Application of quantitative NMR in pharmacological evaluation of biologically generated metabolites: Implications in drug discovery

Drug Metabolism and Disposition

Volumn 39, Issue 1, 2011, Pages 106-116

  Mutlib, Abdul ^a   Espina, Robert ^a   Vishwanathan, Karthick ^a   Babalola, Kathlene ^a   Chen, Zecheng ^a   Dehnhardt, Christoph ^a   Venkatesan, Aranapakam ^a   Mansour, Tarek ^a   Chaudhary, Inder ^a   Talaat, Rasmy ^a   Scatina, Jo Ann ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE;

ARTICLE; DECISION MAKING; DRUG ACTIVITY; DRUG DEVELOPMENT; DRUG ISOLATION; DRUG RESEARCH; HUMAN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; DRUG DISCOVERY; DRUG EVALUATION, PRECLINICAL; HUMANS; MACACA FASCICULARIS; MAGNETIC RESONANCE IMAGING; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICROSOMES, LIVER; PHARMACEUTICAL PREPARATIONS; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650733730     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.032490     Document Type: Article

References (43)

1. 1H NMR with external standards: use in preparation of calibration solutions for algal toxins and other natural products. Anal Chem 77:3123-3131.
2. Cheer SM and Goa KL (2001) Fluoxetine: a review of its therapeutic potential in the treatment of depression associated with physical illness. Drugs 61:81-110.
3. Chen Z, Venkatesan AM, Dos Santos O, Delos Santos E, Dehnhardt CM, Ayral-Kaloustian S, Ashcroft J, McDonald LA, and Mansour TS (2010) Stereoselective synthesis of an active metabolite of the potent PI3 kinase inhibitor PKI-179. J Org Chem 75:1643-1651.
4. Dear GJ, Roberts AD, Beaumont C, and North SE (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 Analyt Technol Biomed Life Sci 876:182-190.
5. 19F NMR studies in animal models and human urine. Drug Metab Dispos 30:1221-12229.
6. Diehl BWK, Malz F, and Holzgrabe U (2007) Quantitative NMR spectroscopy in the quality evaluation of active pharmaceutical ingredients and excipients. Spec Eur 19:15-19.
7. 19F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR. Xenobiotica 36:59-77.
8. Espina R, Yu L, Wang J, Tong Z, Vashishtha S, Talaat R, Scatina J, and Mutlib A (2009) Nuclear magnetic resonance 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.
9. Evilia RF (2001) Quantitative NMR spectroscopy. Anal Lett 34:2227-2236.
10. Gibaldi M and Perrier D (1975) Pharmacokinetics, New York, Marcel Dekker.
11. Golightly LK and Greos LS (2005) Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs 65:341-384.
12. Groen D, Metternich HJ, and Schoenfelder W (1998) Quantitative NMR-spectroscopic analysis of the compounds of glycerol esters of fatty acids. Lipid 100:64-69.
13. Hays PA (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.
14. Holzgrabe U, Deubner R, Schollmayer C, and Waibel B (2005) Quantitative NMR spectroscopy - applications in drug analysis. J Pharm Biomed Anal 38:806-812. (Pubitemid 41115786)
15. Lennernäs H (2003) Clinical pharmacokinetics of atorvastatin. Clin Pharmacokinet 42:1141-1160.
16. Lenz EM, Wilson ID, Wright B, Partridge EA, Rodgers CT, Haycock PR, Lindon JC, and Nicholson JK (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.
17. Mackenzie IS (1984) Theoretical aspects of quantitative NMR. Anal Proc 21:500-502.
18. 19F nuclear magnetic resonance spectrometry. Cancer Res 46:2105-2112.
19. Malz F and Jancke H (2005) Validation of quantitative NMR. J Pharm Biomed Anal 38:813-823.
20. Malz F and Jancke H (2006) Purity assessment problem in quantitative NMR-impurity resonance overlaps with monitor signal multiplets from stereoisomers. Anal Bioanal Chem 385:760-765.
