamide and its phosporated metabolites by phosphorus-31 nuclear magnetic resonance spectroscopy. Cancer Chemother. Pharmacol. 31, 387-394. (Pubitemid 23045652)
    • (1993) Cancer Chemotherapy and Pharmacology , vol.31 , Issue.5 , pp. 387-394
    • Gilard, V.1    Malet-Martino, M.C.2    De Forni, M.3    Niemeyer, U.4    Ader, J.C.5    Martino, R.6
  • 9
    • 0026491216 scopus 로고
    • Magnetic resonance spectroscopy: A powerful tool for drug metabolism studies
    • Malet-Martino, M. C., and Martino, R. (1992) Magnetic resonance spectroscopy: a powerful tool for drug metabolism studies. Biochimie 74, 785-800.
    • (1992) Biochimie , vol.74 , pp. 785-800
    • Malet-Martino, M.C.1    Martino, R.2
  • 10
    • 0036182507 scopus 로고    scopus 로고
    • 1H-NMR spectroscopy
    • DOI 10.1002/nbm.740
    • Le Belle, J. E., Harris, N. G, Williams, S. R., and Bhakoo, K. K. (2002) A comparison of cell and tissue extraction techniques using high-resolution 1H-NMR spectroscopy. NMR Biomed. 15, 37-44. (Pubitemid 34177166)
    • (2002) NMR in Biomedicine , vol.15 , Issue.1 , pp. 37-44
    • Le, B.J.E.1    Harris, N.G.2    Williams, S.R.3    Bhakoo, K.K.4
  • 11
    • 0036533298 scopus 로고    scopus 로고
    • A comparison of quantitative NMR and radiolabelling studies of the metabolism and excretion of Statil (3-(4-bromo-2-fluorobenzyl)-4-oxo-3H- phthalazin-1-ylacetic acid) in the rat
    • DOI 10.1016/S0731-7085(01)00637-9, PII S0731708501006379
    • Lenz, E. M., Wilson, I. D., Wright, B., Partridge, E. A., Rodgers, C. T., Haycock, P. R., Lindon, J. C., and Nicholson, J. K. (2002) A comparison of quantitative NMR and radiolabelling studies of the metabolism and excretion of Statil (3-(4-bromo-2-fluorobenzyl)-4-oxo-3H-phthalazin-1-ylacetic acid) in the rat. J. Pharm. Biomed. Anal. 28, 31-43. (Pubitemid 34171644)
    • (2002) Journal of Pharmaceutical and Biomedical Analysis , vol.28 , Issue.1 , pp. 31-43
    • Lenz, E.M.1    Wilson, I.D.2    Wright, B.3    Partridge, E.A.4    Rodgers, C.T.5    Haycock, P.R.6    Lindon, J.C.7    Nicholson, J.K.8
  • 12
    • 11244288218 scopus 로고    scopus 로고
    • 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism
    • DOI 10.1080/00498250412331281098
    • Skordi, E., Wilson, I. D., Lindon, J. C., and Nicholson, J. K. (2004) Characterization and quantification of metabolites of racemic ketoprofen excreted in urine following oral administration to man by 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism. Xenobiotica 24, 1075-1089. (Pubitemid 40070107)
    • (2004) Xenobiotica , vol.34 , Issue.11-12 , pp. 1075-1089
    • Skordi, E.1    Wilson, I.D.2    Lindon, J.C.3    Nicholson, J.K.4
  • 13
    • 23644433986 scopus 로고    scopus 로고
    • Fluorine-19 or phosphorus-31 NMR spectroscopy: A suitable analytical technique for quantitative in vitro metabolic studies of fluorinated or phosphorylated drugs
    • DOI 10.1016/j.jpba.2005.01.047, PII S0731708505001652
    • Martino, R., Gilard, V., Desmoulin, F., and Malet-Martino, M. (2005) Fluorine-19 or phosphorus-31 NMR spectroscopy: A suitable analytical technique for quantitative in vitro metabolic studies of fluorinated or phosphorylated drugs. J. Pharm. Biomed. Anal. 38, 871-891. (Pubitemid 41115794)
    • (2005) Journal of Pharmaceutical and Biomedical Analysis , vol.38 , Issue.5 SPEC. ISS. , pp. 871-891
