Imperial College London

Emeritus ProfessorJeremyNicholson

Faculty of MedicineDepartment of Metabolism, Digestion and Reproduction

Emeritus Professor of Biological Chemistry



+44 (0)20 7594 3195j.nicholson Website




Ms Wendy Torto +44 (0)20 7594 3225




Office no. 665Sir Alexander Fleming BuildingSouth Kensington Campus






BibTex format

author = {Bollard, ME and Holmes, E and Blackledge, CA and Lindon, JC and Wilson, ID and Nicholson, JK},
doi = {10.3109/00498259609046706},
journal = {Xenobiotica},
pages = {255--273},
title = {<sup>1</sup>H and <sup>19</sup>F-nmr spectroscopic studies on the metabolism and urinary excretion of mono- and disubstituted phenols in the rat},
url = {},
volume = {26},
year = {1996}

RIS format (EndNote, RefMan)

AB - 1. 1H and 19F-nmr spectroscopy was used to investigate quantitatively the urinary excretion of the metabolites of 15 substituted phenols in the rat. The compounds studied were: 2-, 3-, and 4-fluorophenols; 2-, 3-, and 4-trifluoromethylphenol; 2,4-, 2,6- and 3,4-difluorophenol; 2-fluoro-5-trifluoromethylphenol, 3-fluoro-5-trifluoromethylphenol, 2-trifluoromethyl-4-fluorophenol; 3-chloro-4-fluorophenol, 3-fluoro-4-chlorophenol, and 3-methyl-4-fluorophenol. All compounds were dosed to the Sprague-Dawley rat (10 mg/kg i.p.) and urine was collected over the periods 0-8, 8-24 and 24-48 h post-dosing and analyzed using nmr spectroscopy. 2. The compounds were excreted in the urine mainly as glucuronide or sulphate conjugates or as the unchanged parent compound. There was considerable variation in the urinary excretion of the compounds over 48 h ranging from 22·1 to 93·6% of the dose. There was no apparent relationship between the molecular weight of compounds or their metabolites and the percentage molar recovery of each in the urine. 3. Ortho-substituted phenols in general showed a greater propensity for glucuronidation than did either meta- or para-substituted compounds, irrespective of the substituent group. The molar glucuronide-to-sulphate ratio for ortho-substituted compounds was found to be 2·2 ± 0·9 whereas the ratio for both meta- and para-substituted compounds was 0·8 ± 0·2 (p < 0·0001). 4. There were characteristic substituent effects of phenolic glucuronidation or sulphation on the 19F-nmr chemical shifts for both F- and CF3-substituted phemols and these substituent effects were a useful aid to metabolite signal assignment. 5. These studies show that nmr spectroscopy provides a rapid and convenient approach to the construction of metabolic databases of simple xenobiotics for the investigation of structure-metabolism relationships.
AU - Bollard,ME
AU - Holmes,E
AU - Blackledge,CA
AU - Lindon,JC
AU - Wilson,ID
AU - Nicholson,JK
DO - 10.3109/00498259609046706
EP - 273
PY - 1996///
SN - 0049-8254
SP - 255
TI - <sup>1</sup>H and <sup>19</sup>F-nmr spectroscopic studies on the metabolism and urinary excretion of mono- and disubstituted phenols in the rat
T2 - Xenobiotica
UR -
VL - 26
ER -