Advanced search
Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 28, 1998 - Issue 4
Submit an article Journal homepage
73
Views
48
CrossRef citations to date
0
Altmetric
Research Article

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

G. B. SCARFE Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
,
B. WRIGHT Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
,
E. CLAYTON Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
,
S. TAYLOR Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
,
I. D. WILSON Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
,
J. C. LINDON Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
&
J. K. NICHOLSON Department of Chemistry, Birkbeck College, University of London, Gordon House, 29 Gordon Square, London WC1H 0PP, UK OE Department of Safety of Medicines, Zeneca Pharmaceuticals, Mereside, Alderley Park, Maccleseld SK10 4TG, UK
 show all
Pages 373-388 | Published online: 22 Sep 2008

Citations (48)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (8)

David Pearson, Maxime Garnier, Alexandre Luneau, Alexander David James & Markus Walles. (2019) 19F-NMR-based determination of the absorption, metabolism and excretion of the oral phosphatidylinositol-3-kinase (PI3K) delta inhibitor leniolisib (CDZ173) in healthy volunteers. Xenobiotica 49:8, pages 953-960.
Read now
Toby J. Athersuch, Ian D. Wilson, Hector C. Keun & John C. Lindon. (2013) Development of quantitative structure-metabolism (QSMR) relationships for substituted anilines based on computational chemistry. Xenobiotica 43:9, pages 792-802.
Read now
T. J. Athersuch, J. Castro-Perez, C. Rodgers, J. K. Nicholson & I. D. Wilson. (2010) UPLC-MS, HPLC-radiometric, and NMR-spectroscopic studies on the metabolic fate of 3-fluoro-[U-14C]-aniline in the bile-cannulated rat. Xenobiotica 40:7, pages 510-523.
Read now
J. G. Bundy, E. M. Lenz, D. Osborn, J. M. Weeks, J. C. Lindon & J. K. Nicholson. (2002) Metabolism of 4-fluoroaniline and 4-fluorobiphenyl in the earthworm Eisenia veneta characterized by high-resolution NMR spectroscopy with directly coupled HPLC-NMR and HPLC-MS. Xenobiotica 32:6, pages 479-490.
Read now
G. B. Scarfe, I. D. Wilson, M. A. Warne, E. Holmes, J. K. Nicholson & J. C. Lindon. (2002) Structure-metabolism relationships of substituted anilines: prediction of N-acetylation and N-oxanilic acid formation using computational chemistry. Xenobiotica 32:4, pages 267-277.
Read now
I. M. Ismail, G. J. Dear, A. D. Roberts, R. S. Plumb, J. Ayrton, B. C. Sweatman & G. D. Bowers. (2002) N-O glucuronidation: a major human metabolic pathway in the elimination of two novel anticonvulsant drug candidates. Xenobiotica 32:1, pages 29-43.
Read now
G. B. SCARFE. (1999) Quantitative studies on the urinary metabolic fate of 2-chloro-4-trifluoromethylaniline in the rat using 19F-NMR spectroscopy and directly coupled HPLCNMR-MS. Xenobiotica 29:1, pages 77-91.
Read now
G. B. SCARFE. (1999) Studies on the metabolism of 4-fluoroaniline and 4-fluoroacetanilide in rat: formation of 4-acetamidophenol (paracetamol) and its metabolites via defluorination and N-acetylation. Xenobiotica 29:2, pages 205-216.
Read now

Articles from other publishers (40)

Sahar Baig, Kamala Vanarsa, Huihua Ding, Anto Sam Crosslee Louis Sam Titus, Maureen McMahon & Chandra Mohan. (2022) Baseline Elevations of Leukotriene Metabolites and Altered Plasmalogens Are Prognostic Biomarkers of Plaque Progression in Systemic Lupus Erythematosus. Frontiers in Cardiovascular Medicine 9.
