Chiral drug analysis using mass spectrometric detection relevant to research and practice in clinical and forensic toxicology

Journal of Chromatography A

Volumn 1269, Issue , 2012, Pages 122-135

  Schwaninger, Andrea E ^a   Meyer, Markus R ^b   Maurer, Hans H ^b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

Chiral drug analysis; Clinical toxicology; Forensic toxicology

Indexed keywords

ANALYTICAL APPROACH; ANALYTICAL RESULTS; CAPILLARY ELECTROMIGRATION; CHIRAL ANALYTES; CHIRAL DRUGS; CLINICAL TOXICOLOGY; DESIGNER DRUGS; FORENSIC TOXICOLOGY; MASS SPECTROMETRIC DETECTION; SEPARATION SYSTEMS; SUPER CRITICAL FLUID CHROMATOGRAPHY; TRAMADOL; TYPICAL APPLICATION;

GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

ENANTIOMERS;

AMPHETAMINE; AMPHETAMINE DERIVATIVE; ANTICOAGULANT AGENT; CARDIOVASCULAR AGENT; CENTRAL STIMULANT AGENT; METHADONE; PHENPROCOUMON; PSYCHOTROPIC AGENT; TRAMADOL; WARFARIN;

CAPILLARY ELECTROCHROMATOGRAPHY; CHIRALITY; CLINICAL RESEARCH; DRUG CLASSIFICATION; DRUG DETERMINATION; ENANTIOMER; FORENSIC TOXICOLOGY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; INTERMETHOD COMPARISON; MASS SPECTROMETRY; PRIORITY JOURNAL; REACTION TIME; REVIEW; SENSITIVITY ANALYSIS; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; STEREOCHEMISTRY; SUPERCRITICAL FLUID CHROMATOGRAPHY;

CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, LIQUID; CHROMATOGRAPHY, SUPERCRITICAL FLUID; ELECTROPHORESIS, CAPILLARY; FORENSIC TOXICOLOGY; MASS SPECTROMETRY; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM;

EID: 84870346190     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2012.07.045     Document Type: Review

References (154)

