Studies of urinary metabolites of 2-(4-isobutylphenyl)propionic acid by gas-liquid chromatography-mass spectrometry

Brooks, C. J. W.; Gilbert, Mary T.

doi:10.1016/s0021-9673(00)90883-5

Cited by 47 publications

(5 citation statements)

References 12 publications

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“…When the urine sample was analyzed using the enantioselective OV1701-DMPen column and SRM, residual IB showed a high enantiomeric excess of ( S )-IB ( S/R = 95:5; ER = 19, see chromatogram in Figure b), although the racemic compound was used as the drug. This finding is in accordance with previous data obtained using various other analytical techniques (diastereomeric derivative formation; high-performance liquid chromatography) ( − ). The urine, when analyzed by full-scan MS using the DB-5 column, showed a complex pattern of components, among which the methyl esters of IB, hydroxy-IB, carboxy-IB (major), and carboxy-HA (minor) were clearly observed (see chromatogram in Figure a).…”

Section: Resultssupporting

confidence: 93%

Occurrence and Environmental Behavior of the Chiral Pharmaceutical Drug Ibuprofen in Surface Waters and in Wastewater

Buser¹,

Poiger²,

Müller³

1999

Environ. Sci. Technol.

604

320

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Pharmaceutical compounds can reach detectable concentrations in rivers and lakes if production and use are sufficiently large and the compounds show some mobility and persistence in the aquatic environment. In this study, we report on the occurrence and on the enantiomer composition of the chiral pharmaceutical drug ibuprofen (IB) in surface waters and in samples from wastewater treatment plants (WWTPs). Enantioselective gas chromatography and detection by mass spectrometry/mass spectrometry was used for analysis. IB was present in influents of WWTPs at concentrations of up to 3 µg/L with a high enantiomeric excess of the pharmacologically active S enantiomer (S . R), as from human urinary excretion. The principal human urinary metabolites of IB, hydroxy-IB and carboxy-IB, were observed in WWTP influents at even higher concentrations. In contrast to other pharmaceutical compounds such as clofibric acid and diclofenac, IB and its metabolites are then efficiently degraded (>95%) during treatment in WWTPs. Laboratory incubation experiments confirmed this rapid degradation. In rivers and lakes, IB was detected at concentrations of up to 8 ng/L, generally with some excess of the S enantiomer; the IB metabolites were not detected (<1 ng/L). Incubation of lake water fortified with (rac)-IB indicated a faster dissipation of the S enantiomer, thus resulting eventually in residues with a reversed (R > S) enantiomer composition as compared to that from human metabolism. Inefficient WWTPs and direct discharges of untreated wastewater from storm events, however, can still be a source for increased levels of IB in surface water.

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Section: Resultssupporting

confidence: 93%

Occurrence and Environmental Behavior of the Chiral Pharmaceutical Drug Ibuprofen in Surface Waters and in Wastewater

Buser¹,

Poiger²,

Müller³

1999

Environ. Sci. Technol.

604

320

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“…These results are in agreement with studies of the metabolism of 2-(4-isobutylphenyl)-propionic acid (Ibuprofen), where side chain oxidation products analogous to MI, M2 and M3 were demonstrated (8)(9)(10).…”

Section: Discussionsupporting

confidence: 91%

Metabolism of isobutylnaphthyl acetic acid in rats: determination of the chemical structures of metabolites

Achtert¹,

Borchers²,

Jacquot

et al. 1989

Eur. J. Drug Metab. Pharmacokinet.

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After oral and intravenous administration of radiolabelled isobutylnaphthyl acetic acid (INAA) to rats two metabolites were isolated from urine and plasma by HPLC. Field desorption, high resolution electron impact mass spectrometry as well as GC-MS after derivatization were used for structure elucidation and identification of the metabolites. The main biotransformation product in rat urine was found to be 5-(2'-hydroxy-2'-methyl-propyl)-1-naphthyl acetic acid (M1). The main metabolite in plasma was derived and was found to be 5-(2'-carboxypropyl)-1-naphthyl acetic acid (M2).

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“…We then examined the samples for evidence of ibuprofen metabolites using the combination of low (5 eV) and high (25 eV) collision energies to generate both molecular ion and fragment ion data. Given that hydroxylation and subsequent glucuronidation are well‐established metabolic fates for ibuprofen in humans,14, 15 resulting in an increase in molecular mass to ca. 397 Da, the sample was therefore examined for the presence of this type of metabolite.…”

Section: Resultsmentioning

confidence: 99%

High‐temperature ultra‐performance liquid chromatography coupled to hybrid quadrupole time‐of‐flight mass spectrometry applied to ibuprofen metabolites in human urine

Plumb

Rainville

Potts

et al. 2007

Rapid Comm Mass Spectrometry

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The application of sub-2 microm porous particle liquid chromatography (LC) operated at elevated temperatures, coupled with time-of-flight mass spectrometry (MS), to the separation and identification of metabolites of ibuprofen present in human urine following oral administrations is illustrated. The LC/MS system generated a high-resolution analytical separation that, with an analysis time of 20 min, provided a peak capacity in the order of ca. 350. Using this system a total of nine glucuronides of the drug and its metabolites were detected, including a number of isomeric acyl glucuronides of ibuprofen itself, a side-chain-oxidized carboxylic acid acyl glucuronide and a number of acyl glucuronides of various hydroxylated metabolites. The identities of the metabolites were confirmed by their accurate mass values and the presence of the common fragment ions from ibuprofen.

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Studies of urinary metabolites of 2-(4-isobutylphenyl)propionic acid by gas-liquid chromatography-mass spectrometry

Cited by 47 publications

References 12 publications

Occurrence and Environmental Behavior of the Chiral Pharmaceutical Drug Ibuprofen in Surface Waters and in Wastewater

Occurrence and Environmental Behavior of the Chiral Pharmaceutical Drug Ibuprofen in Surface Waters and in Wastewater

Metabolism of isobutylnaphthyl acetic acid in rats: determination of the chemical structures of metabolites

High‐temperature ultra‐performance liquid chromatography coupled to hybrid quadrupole time‐of‐flight mass spectrometry applied to ibuprofen metabolites in human urine

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