Crossref
Marine P. M. Letertre, Patrick Giraudeau & Pascal de Tullio. (2021) Nuclear Magnetic Resonance Spectroscopy in Clinical Metabolomics and Personalized Medicine: Current Challenges and Perspectives. Frontiers in Molecular Biosciences 8.
Crossref
Dipali Sonawane, Anuradha Reddy, Tarang Jadav, Amit K Sahu, Rakesh K Tekade & Pinaki Sengupta. (2021) Advancements in practical and scientific bioanalytical approaches to metabolism studies in drug development. Bioanalysis 13:11, pages 913-930.
Crossref
. 2020. ANSI/AAMI/ISO 10993-16:2017; Biological evaluation of medical devices—Part 16: Toxicokinetic study design for degradation products and leachables. ANSI/AAMI/ISO 10993-16:2017; Biological evaluation of medical devices—Part 16: Toxicokinetic study design for degradation products and leachables.
Eleonora Candi, Manfredi Tesauro, Carmine Cardillo, Anna Maria Lena, Francesca Schinzari, Giuseppe Rodia, Giuseppe Sica, Paolo Gentileschi, Valentina Rovella, Margherita Annicchiarico-Petruzzelli, Nicola Di Daniele & Gerry Melino. (2018) Metabolic profiling of visceral adipose tissue from obese subjects with or without metabolic syndrome. Biochemical Journal 475:5, pages 1019-1035.
Crossref
Gabriele Sabbioni. (2017) Hemoglobin Adducts and Urinary Metabolites of Arylamines and Nitroarenes. Chemical Research in Toxicology 30:10, pages 1733-1766.
Crossref
Alexander David James, Cyrille Marvalin, Alexandre Luneau, Axel Meissner & Gian Camenisch. (2017) Comparison of 19 F NMR and 14 C Measurements for the Assessment of ADME of BYL719 (Alpelisib) in Humans . Drug Metabolism and Disposition 45:8, pages 900-907.
Crossref
Seokjae Park, Krishna Chaitanya Sadanala & Eun-Kyoung Kim. (2015) A Metabolomic Approach to Understanding the Metabolic Link between Obesity and Diabetes. Molecules and Cells 38:7, pages 587-596.
Crossref
John C. Lindon & Ian D. Wilson. 2007. eMagRes. eMagRes 189 196 .
Abdul E. Mutlib. 2014. Handbook of Metabolic Pathways of Xenobiotics. Handbook of Metabolic Pathways of Xenobiotics 1 31 .
Fuyong Du, Anthony Virtue, Hong Wang & Xiao-Feng Yang. (2013) Metabolomic analyses for atherosclerosis, diabetes, and obesity. Biomarker Research 1:1.
Crossref
Abdul Mutlib, Robert Espina, James Atherton, Jianyao Wang, Rasmy Talaat, JoAnn Scatina & Appavu Chandrasekaran. (2012) Alternate Strategies to Obtain Mass Balance without the Use of Radiolabeled Compounds: Application of Quantitative Fluorine ( 19 F) Nuclear Magnetic Resonance (NMR) Spectroscopy in Metabolism Studies . Chemical Research in Toxicology 25:3, pages 572-583.
Crossref
Maria Victoria Silva Elipe. 2011. LC-NMR and Other Hyphenated NMR Techniques. LC-NMR and Other Hyphenated NMR Techniques 131 142 .
Maria Victoria Silva Elipe. 2011. LC-NMR and Other Hyphenated NMR Techniques. LC-NMR and Other Hyphenated NMR Techniques 39 57 .
Abdul Mutlib, Robert Espina, Karthick Vishwanathan, Kathlene Babalola, Zecheng Chen, Christoph Dehnhardt, Aranapakam Venkatesan, Tarek Mansour, Inder Chaudhary, Rasmy Talaat & JoAnn Scatina. (2011) Application of Quantitative NMR in Pharmacological Evaluation of Biologically Generated Metabolites: Implications in Drug Discovery. Drug Metabolism and Disposition 39:1, pages 106-116.
