carboxyibuprofen and hydroxyibuprofen

A liquid chromatography quadruple time-of-flight mass spectrometry (LC-QqTOF-MS/MS) method was developed for simultaneous quantitative analysis of ibuprofen (IBU), 1- and 2-hydroxyibuprofen (1-OH IBU and 2-OH IBU), and carboxyibuprofen (CBX IBU) while preserving the ability of the instrument to get precursor and product ion mass spectra of non-target compounds. The trigger was the precursor ions reaching 100 cps intensity. Sample preparation was carried out by ultrasound solid-liquid extraction with methanol as extraction solvent at pH < 2 followed by solid-phase extraction (SPE) clean-up using STRATA-X cartridges and methanol as an eluent. Linearity was obtained in the range 50-10,000 ng mL

Topics: Chromatography, High Pressure Liquid; Ibuprofen; Limit of Detection; Plant Roots; Plant Shoots; Seeds; Soil Pollutants; Solid Phase Extraction; Tandem Mass Spectrometry; Vigna

A novel assay for the simultaneous determination of ibuprofen (IBU) and its four probable metabolites, 1-hydroxyibuprofen (1-OH IBU), 2-hydroxyibuprofen (2-OH IBU), 3-hydroxyibuprofen (3-OH IBU) and carboxyibuprofen (CBX IBU) in equine urine samples with the application of Gas Chromatography-Electron Ionization-Mass Spectrometry (GC-EI-MS) has been developed and elaborated. The new approach for sample preparation including minimizing matrix effects by the application of weak cation exchange solid-phase extraction together with strong cation exchange solid-phase extraction has been applied. The GC-EI-MS method was validated to demonstrate specificity, matrix effect, linearity, limit of detection (LOD) and quantification (LOQ), precision, trueness, carry-over and stability by using the matrix-matched quality control samples. Additionally, extraction yield was evaluated. The assay achieved the LOQ of 1.75 μg mL

Topics: Animals; Doping in Sports; Gas Chromatography-Mass Spectrometry; Horses; Ibuprofen; Limit of Detection; Solid Phase Extraction

The purpose of this study was the development and validation of an LC-MS-MS method for simultaneous analysis of ibuprofen (IBP), 2-hydroxyibuprofen (2-OH-IBP) enantiomers, and carboxyibuprofen (COOH-IBP) stereoisomers in fungi culture medium, to investigate the ability of some endophytic fungi to biotransform the chiral drug IBP into its metabolites. Resolution of IBP and the stereoisomers of its main metabolites was achieved by use of a Chiralpak AS-H column (150 × 4.6 mm, 5 μm particle size), column temperature 8 °C, and the mobile phase hexane-isopropanol-trifluoroacetic acid (95: 5: 0.1, v/v) at a flow rate of 1.2 mL min(-1). Post-column infusion with 10 mmol L(-1) ammonium acetate in methanol at a flow rate of 0.3 mL min(-1) was performed to enhance MS detection (positive electrospray ionization). Liquid-liquid extraction was used for sample preparation with hexane-ethyl acetate (1:1, v/v) as extraction solvent. Linearity was obtained in the range 0.1-20 μg mL(-1) for IBP, 0.05-7.5 μg mL(-1) for each 2-OH-IBP enantiomer, and 0.025-5.0 μg mL(-1) for each COOH-IBP stereoisomer (r ≥ 0.99). The coefficients of variation and relative errors obtained in precision and accuracy studies (within-day and between-day) were below 15%. The stability studies showed that the samples were stable (p > 0.05) during freeze and thaw cycles, short-term exposure to room temperature, storage at -20 °C, and biotransformation conditions. Among the six fungi studied, only the strains Nigrospora sphaerica (SS67) and Chaetomium globosum (VR10) biotransformed IBP enantioselectively, with greater formation of the metabolite (+)-(S)-2-OH-IBP. Formation of the COOH-IBP stereoisomers, which involves hydroxylation at C3 and further oxidation to form the carboxyl group, was not observed.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Biotransformation; Chromatography, High Pressure Liquid; Fungi; Ibuprofen; Stereoisomerism; Tandem Mass Spectrometry

Horizontal subsurface flow constructed wetlands (SSFCWs) are a cost-effective and sustainable alternative to conventional wastewater treatment plants (WWTPs) for sanitation in small communities. SSFCWs are designed to remove suspended solids and organic matter from wastewater but there is little information on the effect of the characteristics of organic matter on the removal efficiency of specific contaminants. In this paper, carbamazepine, ibuprofen and clofibric acid were continuously injected into two SSFCW microcosms fed with synthetic wastewater containing different organic matter sources: dissolved (glucose) and particulate (starch). The response curves of carbamazepine and ibuprofen were compared with that of clofibric acid, which was used as a conservative tracer. The removal efficiencies were found to be independent of the organic matter type (i.e. dissolved or particulate). Carbamazepine was removed inefficiently (5%) by bed sorption, whereas ibuprofen was removed by degradation (51%). In addition, the behaviour of the two main ibuprofen biodegradation intermediates (carboxy and hydroxy derivatives) supported that the main ibuprofen elimination pathway occurs in aerobic conditions.

