Applications of LC-MS to quantitation and evaluation of the environmental fate of chiral drugs and their metabolites

This review provides a brief overview on chirality as a structural characteristic of pharmaceuticals. This property has received very little attention in the field of environmental analysis, despite the fact that many drugs are marketed as racemates. The review covers the different methodologies commercially available on chiral liquid chromatography (LC) columns to provide good resolving power. It also reviews recent results obtained in chiral analysis of drugs and their metabolites with an array of modern mass-spectrometric analyzers coupled to an LC system that provides high selectivity and sensitivity. It further covers the occurrence and the fate of chiral drugs in the environment.

[1]  H. Kanazawa,et al.  Determination of omeprazole and its metabolites in human plasma by liquid chromatography-mass spectrometry. , 2002, Journal of chromatography. A.

[2]  A. Somogyi,et al.  Stereoselective quantification of methadone and its major oxidative metabolite, 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, in human urine using high-performance liquid chromatography. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[3]  D. Epstein,et al.  Determination of total and free concentrations of the enantiomers of methadone and its metabolite (2-ethylidene-1,5-dimethyl-3,3-diphenyl-pyrrolidine) in human plasma by enantioselective liquid chromatography with mass spectrometric detection. , 2005, Journal of chromatography. A.

[4]  K. Wommack,et al.  Influence of environmental changes on degradation of chiral pollutants in soils , 1999, Nature.

[5]  A. Ohnishi,et al.  Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. , 2001, Journal of chromatography. A.

[6]  J. Hermansson,et al.  Optimization of the separation of enantiomers of basic drugs. Retention mechanisms and dynamic modification of the chiral bonding properties on an alpha 1-acid glycoprotein column. , 1995, Journal of chromatography. A.

[7]  S. Laufer,et al.  Stereospecific pharmacokinetic characterisation of phenprocoumon metabolites, and mass-spectrometric identification of two novel metabolites in human plasma and liver microsomes , 2005, Analytical and bioanalytical chemistry.

[8]  Walter A. Korfmacher,et al.  Chiral liquid chromatography-tandem mass spectrometric methods for stereoisomeric pharmaceutical determinations. , 2005, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[9]  Charles S Wong,et al.  Environmental fate processes and biochemical transformations of chiral emerging organic pollutants , 2006, Analytical and bioanalytical chemistry.

[10]  D. Siluk,et al.  Simultaneous determination of buprenorphine, norbuprenorphine and the enantiomers of methadone and its metabolite (EDDP) in human plasma by liquid chromatography/mass spectrometry. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[11]  S. Ng,et al.  Effect of mobile phase composition on the separation of propranolol enantiomers using a perphenylcarbamate beta-cyclodextrin bonded chiral stationary phase. , 2000, Journal of chromatography. A.

[12]  P. S. Bonato,et al.  Enantioselective analysis of mirtazapine and its two major metabolites in human plasma by liquid chromatography-mass spectrometry after three-phase liquid-phase microextraction. , 2008, Analytica chimica acta.

[13]  D. Zhong,et al.  Enantioselective determination of propafenone and its metabolites in human plasma by liquid chromatography-mass spectrometry. , 1999, Journal of Chromatography B: Biomedical Sciences and Applications.

[14]  J. Roeraade,et al.  Evaluation of generic chiral liquid chromatography screens for pharmaceutical analysis. , 2003, Journal of chromatography. A.

[15]  Y. Heyden,et al.  Screening approach for chiral separation of pharmaceuticals IV. Polar organic solvent chromatography. , 2006, Journal of chromatography. A.

[16]  M. Chlenov,et al.  Normal-phase chiral liquid chromatography-mass spectrometry of non-UV-active compounds: applications for pharmaceutically relevant racemates. , 2006, Journal of chromatography. A.

[17]  H. Kohler,et al.  Chirality of pollutants—effects on metabolism and fate , 2004, Applied Microbiology and Biotechnology.

[18]  A. Cifuentes,et al.  Liquid separation techniques coupled with mass spectrometry for chiral analysis of pharmaceuticals compounds and their metabolites in biological fluids. , 2006, Journal of pharmaceutical and biomedical analysis.