1. Smith S.W. Toxicol. Sci. 2009, 110:4.
2. Sekhon B.S. Int. J. Pharm. Technol. Res. 2010, 2:1584.
3. Rentsch K.M. J. Biochem. Biophys. Methods 2002, 54:1.
4. Fan H.R., Zhang W. Asian J. Drug Met. Pharmacokinet. 2005, 5:169.
5. Brocks D.R. Biopharm. Drug Dispos. 2006, 27:387.
6. Lu H. Expert Opin. Drug Metab. Toxicol. 2007, 3:149.
7. Marzo A., Heftmann E. J. Biochem. Biophys. Methods 2002, 54:57.
8. Li X.Q., Weidolf L., Simonsson R., Andersson T.B. J. Pharmacol. Exp. Ther. 2005, 315:777.
9. Hiemke C., Baumann P., Bergemann N., Conca A., Dietmaier O., Egberts K., Fric M., Gerlach M., Greiner C., Grunder G., Haen E., Havemann-Reinecke U., Jaquenoud S.E., Kirchherr H., Laux G., Lutz U.C., Messer T., Muller M.J., Pfuhlmann B., Rambeck B., Riederer P., Schoppek B., Stingl J., Uhr M., Ulrich S., Waschgler R., Zernig G. Pharmacopsychiatry 2011, 44:195.
10. Srinivas N.R. Biomed. Chromatogr. 2004, 18:759.
11. Court M.H., Hao Q., Krishnaswamy S., Bekaii-Saab T., Al Rohaimi A., von Moltke L.L., Greenblatt D.J. J. Pharmacol. Exp. Ther. 2004, 310:656.
12. Jansson B., Elsherbiny D., Simonsson U.S. Rapid Commun. Mass Spectrom. 2006, 20:463.
13. Martens-Lobenhoffer J., Reiche I., Troger U., Monkemuller K., Malfertheiner P., Bode-Boger S.M. J. Chromatogr. B 2007, 857:301.
14. Ward T.J. Anal. Chem. 2002, 74:2863.
15. Ward T.J., Hamburg D.M. Anal. Chem. 2004, 76:4635.
16. Ward T.J. Anal. Chem. 2006, 78:3947.
17. Ward T.J., Baker B.A. Anal. Chem. 2008, 80:4363.
18. Ward T.J., Ward K.D. Anal. Chem. 2010, 82:4712.
19. Ward T.J., Ward K.D. Anal. Chem. 2012, 84:626.
20. Srinivas N.R. Biomed. Chromatogr. 2006, 20:383.
21. Williams M.L., Wainer I.W. Ther. Drug Monit. 2002, 24:290.
22. Kumar A.P., Jin D. Appl. Spectrosc. Rev. 2009, 44:267.
23. Maurer H.H. Experientia 2010, 100:317.
24. Kelly T., Doble P., Dawson M. J. Chromatogr. B 2005, 814:315.
25. Pizarro N., Farre M., Pujadas M., Peiro A.M., Roset P.N., Joglar J., de la Torre R. Drug Metab. Dispos. 2004, 32:1001.
26. Wan Raihana W.A., Gan S.H., Tan S.C. J. Chromatogr. B 2011, 879:8.
27. Pizarro N., de la T.R., Farre M., Segura J., Llebaria A., Joglar J. Bioorg. Med. Chem. 2002, 10:1085.
28. Meyer M.R., Peters F.T., Maurer H.H. Drug Metab. Dispos. 2008, 36:2345.
29. Schwaninger A.E., Meyer M.R., Huestis M.A., Maurer H.H. J. Mass Spectrom. 2011, 46:603.
30. Maurer H.H., Pfleger K., Weber A.A. Mass Spectral and GC Data of Drugs, Poisons, Pesticides, Pollutants and their Metabolites 2011, Wiley-VCH, Weinheim.
31. Soderholm S.L., Damm M., Kappe C.O. Mol. Divers. 2010, 14:869.
32. Kraemer T., Roditis S.K., Peters F.T., Maurer H.H. J. Anal. Toxicol. 2003, 27:68.
33. Li L., Everhart T., Jacob I.P., Jones R., Mendelson J. Br. J. Clin. Pharmacol. 2010, 69:187.
34. Chytil L., Sticha M., Matouskova O., Perlik F., Slanar O. J. Chromatogr. B 2009, 877:1937.
35. Nystrom I., Trygg T., Woxler P., Ahlner J., Kronstrand R. J. Anal. Toxicol. 2005, 29:682.
36. Wang S.M., Wang T.C., Giang Y.S. J. Chromatogr. B 2005, 816:131.
37. Strano-Rossi S., Botre F., Bermejo A.M., Tabernero M.J. Forensic Sci. Int. 2009, 193:95.
38. LeVasseur N.L., Zhu H.J., Markowitz J.S., DeVane C.L., Patrick K.S. J. Chromatogr. B 2008, 862:140.
39. Holler J.M., Vorce S.P., Bosy T.Z., Jacobs A. J. Anal. Toxicol. 2005, 29:652.
40. Paul B.D., Jemionek J., Lesser D., Jacobs A., Searles D.A. J. Anal. Toxicol. 2004, 28:449.
41. Peters F.T., Kraemer T., Maurer H.H. Clin. Chem. 2002, 48:1472.
42. Pizarro N., Llebaria A., Cano S., Joglar J., Farre M., Segura J., de la Torre R. Rapid Commun. Mass Spectrom. 2003, 17:330.
43. Leis H.J., Windischhofer W. J. Chromatogr. B 2011, 879:2299.