Crossref
I.D. Wilson. 2008. NMR Spectroscopy in Pharmaceutical Analysis. NMR Spectroscopy in Pharmaceutical Analysis 449 469 .
Ian D. Wilson & Udo A.Th. Brinkman. (2007) Hype and hypernation: multiple hyphenation of column liquid chromatography and spectroscopy. TrAC Trends in Analytical Chemistry 26:9, pages 847-854.
Crossref
Toby J. Athersuch, Jeremy K. Nicholson & Ian D. Wilson. (2007) Isotopic enrichment enhancement in metabonomic analysis of UPLC–MS data sets. Journal of Labelled Compounds and Radiopharmaceuticals 50:5-6, pages 303-307.
Crossref
Graham Lappin. 2006. Radiotracers in Drug Development. Radiotracers in Drug Development 41 118 .
Graham Lappin. 2006. Radiotracers in Drug Development. Radiotracers in Drug Development 1 15 .
Zheng Yang. (2006) Online hyphenated liquid chromatography–nuclear magnetic resonance spectroscopy–mass spectrometry for drug metabolite and nature product analysis. Journal of Pharmaceutical and Biomedical Analysis 40:3, pages 516-527.
Crossref
Ian D. Wilson. 2004. Chromatography 6th Edition - Fundamentals and Applications of Chromatography and Related Differential Migration Methods. Chromatography 6th Edition - Fundamentals and Applications of Chromatography and Related Differential Migration Methods 945 985 .
Maria Victoria Silva Elipe. (2003) Advantages and disadvantages of nuclear magnetic resonance spectroscopy as a hyphenated technique. Analytica Chimica Acta 497:1-2, pages 1-25.
Crossref
J. Fred Pritchard, Malle Jurima-Romet, Mark L. J. Reimer, Elisabeth Mortimer, Brenda Rolfe & Mitchell N. Cayen. (2003) Making Better Drugs: Decision Gates in Non-Clinical Drug Development. Nature Reviews Drug Discovery 2:7, pages 542-553.
Crossref
E.M. Lenz, J.C. Lindon, J.K. Nicholson, J.M. Weeks & D. Osborn. (2003) 19F NMR spectroscopic investigation into the absorption and metabolism of 3-trifluoromethylaniline in Eisenia veneta. Ecotoxicology and Environmental Safety 54:2, pages 157-168.
Crossref
John C. Lindon, Nigel J.C. Bailey, Jeremy K. Nicholson & Ian D. Wilson. 2003. Bioanalytical Separations. Bioanalytical Separations 293 329 .
M Tugnait, E.M Lenz, M Hofmann, M Spraul, I.D Wilson, J.C Lindon & J.K Nicholson. (2003) The metabolism of 2-trifluormethylaniline and its acetanilide in the rat by 19F NMR monitored enzyme hydrolysis and 1H/19F HPLC-NMR spectroscopy. Journal of Pharmaceutical and Biomedical Analysis 30:5, pages 1561-1574.
Crossref
Dave Louden, Alan Handley, Rene Lafont, Steve Taylor, Ian Sinclair, Eva Lenz, Timothy Orton & Ian D. Wilson. (2001) HPLC Analysis of Ecdysteroids in Plant Extracts Using Superheated Deuterium Oxide with Multiple On-Line Spectroscopic Analysis (UV, IR, 1 H NMR, and MS) . Analytical Chemistry 74:1, pages 288-294.
Crossref
Eva Lenz, Steve Taylor, Craig Collins, Ian D Wilson, Dave Louden & Alan Handley. (2002) Flow injection analysis with multiple on-line spectroscopic analysis (UV, IR, 1H-NMR and MS). Journal of Pharmaceutical and Biomedical Analysis 27:1-2, pages 191-200.
