Simultaneous chiral analytes of multiple analytes: Case studies, implications and method development considerations

Biomedical Chromatography

Volumn 18, Issue 10, 2004, Pages 759-784

  Srinivas, Nuggehally R ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Chiral derivatization agents; Chiral separations; Chiral stationary phases; Multiple chiral analytes; Review

Indexed keywords

BIOMOLECULES; CHIRALITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; PHARMACOKINETICS; STEREOSELECTIVITY;

CASE METHOD; CASE-STUDIES; CHIRAL ANALYTES; CHIRAL DERIVATIZATION AGENT; CHIRAL SEPARATIONS; CHIRAL STATIONARY PHASE; DERIVATIZATIONS; METHOD DEVELOPMENT; MULTIPLE ANALYTES; MULTIPLE CHIRAL ANALYTE;

ENANTIOMERS;

3,4 METHYLENEDIOXYMETHAMPHETAMINE; 4' HYDROXYMEPHENYTOIN; ALPHA HYDROXYSALMETEROL; AMPHETAMINE; AMPHETAMINE DERIVATIVE; CITALOPRAM; DEBUTYLHALOFANTRINE; DESETHYLOXYBUTYNIN; DINORCITALOPRAM; DRUG METABOLITE; ESMOLOL; FLUOXETINE; HALOFANTRINE; MEPHENYTOIN; METHAMPHETAMINE; MIANSERIN; N ETHYL 3,4 METHYLENEDIOXYMETHAMPHETAMINE; NEFOPAM; NORCITALOPRAM; NORFLUOXETINE; NORMEPHENYTOIN; NORMIANSERIN; NORNEFOPAM; NORSELEGILINE; O GLUCURONYL N ETHYL 4 HYDROXY 3 METHOXYAMPHETAMINE; OXYBUTYNIN; SALMETEROL; SELEGILINE; THIORIDAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; XENOBIOTIC AGENT;

ANALYTIC METHOD; CHIRALITY; CHROMATOGRAPHY; DERIVATIZATION; DIASTEREOISOMER; DRUG ABUSE; DRUG BLOOD LEVEL; DRUG METABOLISM; ELUTION; ENANTIOMER; FORENSIC MEDICINE; GENETIC POLYMORPHISM; HUMAN; MASS SPECTROMETRY; MEDICAL TECHNOLOGY; METABOLITE; MONITORING; NONHUMAN; PHARMACODYNAMICS; PHARMACOGENETICS; QUANTITATIVE ANALYSIS; RACEMIC MIXTURE; REFERENCE VALUE; REVIEW; SENSITIVITY AND SPECIFICITY; SEPARATION TECHNIQUE; STANDARDIZATION; STEREOCHEMISTRY; TOXICOLOGY; VALIDATION PROCESS; ADDICTION; ANIMAL; CHEMISTRY; FEMALE; ISOLATION AND PURIFICATION; METHODOLOGY; PREGNANCY; STEREOISOMERISM;

ANIMALS; CHROMATOGRAPHY; FEMALE; FORENSIC MEDICINE; HUMANS; MASS SPECTROMETRY; PHARMACOGENETICS; PREGNANCY; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM; SUBSTANCE-RELATED DISORDERS; TOXICOLOGY; XENOBIOTICS;

EID: 11844295375     PISSN: 02693879     EISSN: None     Source Type: Journal    
DOI: 10.1002/bmc.447     Document Type: Review

References (65)