    • Martino, R.1    Gilard, V.2    Desmoulin, F.3    Malet-Martino, M.4
  • 14
    • 34247168396 scopus 로고    scopus 로고
    • Quantitative NMR analysis of a sesamin catechol metabolite in human urine
    • Moazzami, A. A., Anderson, R. E., and Kamal-Eldin, A. (2007) Quantitative NMR analysis of a sesamin catechol metabolite in human urine. J. Nutr. 137, 940-944. (Pubitemid 46596891)
    • (2007) Journal of Nutrition , vol.137 , Issue.4 , pp. 940-944
    • Moazzami, A.A.1    Andersson, R.E.2    Kamal-Eldin, A.3
  • 15
    • 0035870167 scopus 로고    scopus 로고
    • Determination of substrate and product concentrations in lactic acid bacterial fermentations by proton NMR using the ERETIC method
    • DOI 10.1021/ac0013204
    • Silvestre, V., Goupry, S., Trierweiler, M., Robins, R., and Akoka, S. (2001) Determination of substrate and product concentrations in lactic acid bacterial fermentations by proton NMR using the ERETIC method. Anal. Chem. 73, 1862-1868. (Pubitemid 32862454)
    • (2001) Analytical Chemistry , vol.73 , Issue.8 , pp. 1862-1868
    • Silvestre, V.1    Goupry, S.2    Trierweiler, M.3    Robins, R.4    Akoka, S.5
  • 16
    • 0036138810 scopus 로고    scopus 로고
    • Quantitative NMR spectroscopy using coaxial inserts containing a reference standard: Purity determinations for military nerve agents
    • Henderson, T. J. (2002) Quantitative NMR spectroscopy using coaxial inserts containing a reference standard: Purity determinations for military nerve agents. Anal. Chem. 74, 191-198.
    • (2002) Anal. Chem. , vol.74 , pp. 191-198
    • Henderson, T.J.1
  • 17
    • 27844543753 scopus 로고    scopus 로고
    • Proton nuclear magnetic resonance spectroscopy (NMR) methods for determining the purity of reference drug standards and illicit forensic drug seizures
    • Hays, P. A. (2005) Proton nuclear magnetic resonance spectroscopy (NMR) methods for determining the purity of reference drug standards and illicit forensic drug seizures. J. Forensic Sci. 50, 1342-1360.
    • (2005) J. Forensic Sci. , vol.50 , pp. 1342-1360
    • Hays, P.A.1
  • 18
    • 34547111855 scopus 로고    scopus 로고
    • NMR Spectroscopy of Biofluids
    • Robertson, D. G., and Lindon, J., Eds. Taylor and Francis, Boca Raton, FL
    • Lindon, J. C., Nicholson, J. K., and Holmes, E. (2005) NMR Spectroscopy of Biofluids, in Metabonomics in Toxicity Assessment (Robertson, D. G., and Lindon, J., Eds.) pp 105-172, Taylor and Francis, Boca Raton, FL.
    • (2005) Metabonomics in Toxicity Assessment , pp. 105-172
    • Lindon, J.C.1    Nicholson, J.K.2    Holmes, E.3
  • 19
    • 34548065372 scopus 로고    scopus 로고
    • Recent developments and applications of NMR-based metabonomics
    • Lindon, J. C., Holmes, E., and Nicholson, J. K. (2006) Recent developments and applications of NMR-based metabonomics. Bopuxue Zazhi 23, 101-127.
    • (2006) Bopuxue Zazhi , vol.23 , pp. 101-127
    • Lindon, J.C.1    Holmes, E.2    Nicholson, J.K.3
  • 20
    • 84996430922 scopus 로고    scopus 로고
    • Metabonomics
    • Taylor, J. B., and Triggle, D. J., Eds. Elsevier, Oxford, U.K.
    • Wilson, I. D., and Nicholson, J. K. (2006) Metabonomics, in Comprehensive Medicinal Chemistry II (Taylor, J. B., and Triggle, D. J., Eds.) pp 989-1007, Elsevier, Oxford, U.K.