44. Peters F.T. Clin. Biochem. 2011, 44:54.
45. Meyer M.R., Maurer H.H. Anal. Bioanal. Chem. 2012, 402:195.
46. Meyer M.R., Maurer H.H. Anal. Bioanal. Chem. 2012, 403:1221.
47. Hoffmann C.V., Laemmerhofer M., Lindner W. J. Chromatogr. A 2007, 1161:242.
48. Hoffmann C.V., Lammerhofer M., Lindner W. Anal. Bioanal. Chem. 2009, 393:1257.
49. Jabor V.A., Coelho E.B., Ifa D.R., Bonato P.S., Dos Santos N.A., Lanchote V.L. J. Chromatogr. B 2003, 796:429.
50. Lindmark B., Ahnoff M., Persson B.A. J. Pharm. Biomed. Anal. 2002, 27:489.
51. Fried K.M., Young A.E., Usdin Y.S., Wainer I.W. J. Pharm. Biomed. Anal. 2002, 27:479.
52. Yang E., Wang S., Kratz J., Cyronak M.J. J. Pharm. Biomed. Anal. 2004, 36:609.
53. Szeitz A., Edginton A.N., Peng H.T., Cheung B., Riggs K.W. Am. J. Anal. Chem. 2010, 2:47.
54. John H., Eyer F., Zilker T., Thiermann H. Anal. Chim. Acta 2010, 680:32.
55. Hou J., Zheng J., Shamsi S.A. J. Chromatogr. A 2007, 1159:208.
56. Jiang H., Randlett C., Junga H., Jiang X., Ji Q.C. J. Chromatogr. B 2009, 877:173.
57. Zuo Z., Wo S.K., Lo C.M., Zhou L., Cheng G., You J.H. J. Pharm. Biomed. Anal. 2010, 52:305.
58. Kingback M., Josefsson M., Karlsson L., Ahlner J., Bengtsson F., Kugelberg F.C., Carlsson B. J. Pharm. Biomed. Anal. 2010, 53:583.
59. Remane D., Wissenbach D.K., Meyer M.R., Maurer H.H. Rapid Commun. Mass Spectrom. 2010, 24:859.
60. Remane D., Meyer M.R., Wissenbach D.K., Maurer H.H. Rapid Commun. Mass Spectrom. 2010, 24:3103.
61. Kammerer B., Kahlich R., Ufer M., Laufer S., Gleiter C.H. Anal. Biochem. 2005, 339:297.
62. Ufer M., Kammerer B., Kahlich R., Kirchheiner J., Yasar U., Brockmoller J., Rane A. Xenobiotica 2004, 34:847.
63. Carvalho T.M., Cavalli R.C., Marques M.P., Da Cunha S.P., Baraldi C.O., Lanchote V.L. Chirality 2009, 21:738.
64. Poggi J.C., Da Silva F.G., Coelho E.B., Marques M.P., Bertucci C., Lanchote V.L. Chirality 2012, 24:209.
65. Siluk D., Mager D.E., Gronich N., Abernethy D., Wainer I.W. J. Chromatogr. B 2007, 859:213.
66. Streel B., Laine C., Zimmer C., Sibenaler R., Ceccato A. J. Biochem. Biophys. Methods 2002, 54:357.
67. Kang S.W., Jang H.J., Moore V.S., Park J.Y., Kim K.A., Youm J.R., Han S.B. J. Chromatogr. B 2010, 878:3351.
68. Liu K., Dai X., Zhong D., Chen X. J. Chromatogr. B 2008, 864:129.
69. Meng M., Rohde L., Capka V., Carter S.J., Bennett P.K. J. Pharm. Biomed. Anal. 2010, 53:973.
70. Caslavska J., Thormann W. J. Chromatogr. A 2011, 1218:588.
71. Wang B., He J., Shamsi S.A. J. Chromatogr. Sci. 2010, 48:572.
72. De Klerck K., Mangelings D., Vander H.Y. J. Pharm. Biomed. Anal. 2012, 10.1016/j.jpba.2012.01.021.
73. Kraemer T., Maurer H.H. Ther. Drug Monit. 2002, 24:277.
74. de la Torre R., Farre M., Roset P.N., Pizarro N., Abanades S., Segura M., Segura J., Cami J. Ther. Drug Monit. 2004, 26:137.
75. Kraemer T., Maurer H.H. J. Chromatogr. B 1998, 713:163.
76. Musshoff F. Drug Metab. Rev. 2000, 32:15.
77. Iio R., Chinaka S., Tanaka S., Takayama N., Hayakawa K. Analyst 2003, 128:646.
78. Iio R., Chinaka S., Takayama N., Hayakawa K. J. Health Sci. 2005, 51:693.
79. Nishida K., Itoh S., Inoue N., Kudo K., Ikeda N. J. Anal. Toxicol. 2006, 30:232.
80. Peters F.T., Samyn N., Lamers C., Riedel W., Kraemer T., de Boeck G., Maurer H.H. Clin. Chem. 2005, 51:1811.
81. Meyer M.R., Maurer H.H. Chem. Res. Toxicol. 2009, 22:1205.
82. Schwaninger A.E., Meyer M.R., Zapp J., Maurer H.H. Drug Metab. Dispos. 2009, 37:2212.
83. Schwaninger A.E., Meyer M.R., Maurer H.H. Drug Metab. Dispos. 2011, 39:1998.
84. Schwaninger A.E., Meyer M.R., Barnes A.J., Kolbrich-Spargo E.A., Gorelick D.A., Goodwin R.S., Huestis M.A., Maurer H.H. Biochem. Pharmacol. 2012, 83:131.