1. Ali I and Aboul-Enein HY. Enantioseparation of some clinically used drugs by HPLC using cellulose Tris (3,5-dichlorophenylcarbmate) chiral stationary phase. Biomedical Chromatography 2003; 17: 113-117.
2. Angelo HR, Beck N and Kristensen K. 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. Journal of Chromatography B 1999; 724: 35-40.
3. Baumann P, Zullino DF and Eap CB. Enantiomers' potential in psychopharmacology - a critical analysis with special emphasis on the antidepressant escitalopram. European Journal of Neuropyschopharmacology 2002; 12: 433-444.
4. Birkett DJ. Racemates or enantiomers: regulatory approaches. Clinical Experimental Pharmacology and Physiology 1989; 16: 479-483.
5. Benedetti M, Malina J, Kasparkova J, Barbec V and Natalie G. Chiral discrimination in platinum anticancer drugs. Environmental Health Perspectives 2002; 110: 779-782.
6. Bojarski J. Stereoselective chromatography of cardiovascular drugs: an update. Journal of Biochemical and Biophysics Methods 2002; 54: 197-220.
7. Brandsteterova E and Wainer IW. Achiral and chiral high-performance liquid chromatography of verapamil and its metabolites in serum samples. Journal of Chromatography B 1999; 732: 395-404.
8. Brocks DR. Stereoselective pharmacokinetics of desbutylhalofantrine, a metabolite of halofantrine, in the rat after administration of the racemic metabolite or parent drug. Biopharmaceutics and Drug Disposition 2000; 21: 365-371.
9. Brocks DR. A high performance liquid chromatographic assay for the determination of desbutylhalofantrine enantiomers in rat plasma. Journal of Pharmacology and Pharmaceutical Sciences 2001; 4: 24-31.
10. Brunnenberg M and Kovar KA. Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans. Journal of Chromatography B Biomedical Science Applications 2001; 751: 9-18.
11. Buechler J, Schwab M, Mikus G, Fischer B, Hermle L, Mars C, Gron G, Spitzer M and Kovar K-A. Enantioselective quantitation of the ecstasy compound (R)- and (S)-N ethyl-3,4-methylenedioxyamphetamine and its major metabolites in human plasma and urine. Journal of Chromatography B 2003; 793: 207-232.
12. Burke D and Henderson DJ. Chirality: a blue print for the future. British Journal of Anaesthesia 2002; 88: 563-576.
13. Capka V and Xu Y. Simultaneous determination of enantiomers of structurally related anticholinergic analogs in human serum by liquid chromatography - electrospray ionization mass spectrometry with on-line sample cleanup. Journal of Chromatography B 2001; 762: 181-192.
14. Cerqueira PM, Boralli VB, Coelho EB, Lopes NP, Lopes-Guimaraes LF, Bonato PS and Lanchote VL. Enantioselective determination of metoprolol acidic metabolite in plasma and urine using liquid chromatography chiral columns: application to pharmacokinetics. Journal of Chromatography B 2003; 783: 433-441.
15. Chawla J, Le Guern ME, Alquier C, Kalhorn TF and Levy RH. Effect of route of administration on the pharmacokinetic behavior of enantiomers of nefopam and desmethylnefopam. Therapeutic Drug Monitoring 2003; 25: 203-210.
16. De Camp WH. The FDA perspective on the development of stereoisomers. Chirality 1989; 1: 2-6.
17. De Gaitani MC, Martinez AS and Bonato PS. Racemization and degradation of thioridazine and thioridazine sulfone in human plasma and aqueous solutions. Chirality 2003; 15: 479-485.
18. Gatti G, Bonomi I, Marchiselli R, Fattore C, Spina E, Scordo G, Pacifici R and Perucca E. Improved enantioselective assay for the determination of fluoxetine and norfluoxetine enantiomers in human plasma by liquid chromatography. Journal of Chromatography 2003; 784 375-383.
19. Haginaka J. Pharmaceutical and biomedical applications of enantioseparations using liquid chromatographic techniques. Journal of Pharmaceutical and Biomedical Analysis 2002; 27: 357-372.
20. Hasegawa M, Matsubara K, Fukushima S, Maseda C, Uezono T and Kimura K. Stereoselective analysis of selegiline metabolites: possible urinary markers for selegiline therapy. Forensic Science International 1999; 101: 95-106.
21. Hedeland M, Fredriksson E, Lennernas H and Bondersson U. Simultaneous quantitation of the enantiomers of verapamil and its N demethylated metabolite in human plasma using liquid chromatography - tandem mass spectrometry. Journal of Chromatography B 2004; 804 303-311.
22. Holmgren P, Carlsson B, Zackrisson AL, Lindblom B, Dahl ML, Scordo MG, Druid H and Ahlner J. Enantioselective analysis of citalopram and its metabolites in postmortem blood and genotyping for CYP2D6 and CYP2C19. Journal of Analytical Toxicology 2004; 28: 94-104.
23. Hutt SJ and O'Grady J. Drug chirality: a consideration of the significance of the stereochemistry of antimicrobial agents. Journal of Antimicrobial Agents and Chemotherapy 1996; 37: 7-32.