    • (2006) Comprehensive Medicinal Chemistry II , pp. 989-1007
    • Wilson, I.D.1    Nicholson, J.K.2
  • 21
    • 0034760549 scopus 로고    scopus 로고
    • Quantitative NMR spectroscopy
    • Evilia, R. F. (2001) Quantitative NMR spectroscopy. Anal. Lett. 34, 2227-2236.
    • (2001) Anal. Lett. , vol.34 , pp. 2227-2236
    • Evilia, R.F.1
  • 22
  • 23
    • 18844378856 scopus 로고    scopus 로고
    • 1H NMR with external standards: Use in preparation of calibration solutions for algal toxins and other natural products
    • DOI 10.1021/ac048385h
    • Burton, I. W., Quilliam, M. A., and Walter, J. A. (2005) Quantitative 1H-NMR with external standards: Use in preparation of calibration solutions for algal toxins and other natural products. Anal. Chem. 77, 3123-3131. (Pubitemid 40695467)
    • (2005) Analytical Chemistry , vol.77 , Issue.10 , pp. 3123-3131
    • Burton, I.W.1    Quilliam, M.A.2    Walter, J.A.3
  • 24
    • 53549097600 scopus 로고    scopus 로고
    • U. S. Food and Drug Administration Center for Drug Evaluation and Research (CDER)
    • U. S. Food and Drug Administration (2008) Guidance for Industry Safety Testing of Drug Metabolites, Center for Drug Evaluation and Research (CDER).
    • (2008) Guidance for Industry Safety Testing of Drug Metabolites
  • 26
    • 56549113149 scopus 로고    scopus 로고
    • Evaluation of preparative high performance liquid chromatography and cryoprobe-nuclear magnetic resonance spectroscopy for the early quantitative estimation of drug metabolites in human plasma
    • Dear, G. J., Roberts, A. D., Beaumont, C., and North, S. E. (2008) Evaluation of preparative high performance liquid chromatography and cryoprobe-nuclear magnetic resonance spectroscopy for the early quantitative estimation of drug metabolites in human plasma. J. Chromatogr., B 876, 182-190.
    • (2008) J. Chromatogr., B , vol.876 , pp. 182-190
    • Dear, G.J.1    Roberts, A.D.2    Beaumont, C.3    North, S.E.4
  • 27
    • 62249210251 scopus 로고    scopus 로고
    • Nuclear magnetic resonanace spectroscopy as a quantitative tool to determine the concentrations of biologically produced metabolites: Implications in metabolites in safety testing
    • Espina, R., Yu, L., Wang, J., Tong, Z., Vashishta, S., Talaat, R., Scatina, J., and Mutlib, A. (2009) Nuclear magnetic resonanace spectroscopy as a quantitative tool to determine the concentrations of biologically produced metabolites: Implications in metabolites in safety testing. Chem. Res. Toxicol. 22, 299-310.
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 299-310
    • Espina, R.1    Yu, L.2    Wang, J.3    Tong, Z.4    Vashishta, S.5    Talaat, R.6    Scatina, J.7    Mutlib, A.8
  • 28
    • 62249117708 scopus 로고    scopus 로고
    • Obtaining exposures of metabolites in preclinical species through plasma pooling and quantitative NMR: Addressing metabolites in safety testing (MIST) guidance without using radiolabeled compounds and chemically synthesized metabolite standards
    • Vishwanathan, K., Babalola, K., Wang, J., Espina, R., Yu, L., Adedoyin, A., Talaat, R., Scatina, J., and Mutlib, A. (2009) Obtaining exposures of metabolites in preclinical species through plasma pooling and quantitative NMR: Addressing metabolites in safety testing (MIST) guidance without using radiolabeled compounds and chemically synthesized metabolite standards. Chem. Res. Toxicol. 22, 311-322.