Topics: Biodegradation, Environmental; Carbamazepine; Clofibric Acid; Glucose; Ibuprofen; Poaceae; Quaternary Ammonium Compounds; Starch; Sulfates; Waste Disposal, Fluid; Water Pollutants, Chemical; Wetlands

Racemic ibuprofen is an important NSAID used in the treatment of pain and inflammation in a variety of musculoskeletal and rheumatic disorders. The metabolism of ibuprofen, and that of a number of the related 2-arylpropionic acid NSAIDs, involves chiral inversion of the relatively inactive R-enantiomers to their active S-antipodes, together with other potentially stereoselective conjugative and oxidative pathways. Enantiospecific analytical methodology suitable for the determination of both the drug and its metabolites is essential in order to evaluate the significance of stereoselectivity both in terms of drug action and disposition. Recent investigations have also indicated that the R-enantiomers of these agents may not be totally devoid of useful biological activity, that the formation of acyl-coenzyme A derivatives results in interactions with lipid biochemistry, and has provided new insights into the disposition of these drugs in man. Ibuprofen represents a classical example of a drug where stereochemical considerations are essential for an understanding of its biological properties.

Topics: Acyl Coenzyme A; Anti-Inflammatory Agents, Non-Steroidal; Chromatography, High Pressure Liquid; Cyclooxygenase Inhibitors; Ibuprofen; Molecular Conformation; Pharmacokinetics; Stereoisomerism

A capillary electrophoresis method for determination of the enantiomers of ibuprofen and its major phase I metabolites: 2'-hydroxyibuprofen and 2'-carboxyibuprofen in urine samples have been developed. Cyclodextrins and linear dextrins have been investigated as chiral selectors. Simultaneous chiral separation of the enantiomers of ibuprofen, 2'-hydroxyibuprofen and 2'-carboxyibuprofen was obtained using a mixture of dextrin 10 and heptakis (2,3,6-tri-O-methyl)-beta-cyclodextrin in a 2-[N-morpholino]ethanesulphonic acid buffer, pH 5.26. The electroosmotic flow was reversed using hexadimethrine bromide as a buffer additive. The method can be used for the determination of the free enantiomers of ibuprofen, 2'-hydroxyibuprofen and 2'-carboxyibuprofen as well as for the indirect determination of their glucuronic acid conjugates in urine samples.

Topics: beta-Cyclodextrins; Buffers; Cyclodextrins; Dextrins; Electrophoresis, Capillary; Glucuronates; Humans; Hydrogen-Ion Concentration; Ibuprofen; Indicators and Reagents; Stereoisomerism

A sequential achiral-chiral HPLC method has been developed for the stereospecific analysis of the two major urinary metabolites of ibuprofen, namely hydroxyibuprofen and carboxyibuprofen. Achiral analysis was carried out using a Partisil column (250x4.6 mm, 5 microm) and a mobile phase of hexane:ethanol (98.2:1.8, v/v) containing trifluoroacetic acid (TFA; 0.05%, v/v) at a flow-rate of 2.0 ml/min. The HPLC eluate containing the two metabolites was separately collected, evaporated under nitrogen and the residue dissolved in the mobile phase used for chiral chromatography. Chiral-phase analysis was carried out using a Chiralpak AD CSP (250x4.6 mm, 10 microm) with a mobile phase of hexane:ethanol (92:8, v/v) containing TFA (0.05%, v/v) at a flow-rate of 1.0 ml/min. In both assays the analytes were quantified by ultraviolet detection at a wavelength of 220 nm. Modification of the mobile-phase composition allowed the resolution of all six analytes in a single chromatographic run but with an increase in run time and consequent band broadening. The analytical method described allows the direct quantitation of the stereoisomers of both metabolites of ibuprofen in urine following the administration of therapeutic doses of the racemic drug to man.

Topics: Adult; Anti-Inflammatory Agents, Non-Steroidal; Chromatography, High Pressure Liquid; Female; Humans; Ibuprofen; Male; Reproducibility of Results; Stereoisomerism