21. Meeves SG and Appajosyula S (2003) Efficacy and safety profile of fexofenadine HCl: a unique therapeutic option in H1-receptor antagonist treatment. J Allergy Clin Immunol 112:S69-S77.
22. Moazzami AA, Andersson RE, and Kamal-Eldin A (2007) Quantitative NMR analysis of a sesamin catechol metabolite in human urine. J Nutr 137:940-944.
23. 19F nuclear magnetic resonance spectroscopy of urine samples. J Pharm Biomed Anal 12:1489-1493.
24. Mutlib AE and Nelson WL (1990) Pathways of gallopamil metabolism. Regiochemistry and enantioselectivity of the N-dealkylation processes. Drug Metab Dispos 18:331-337.
25. Mutlib AE and Shockcor JP (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 JS, Obach RS, and Fisher MB eds) pp 33-86, Fontis Media, New York.
26. 19F-nuclear magnetic resonance and gas chromatography-electron capture detection in the quantitative analysis of fluorine-containing metabolites in urine of sevoflurane-anaesthetized patients. Xenobiotica 34:301-316.
27. Pauli GF, Jaki BU, and Lankin DC (2005) Quantitative 1H NMR: development and potential of a method for natural products analysis. J Nat Prod 68:133-149.
28. Pauli GF, Jaki BU, and Lankin DC (2007) A routine experimental protocol for qHNMR illustrated with Taxol. J Nat Prod 70:589-595.
29. Pauli GF, Jaki BU, Lankin DC, and Walter JA (2008) Quantitative NMR of bioactive natural products, in Bioactive Natural Products: Detection, Isolation and Structural Determination (Colgate SM and Molyneux RJ eds) pp 113-141, CRC Press, Boca Raton, FL.
30. Prestegard JH (2002) High resolution NMR of biomolecules. Lecture Notes Phys 595:426-434.
31. Rizzo V and Pinciroli V (2005) Quantitative NMR in synthetic and combinatorial chemistry. J Pharm Biomed Anal 38:851-857.
32. 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.
33. 19F-NMR spectroscopy and directly coupled HPLC-NMR-MS. Xenobiotica 29:77-91.
34. Shao G, Kautz R, Peng S, Cui G, and Giese RW (2007) Calibration by NMR for quantitative analysis: p-toluenesulfonic acid as a reference substance. J Chromatogr A 1138:305-308.
35. 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism. Xenobiotica 34:1075-1089.
36. 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.
37. U.S. Food and Drug Administration (2008) Guidance for industry: safety testing of drug metabolites. U.S. Food and Drug Administration, Center for Drug Evaluation and Research, Washington, DC.
38. Venkatesan AM, Dehnhardt CM, Delos Santos E, Chen Z, Dos Santos O, Ayral-Kaloustian S, Khafizova G, Brooijmans N, Mallon R, Hollander I, et al. (2010) Bis(morpholino-1,3,5- triazine) derivatives: potent adenosine 5′-triphosphate competitive phosphatidylinositol-3- kinase/mammalian target of rapamycin inhibitors: discovery of compound 26 (PKI-587), a highly efficacious dual inhibitor. J Med Chem 53:2636-2645.
39. Vinson JA and Kozak DM (1978) Analysis of aspirin tablets using quantitative NMR. Am J Pharm Educ 42:290-291.
40. Vishwanathan K, Babalola K, Wang J, Espina R, Yu L, Adedoyin A, Talaat R, Mutlib A, and Scatina J (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.
41. Warren RJ, Zarembo JE, Staiger DB, and Post A (1976) Quantitative NMR analysis of a four-component mixture of phenylglycine derivatives. J Pharm Sci 65:738-740.
42. Werner I, Bacher A, and Eisenreich W (1997) Retrobiosynthetic NMR studies with 13C-labeled glucose. Formation of gallic acid in plants and fungi. J Biol Chem 272:25474-25482.
43. Williams D and Feely J (2002) Pharmacokinetic-pharmacodynamic drug interactions with HMG-CoA reductase inhibitors. Clin Pharmacokinet 41: 343-370.