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 311-322
    • Vishwanathan, K.1    Babalola, K.2    Wang, J.3    Espina, R.4    Yu, L.5    Adedoyin, A.6    Talaat, R.7    Scatina, J.8    Mutlib, A.9
  • 29
    • 0035416421 scopus 로고    scopus 로고
    • Systematic LC/MS metabolite identification in drug discovery
    • Clarke, N. J., Rindgen, D., Korfmacher, W. A., and Cox, K. A. (2001) Systemic LC/MS metabolite identification in drug discovery. Anal. Chem. 73, 430A-439A. (Pubitemid 32862353)
    • (2001) Analytical Chemistry , vol.73 , Issue.15
    • Clarke, N.J.1    Rindgen, D.2    Korfmacher, W.A.3    Cox, K.A.4
  • 30
    • 0242521617 scopus 로고    scopus 로고
    • A software filter to remove interference ions from drug metabolites in accurate mass liquid chromatography/mass spectrometric analyses [1]
    • DOI 10.1002/jms.521
    • Zhang, H., Zhang, D., and Ray, K. (2003) A software filter to remove interference ions from drug metabolites in accurate mass liquid chromatography/mass spectrometric analyses. J. Mass Spectrom. 38, 1110-1112. (Pubitemid 37407706)
    • (2003) Journal of Mass Spectrometry , vol.38 , Issue.10 , pp. 1110-1112
    • Zhang, H.1    Zhang, D.2    Ray, K.3
  • 31
    • 33748902567 scopus 로고    scopus 로고
    • Detection and characterization of metabolites in biological matrices using mass defect filtering of liquid chromatography/high resolution mass spectrometry data
    • DOI 10.1124/dmd.106.009241
    • Zhu, M., Ma, L., Zhang, D., Ray, K., Zhao, W., Humphreys, W. G., Skiles, G., Sanders, M., and Zhang, H. (2006) Detection and characterization of metabolites in biological matrices using mass defect filtering of liquid chromatography/high resolution mass spectrometry data. Drug Metab. Dispos. 34, 1722-1733. (Pubitemid 44427475)
    • (2006) Drug Metabolism and Disposition , vol.34 , Issue.10 , pp. 1722-1733
    • Zhu, M.1    Ma, L.2    Zhang, D.3    Ray, K.4    Zhao, W.5    Humphreys, W.G.6    Skiles, G.7    Sanders, M.8    Zhang, H.9
  • 32
    • 65249152385 scopus 로고    scopus 로고
    • Application of liquid chromatography-accelerator mass spectrometry (LC-AMS) to evaluate the metabolic profiles of a drug candidate in human urine and plasma
    • Prakash, C., Shaffer, C. L., and Tremaine, L. M. (2007) Application of liquid chromatography-accelerator mass spectrometry (LC-AMS) to evaluate the metabolic profiles of a drug candidate in human urine and plasma. Drug Metab. Lett. 1, 226-231.
    • (2007) Drug Metab. Lett. , vol.1 , pp. 226-231
    • Prakash, C.1    Shaffer, C.L.2    Tremaine, L.M.3
  • 33
    • 46849091191 scopus 로고    scopus 로고
    • Mass defect profiles of biological matrices and the general applicability of mass defect filtering for metabolite detection
    • DOI 10.1002/rcm.3585
    • Zhang, H., Zhu, M., Ray, K. L., Ma, L., and Zhang, D. (2008) Mass defect profiles of biological matrices and the general applicability of mass defect filtering for metabolite detection. Rapid Commun. Mass Spectrom. 22, 2082-2088. (Pubitemid 351956694)
    • (2008) Rapid Communications in Mass Spectrometry , vol.22 , Issue.13 , pp. 2082-2088
    • Zhang, H.1    Zhu, M.2    Ray, K.L.3    Ma, L.4    Zhang, D.5
  • 35
  • 36
    • 0034332544 scopus 로고    scopus 로고
    • Fluorine nuclear magnetic resonance, a privileged tool for metabolic studies of fluoropyrimidine drugs
    • Martino, R., Malet-Martino, M., and Gilard, V. (2000) Fluorine nuclear magnetic resonance, a privileged tool for metabolic studies of fluoropyrimidine drugs. Curr. Drug Metab. 1, 271-303.