Crossref
Jeremy K. Nicholson, John C. Lindon, Graeme B. Scarfe, Ian D. WilsonFadi Abou-Shakra, Ashley B. Sage & Jose Castro-Perez. (2001) High-Performance Liquid Chromatography Linked to Inductively Coupled Plasma Mass Spectrometry and Orthogonal Acceleration Time-of-Flight Mass Spectrometry for the Simultaneous Detection and Identification of Metabolites of 2-Bromo-4- trifluoromethyl-[ 13 C]-acetanilide in Rat Urine . Analytical Chemistry 73:7, pages 1491-1494.
Crossref
Dave Louden, Alan Handley, Steve Taylor, Eva Lenz, Steve Miller, Ian D Wilson, Ashley Sage & R Lafont. (2001) Spectroscopic characterisation and identification of ecdysteroids using high-performance liquid chromatography combined with on-line UV–diode array, FT-infrared and 1H-nuclear magnetic resonance spectroscopy and time of flight mass spectrometry. Journal of Chromatography A 910:2, pages 237-246.
Crossref
Graeme B. Scarfe, Edward Clayton, Ian D. Wilson & Jeremy K. Nicholson. (2000) Identification and quantification of metabolites of 2,3,5,6-tetrafluoro-4-trifluoromethylaniline in rat urine using 19F nuclear magnetic resonance spectroscopy, high-performance liquid chromatography–nuclear magnetic resonance spectroscopy and high-performance liquid chromatography–mass spectrometry. Journal of Chromatography B: Biomedical Sciences and Applications 748:1, pages 311-319.
Crossref
John C Lindon, Jeremy K Nicholson & Ian D Wilson. (2000) Directly coupled HPLC–NMR and HPLC–NMR–MS in pharmaceutical research and development. Journal of Chromatography B: Biomedical Sciences and Applications 748:1, pages 233-258.
Crossref
I.D Wilson. (2000) Multiple hyphenation of liquid chromatography with nuclear magnetic resonance spectroscopy, mass spectrometry and beyond. Journal of Chromatography A 892:1-2, pages 315-327.
Crossref
Dave Louden, Alan Handley, Steve Taylor, Eva Lenz, Steve Miller, Ian D. Wilson & Ashley Sage. (2000) Reversed-Phase High-Performance Liquid Chromatography Combined with On-Line UV Diode Array, FT Infrared, and 1 H Nuclear Magnetic Resonance Spectroscopy and Time-of-Flight Mass Spectrometry:  Application to a Mixture of Nonsteroidal Antiinflammatory Drugs . Analytical Chemistry 72:16, pages 3922-3926.
Crossref
A. Lommen, M. Godejohann, D. P. Venema, P. C. H. Hollman & M. Spraul. (2000) Application of Directly Coupled HPLC−NMR−MS to the Identification and Confirmation of Quercetin Glycosides and Phloretin Glycosides in Apple Peel. Analytical Chemistry 72:8, pages 1793-1797.
Crossref
Roger M. Smith, Orapin Chienthavorn, Ian D. Wilson, Brian Wright & Stephen D. Taylor. (1999) Superheated Heavy Water as the Eluent for HPLC-NMR and HPLC-NMR-MS of Model Drugs. Analytical Chemistry 71:20, pages 4493-4497.
Crossref
Mike Ludlow, Dave Louden, Alan Handley, Steve Taylor, Brian Wright & Ian D Wilson. (1999) Size-exclusion chromatography with on-line ultraviolet, proton nuclear magnetic resonance and mass spectrometric detection and on-line collection for off-line Fourier transform infrared spectroscopy. Journal of Chromatography A 857:1-2, pages 89-96.
Crossref
Ray Bakhtiar & Cornelis E. C. A. Hop. (1999) Unravelling seemingly complex chemistry of reactions using electrospray ionization mass spectrometry. Journal of Physical Organic Chemistry 12:7, pages 511-527.
Crossref
John C. Lindon, Jeremy K. Nicholson & Jeremy R. Everett. 1999. Annual Reports on NMR Spectroscopy Volume 38. Annual Reports on NMR Spectroscopy Volume 38 1 88 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.