24. Isoherranen N, Roeder M, Soback S, Yagen B, Schruig V and Bialer M. Enantioselective analysis of levetiracetam and its enantiomer R-α-ethyl-2-oxo-pyrrolidine acetamide using gas chromatography and ion trap mass spectrometric detection. Journal of Chromatography B 2000; 745: 325-332.
25. Jabor VAP, Coelho EB, Ifa DR, Bonato PS, dos Santos NAG and Lanchote VL. Enantioselective determination of lercanidipine in human plasma for pharmacokinetic studies by normal phase liquid chromatography-tandem mass spectrometry. Journal of Chromatography B 2003; 796: 429-437.
26. Jansson B, Simonsson USH and Ashton M. Simultaneous enantiospecific separation and quantitation of mephenytoin and its metabolites nirvanol and 4′-hydroxymephenytoin in human plasma by liquid chromatography. Journal of Chromatography B 2003; 791: 179-191.
27. Kaddoumi A, Nakashima MN and Nakashima K. Fluorometric determination of DL-fenfluramine, DL-norfenfluramine and phentermine in plasma by achiral and chiral high-performance liquid chromatography. Journal of Chromatography B 2001; 763: 79-90.
28. Katsuki H, Hamada A, Nakamura C, Arimori K and Nakano M. High performance liquid chromatographic assay for the simultaneous determination of lansoprazole enantiomers and metabolites in human liver microsomes. Journal of Chromatography B 2001; 757: 127-133.
29. Kim J, Riggs KW and Rurak DW. Stereoselective pharmacokinetics of fluoxetine and norfluoxetine enantiomers in pregnant sheep. Drug Metabolism and Disposition 2004; 32: 212-221.
30. Kim KH, Heo SY, Hong SP and Lee BC. Enantiomeric purity test of bevantolol by reversed-phase high performance liquid chromatography after derivatization with 2,3,4,6-tetra-O acetyl-beta-D-glucopyranosyl isothiocyanate. Archives of Pharmaceutical Research 2000; 23: 568-573.
31. Kim KH, Kim HJ, Kim J-H and Shin SD. Determination of terbutaline enantiomers in human urine by coupled achiral-chiral high-performance liquid chromatography with fluorescence detection. Journal of Chromatography B 2001; 751: 69-77.
32. Lamprecht G, Kraushofer T, Stoschitzky K and Lindner W. Enantioselective analysis of (R)- and (S)-atenolol in urine samples by a high-performance liquid chromatography column-switching setup. Journal of Chromatography B 2000; 740: 219-226.
33. Lanchote VL, Rocha A, Vieira de Albuquerque FU, Coelho EB and Bonato PS. Stereoselective analysis of fluvstatin in human plasma for pharmacokinetic studies. Journal of Chromatography B 2001; 765 81-88.
34. Liang HR, Foltz RL, Meng M and Bennett P. Method development and validation for quantitative determination of methadone enantiomers in human plasma by liquid chromatography/tandem mass spectrometry. Journal of Chromatography B 2004; 806: 91-198.
35. Masubuchi N, Yamazaki H and Tamaka M. Stereoselective chiral inversion of pantoprazole enantiomers after separate doses to rats. Chirality 1998; 10: 737-753.
36. Miura M, Tada H and Suzuki T. Simultaneous determination of lansoprazole enantiomers and their metabolites in plasma by liquid chromatography with solid-phase extraction. Journal of Chromatography B 2004; 804: 389-395.
37. Muralidharan G, Hawes EM, McKay G and Midha KK. Quinine is a more potent inhibitor than quinidine in rat of the oxidative metabolic routes of methoxyphenamine which involve debrisoquin 4-hydroxylase. Xenobiotica 1991; 21: 1441-1450.
38. Mustafa SS, Trivedi R, Mamidi NVSR, Mullangi R and Srinivas NR. Development and validation of a chiral liquid chromatographic method, based on Chiralpak to quantify enantiomers of (+)-DRF 2725 in rat plasma: lack of inversion of ragaglitazar (S(-)-DRF 2725) to its opposite antipode in plasma. Journal of Chromatography B 2004; 809: 23-30.
39. Rentsch K. The importance of stereoselective determination of drugs in the clinical laboratory. Journal of Biochemical Biophysics Methods 2002; 54: 1-9.
40. Rodriguez-Rosas ME, Preston KL, Epstein DH, Moolchan ET and Wainer IW. Quantitative determination of the enantiomers of methadone and its metabolite (EDDP) in human saliva by enantioselective liquid chromatography with mass spectrometric detection. Journal of Chromatography B 2003a; 796: 355-370.
41. Rodriguez-Rosas ME, Patel S and Wainer IW. Determination of the enantiomers of ketamine and norketamine in human plasma by enantioselective liquid chromatography-mass spectrometry. Journal of Chromatography B 2003b; 794: 99-108.
42. Sandstrom R, Lrnnernas H, Ohlen K and Karlsson J. Enantioselective separation of verapamil and norverapamil using Chiral-AGP as the stationary phase. Journal of Pharmaceutical and Biomedical Analysis 1999; 21: 43-49.
43. Srinivas NR. Impact of chirality 1: a look in the miffor from a pharmacokinetic perspective. Indian Journal of Pharmaceutical Sciences 2001; 63: 265-272.
44. Srinivas NR. Evaluation of experimental strategies for the development of chiral chromatographic methods based on diastereomer formation. Biomedical Chromatography 2004a; 18: 207-233.