    • (2000) Curr. Drug Metab. , vol.1 , pp. 271-303
    • Martino, R.1    Malet-Martino, M.2    Gilard, V.3
  • 38
    • 44649122129 scopus 로고    scopus 로고
    • Fluorine magnetic resonance in vivo: A powerful tool in the study of drug distribution and metabolism
    • Reid, D. G., and Murphy, P. S. (2008) Fluorine magnetic resonance in vivo: A powerful tool in the study of drug distribution and metabolism. Drug Discovery Today 13, 473-480.
    • (2008) Drug Discovery Today , vol.13 , pp. 473-480
    • Reid, D.G.1    Murphy, P.S.2
  • 39
    • 0031941954 scopus 로고    scopus 로고
    • 19F magnetic resonance spectroscopy
    • Strauss, W. L., Layton, M. E., and Dager, S. R. (1998) Brain elimination half-life of fluvoxamine measured by 19-F magnetic resonance spectroscopy. Am. J. Psychiatr. 155, 380-384. (Pubitemid 28114896)
    • (1998) American Journal of Psychiatry , vol.155 , Issue.3 , pp. 380-384
    • Strauss, W.L.1    Layton, M.E.2    Dager, S.R.3
  • 40
    • 0033995074 scopus 로고    scopus 로고
    • Monitoring pharmacokinetics of anticancer drugs: Non-invasive investigation using magnetic resonance spectroscopy
    • DOI 10.1016/S0169-409X(99)00057-5, PII S0169409X99000575
    • Griffiths, J. R., and Glickson, J. D. (2000) Monitoring pharmacokinetics of anticancer drugs: non-invasive investigation using magnetic resonance spectroscopy. Adv. Drug Delivery Rev. 41, 75-89. (Pubitemid 30122950)
    • (2000) Advanced Drug Delivery Reviews , vol.41 , Issue.1 , pp. 75-89
    • Griffiths, J.R.1    Glickson, J.D.2
  • 41
    • 33749495245 scopus 로고    scopus 로고
    • MR spectroscopy: Its potential role for drug development for the treatment of psychiatric diseases
    • DOI 10.1002/nbm.1080
    • Mason, G. F., and Krystal, J. H. (2006) MR spectroscopy: its potential role for drug development for the treatment of psychiatric diseases. NMR Biomed. 19, 690-701. (Pubitemid 44515613)
    • (2006) NMR in Biomedicine , vol.19 , Issue.6 , pp. 690-701
    • Mason, G.F.1    Krystal, J.H.2
  • 42
    • 0031593732 scopus 로고    scopus 로고
    • 19F-NMRS of 5-fluorouracil in pharmacokinetics and pharmacodynamic studies
    • DOI 10.1002/(SICI)1099-1492(1998110)11:7<380::AID-NBM517>3.0.CO;2-Q
    • Wolf, W., Waluch, V., and Presant, C. A. (1998) Non-invasive 19-F NMRS of 5-fluorouracil in pharmacokinetics and pharmacodynamics studies. NMR Biomed. 11, 380-387. (Pubitemid 28547373)
    • (1998) NMR in Biomedicine , vol.11 , Issue.7 , pp. 380-387
    • Wolf, W.1    Waluch, V.2    Presant, C.A.3
  • 43
    • 0033623840 scopus 로고    scopus 로고
    • 19-F MRS studies of fluorinated drugs in humans
    • Wolf, W., Presant, C. A., and Waluch, V. (2000) 19-F MRS studies of fluorinated drugs in humans. Adv. Drug Delivery Rev. 41, 56-74.
    • (2000) Adv. Drug Delivery Rev. , vol.41 , pp. 56-74
    • Wolf, W.1    Presant, C.A.2    Waluch, V.3
  • 44
    • 0031596869 scopus 로고    scopus 로고
    • 19F-NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4-trifluoromethylaniline in rat: A urinary excretion balance study without the use of radiolabelling
    • 19F-NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4- trifluoromethylaniline in rat: a urinary excretion balance study without the use of radiolabelling. Xenobiotica 28, 373-388.