[19]  A. Ceccato,et al.  Enantiomeric determination of tramadol and its main metabolite O-desmethyltramadol in human plasma by liquid chromatography-tandem mass spectrometry. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[20]  Hong Lu Stereoselectivity in drug metabolism , 2007, Expert opinion on drug metabolism & toxicology.

[21]  Edward P. Kolodziej,et al.  Attenuation of wastewater-derived contaminants in an effluent-dominated river. , 2006, Environmental science & technology.

[22]  T. Poiger,et al.  Occurrence and Environmental Behavior of the Chiral Pharmaceutical Drug Ibuprofen in Surface Waters and in Wastewater , 1999 .

[23]  Charles S Wong,et al.  Stereoisomer analysis of wastewater-derived beta-blockers, selective serotonin re-uptake inhibitors, and salbutamol by high-performance liquid chromatography-tandem mass spectrometry. , 2007, Journal of chromatography. A.

[24]  C. Walko,et al.  Enantioselective liquid chromatography-mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma. , 2007, Journal of pharmaceutical and biomedical analysis.

[25]  T. A. Walker,et al.  Bupropion hydrochloride: the development of a chiral separation using an ovomucoid column. , 2001, Journal of chromatography. A.

[26]  D. Sedlak,et al.  Use of the chiral pharmaceutical propranolol to identify sewage discharges into surface waters. , 2005, Environmental science & technology.

[27]  T. Iga,et al.  Stereoselective high-performance liquid chromatographic determination of ketamine and its active metabolite, norketamine, in human plasma. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[28]  B. Matuszewski,et al.  Matrix effect in quantitative LC/MS/MS analyses of biological fluids: a method for determination of finasteride in human plasma at picogram per milliliter concentrations. , 1998, Analytical chemistry.

[29]  R. C. Williams,et al.  Retention Characteristics of Protein-Based Chiral HPLC Columns , 1993 .

[30]  P. Malfertheiner,et al.  Enantioselective quantification of omeprazole and its main metabolites in human serum by chiral HPLC-atmospheric pressure photoionization tandem mass spectrometry. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[31]  I. Wainer,et al.  Determination of the enantiomers of ketamine and norketamine in human plasma by enantioselective liquid chromatography-mass spectrometry. , 2003, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[32]  Adriana Rocha,et al.  Enantioselective analysis of citalopram and demethylcitalopram in human and rat plasma by chiral LC-MS/MS: application to pharmacokinetics. , 2007, Chirality.

[33]  K. Kristensen,et al.  Enantioselective high-performance liquid chromatographic method for the determination of methadone and its main metabolite in urine using an AGP and a C8 column coupled serially. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[34]  Charles S Wong,et al.  Stereoisomer quantification of the β-blocker drugs atenolol, metoprolol, and propranolol in wastewaters by chiral high-performance liquid chromatography–tandem mass spectrometry , 2006 .

[35]  E. Kharasch,et al.  Stereoselective analysis of bupropion and hydroxybupropion in human plasma and urine by LC/MS/MS. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[36]  P. Lagerström,et al.  Determination of the enantiomers of omeprazole in blood plasma by normal-phase liquid chromatography and detection by atmospheric pressure ionization tandem mass spectrometry. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[37]  P. S. Bonato,et al.  Chiral liquid chromatographic determination of mirtazapine in human plasma using two-phase liquid-phase microextraction for sample preparation , 2005 .

[38]  W. Lindner,et al.  Chiral recognition applications of molecularly imprinted polymers: a critical review , 2007, Analytical and bioanalytical chemistry.

[39]  J. Syage,et al.  Comparison of atmospheric pressure photoionization and atmospheric pressure chemical ionization for normal-phase LC/MS chiral analysis of pharmaceuticals. , 2007, Analytical chemistry.

[40]  E. Tesařová,et al.  Comparison of vancomycin-based stationary phases with different chiral selector coverage for enantioselective separation of selected drugs in high-performance liquid chromatography. , 2005, Journal of chromatography. A.

[41]  M. Kosel,et al.  Analysis of the enantiomers of citalopram and its demethylated metabolites using chiral liquid chromatography. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[42]  A. Garrison Probing the enantioselectivity of chiral pesticides. , 2006, Environmental science & technology.