45. Srinivas NR. Clinical pharmacokinetic data of racemic drugs obtained by the indirect method following precolumn diastereomer formation: is the influence of racemization during chiral derivatization significant? Biomedical Chromatography 2004b; 18: 343-349.
46. Srinivas NR, Hubbard JW, Hawes EM, McKay G and Midha KK. Enantioselective gas chromatographic assays with electroncapture detection for methoxyphenamine and its three primary metabolites in human urine. Journal of Chromatography 1989; 487: 61-72.
47. Srinivas NR, Shyu WC and Barbhaiya RH. Gas chromatographic separation of enantiomers as diastereomers following precolumn derivatization and applications in pharmacokinetic studies: a review. Biomedical Chromatography 1995; 9: 1-9.
48. Srinivas NR, Barbhaiya RH and Midha KK. Enantiomeric drug development: issues, considerations and regulatory requirements. Journal of Pharmaceutical Sciences 2001; 90: 1205-1215.
49. Sun XX, Sun LZ and Aboul-Enein HY. Chiral derivatization reagents for drug enantioseparation by high-performance liquid chromatography based upon pre-column derivatization and formation of diastereomers: enantioselectivity and related structure. Biomedical Chromatography 2001; 15: 116-132.
50. Tang YH, He Y, Yao TW and Zeng S. Simultaneous determination of the enantiomers of esmolol and its acid metabolite in human plasma by reversed phase liquid chromatography with solid-phase extraction. Journal of Chromatography B Analytical Technology Biomedical Lifie Sciences 2004; 805: 249-254.
51. Teng XW, Wang SWJ and Davies NM. Stereospecific high-performance liquid chromatographic analysis of ibuprofen in rat serum. Journal of Chromatography B 2003; 796: 225-231.
52. Toyo'oka T. Resolution of chiral drugs by liquid chromatography based upon diastereomer formation with chiral derivatization reagents. Journal of Biochemical and Biophysics Methods 2002; 54: 25-56.
53. Trejtnar F, Kral R, Pavek P and Wsol V. Stereoselective pharmacokinetics and metabolism of flobufen in guinea pigs. Chirality 2003; 15: 724-729.
54. Ulrich S. Direct stereoselective assay of fluoxetine and norfluoxetine enantiomers in human plasma or serum by two-dimensional gaschromatography with nitrogen-phosphorous selective detection. Journal of Chromatography B 2003; 783: 481-490.
55. Volosov A, Bialer M, Xiadong S, Perucca E, Sintov A and Yagen B. Simultaneous stereoselective high-performance liquid chromatographic determination of 10-hydroxycarbazepine and its metabolite carbamazepine-10,11-trans-dihydrodiol in human urine. Journal of Chromatography B 2000; 738: 419-425.
56. Wainer IW. The therapeutic Promise of single enantiomers: introduction. Human Psychopharmacology 2001; 16: 67-71.
57. Ward TJ. Chiral separations. Analytical Chemistry 2002; 7: 2863-2872.
58. Williams ML and Wainer IW. Role of chiral chromatography in therapeutic drug monitoring and in clinical and forensic toxicology. Therapeutic Drug Monitoring 2002; 24: 290-296.
59. Wu Z, Upadhyaya P, Carmella SG, Hecht SS and Zimmermann CL. Dispostion of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in bile duct-cannulated rats: stereoselective metabolism and tissue distribution. Carcinogenesis 2002; 23: 171-179.
60. Xia Y-Q, Bakhtiar R and Franklin RB. Automated online dualcolumn extraction coupled with teicoplanin stationary phase for simultaneous determination of (R)- and (S)-propranolol in rat plasma using liquid chromatography-tandem mass spectrometry. Journal of Chromatography B 2003; 788: 317-329.
61. Yanagihara Y, Ohtani M, Kariya S, Uchino K, Aoyoma T, Yamamura Y and Iga T. Stereoselective high-performance liquid chromatographic determination of ketamine and its active metabolite, norketamine, in human serum. Journal of Chromatography B 2000; 746: 227-231.
62. Yasui N, Tybring G, Otani K, Mihara K, Suzuki A, Svensson JO and Kaneko S. Effect of thioridazine, an inhibitor of CYP2D6, on the steady state plasma concentrations of the enantiomers of mianserin and its active metabolite, desmethylmianserin, in depressed Japanese patients. Pharmacogenetics 1997; 7: 369-374.
63. Zhang M, Fawcett P and Shaw JP. Rapid chiral high-performance liquid chromatographic assay for salmetrol and α-hydroxysalmetrol. Application to in vitro metabolism studies. Journal of Chromatography B 1999; 729: 225-230.
64. Zhong D and Chen X. Enantioselective determination of propafenone and its metabolites in human plasma by liquid chromatography-mass spectrometry. Journal of Chromatography B 1999; 721: 67-75.
65. Zobrist RH, Schmid B, Feick A, Quan D and Sanders SW. Pharmacokinetics of the R- and S-enantiomers of oxybutynin and N-desethyloxybutynin following oral and transdermal administration of the racemate in healthy volunteers. Pharmaceutical Research 2001; 18: 1029-1034.