    • (1998) Xenobiotica , vol.28 , pp. 373-388
    • Scarf, G.B.1    Wright, B.2    Clayton, E.3    Taylor, S.4    Wilson, I.D.5    Lindon, J.C.6    Nicholson, J.K.7
  • 45
    • 0032970483 scopus 로고    scopus 로고
    • 19F-NMR spectroscopy and directly coupled HPLCNMR-MS
    • 19F-NMR spectroscopy and directly coupled HPLCNMR-MS. Xenobiotica 29, 77-91.
    • (1999) Xenobiotica , vol.29 , pp. 77-91
    • Scarf, G.B.1
  • 48
    • 0038128341 scopus 로고    scopus 로고
    • Metabolism of (S)-5,6-Difluoro-4-cyclopropylethynyl-4-trifluoromethyl-3, 4-dihydro-2(1H)-quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics
    • DOI 10.1124/dmd.31.1.122
    • Chen, H., Chen, W., Gan, L., and Mutlib, A. E. (2003) Metabolism of (S-5,6-difluoro-4-cyclopropylethynyl-4-trifluoromethyl-3,4-dihydro-2(1H) -quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics. Drug Metab. Dispos. 31, 122-132. (Pubitemid 36735266)
    • (2003) Drug Metabolism and Disposition , vol.31 , Issue.1 , pp. 122-132
    • Chen, H.1    Chen, W.2    Gan, L.-S.3    Mutlib, A.E.4
  • 49
    • 0017170592 scopus 로고
    • Quantitative NMR analysis of a four-component mixture of phenylglycine derivatives
    • Warren, R. J., Zarembo, J. E., Staiger, D. B., and Post, A. (1976) Quantitative NMR analysis of a four-component mixture of phenylglycine derivatives. J. Pharm. Sci. 65, 738-740.
    • (1976) J. Pharm. Sci. , vol.65 , pp. 738-740
    • Warren, R.J.1    Zarembo, J.E.2    Staiger, D.B.3    Post, A.4
  • 50
    • 62249177074 scopus 로고    scopus 로고
    • Quantitative NMR-spectroscopic analysis of the compounds of glycerol esters of fatty acids
    • Groen, D., Metternich, H. J., and Schoenfelder, W. (1998) Quantitative NMR-spectroscopic analysis of the compounds of glycerol esters of fatty acids. Lipid 100, 64-69.
    • (1998) Lipid , vol.100 , pp. 64-69
    • Groen, D.1    Metternich, H.J.2    Schoenfelder, W.3
  • 51
    • 23644459107 scopus 로고    scopus 로고
    • Quantitative NMR in synthetic and combinatorial chemistry
    • DOI 10.1016/j.jpba.2005.01.045, PII S0731708505001627
    • Rizzo, V., and Pinciroli, V. (2005) Quantitative NMR in synthetic and combinatorial chemistry. J. Pharm. Biomed. Anal. 38, 851-857. (Pubitemid 41115791)
    • (2005) Journal of Pharmaceutical and Biomedical Analysis , vol.38 , Issue.5 SPEC. ISS. , pp. 851-857
    • Rizzo, V.1    Pinciroli, V.2
  • 52
    • 35948970692 scopus 로고    scopus 로고
    • Quantitative NMR spectroscopy in the quality evaluation of active pharmaceutical ingredients and excipients
    • Diehl, B. W. K., Malz, F., and Holzgrabe, U. (2007) Quantitative NMR spectroscopy in the quality evaluation of active pharmaceutical ingredients and excipients. Spec. Eur. 19, 15-19. (Pubitemid 350074081)
    • (2007) Spectroscopy Europe , vol.19 , Issue.5 , pp. 15-19
    • Diehl, B.W.K.1    Malz, F.2    Holzgrabe, U.3
  • 53
    • 53549106345 scopus 로고    scopus 로고
    • Application of stable isotope-labeled compounds in metabolism and in metabolism-mediated toxicity studies
    • Mutlib, A. E. (2008) Application of stable isotope-labeled compounds in metabolism and in metabolism-mediated toxicity studies. Chem. Res. Toxicol. 21, 1672-1689.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1672-1689
    • Mutlib, A.E.1


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