85. Schwaninger A.E., Meyer M.R., Zapp J., Maurer H.H. Toxicol. Lett. 2012, 212:38.
86. Meyer M.R., Peters F.T., Maurer H.H. Drug Metab. Dispos. 2009, 37:1152.
87. Meyer M.R., Peters F.T., Maurer H.H. Biochem. Pharmacol. 2009, 77:1725.
88. Meyer M.R., Peters F.T., Maurer H.H. Toxicol. Lett. 2009, 190:54.
89. Peters F.T., Samyn N., Wahl M., Kraemer T., de Boeck G., Maurer H.H. J. Anal. Toxicol. 2003, 27:552.
90. Fujii H., Hara K., Kageura M., Kashiwagi M., Matsusue A., Kubo S. Forensic Toxicol. 2009, 27:75.
91. Tao Q.F., Zeng S. J. Biochem. Biophys. Methods 2002, 54:103.
92. Martins L., Yegles M., Chung H., Wennig R. J. Chromatogr. B 2005, 825:57.
93. Martins L.F., Yegles M., Chung H., Wennig R. J. Chromatogr. B 2006, 842:98.
94. Martins L.F., Yegles M., Samyn N., Ramaekers J.G., Wennig R. Forensic Sci. Int. 2007, 172:150.
95. Peters F.T., Samyn N., Kraemer T., Riedel W., Maurer H.H. Clin. Chem. 2007, 53:702.
96. Rasmussen L.B., Olsen K.H., Johansen S.S. J. Chromatogr. B 2006, 842:136.
97. Aasim W.R., Gan S.H., Tan S.C. Biomed. Chromatogr. 2008, 22:1035.
98. Herraez-Hernandez R., Campins-Falco P., Verdu-Andres J. J. Biochem. Biophys. Methods 2002, 54:147.
99. Schappler J., Guillarme D., Prat J., Veuthey J.L., Rudaz S. Electrophoresis 2008, 29:2193.
100. Eap C.B., Buclin T., Baumann P. Clin. Pharmacokinet. 2002, 41:1153.
101. Rodriguez-Rosas M.E., Medrano J.G., Epstein D.H., Moolchan E.T., Preston K.L., Wainer I.W. J. Chromatogr. A 2005, 1073:237.
102. Buchard A., Linnet K., Johansen S.S., Munkholm J., Fregerslev M., Morling N. J. Forensic Sci. 2010, 55:457.
103. Crettol S., Digon P., Golay K.P., Brawand M., Eap C.B. Pharmacology 2007, 80:304.
104. Moody D.E., Lin S.N., Chang Y., Lamm L., Greenwald M.K., Ahmed M.S. J. Anal. Toxicol. 2008, 32:208.
105. Totah R.A., Allen K.E., Sheffels P., Whittington D., Kharasch E.D. J. Pharmacol. Exp. Ther. 2007, 321:389.
106. Totah R.A., Sheffels P., Roberts T., Whittington D., Thummel K., Kharasch E.D. Anesthesiology 2008, 108:363.
107. Chang Y., Fang W.B., Lin S.N., Moody D.E. Basic Clin. Pharmacol. Toxicol. 2011, 108:55.
108. Johansen S.S., Linnet K. J. Anal. Toxicol. 2008, 32:499.
109. Whittington D., Sheffels P., Kharasch E.D. J. Chromatogr. B 2004, 809:313.
110. Rodriguez-Rosas M.E., Lofwall M.R., Strain E.C., Siluk D., Wainer I.W. J. Chromatogr. B 2007, 850:538.
111. Etter M.L., George S., Graybiel K., Eichhorst J., Lehotay D.C. Clin. Biochem. 2005, 38:1095.
112. Liang H.R., Foltz R.L., Meng M., Bennett P. J. Chromatogr. B 2004, 806:191.
113. Foster D.J., Morton E.B., Heinkele G., Murdter T.E., Somogyi A.A. Ther. Drug Monit. 2006, 28:559.
114. Ansermot N., Rudaz S., Brawand-Amey M., Fleury-Souverain S., Veuthey J.L., Eap C.B. J. Chromatogr. B 2009, 877:2301.
115. de Moraes N.V., Lauretti G.R., Napolitano M.N., Santos N.R., Godoy A.L., Lanchote V.L. J. Chromatogr. B 2012, 880:140.
116. Campanero M.A., Garcia-Quetglas E., Sadaba B., Azanza J.R. J. Chromatogr. A 2004, 1031:219.
117. Kirchheiner J., Keulen J.T., Bauer S., Roots I., Brockmoller J. J. Clin. Psychopharmacol. 2008, 28:78.
118. Pedersen R.S., Damkier P., Brosen K. Eur. J. Clin. Pharmacol. 2006, 62:513.
119. Garcia-Quetglas E., Azanza J.R., Sadaba B., Munoz M.J., Gil I., Campanero M.A. Pharmacol. Res. 2007, 55:122.
120. Lehtonen P., Sten T., Aitio O., Kurkela M., Vuorensola K., Finel M., Kostiainen R. Eur. J. Pharm. Sci. 2010, 41:523.
121. Chytil L., Matouskova O., Cerna O., Pokorna P., Vobruba V., Perlik F., Slanar O. J. Chromatogr. B 2010, 878:481.
122. Musshoff F., Madea B., Stuber F., Stamer U.M. J. Anal. Toxicol. 2006, 30:463.
123. Holliday S.M., Benfield P. Drugs 1995, 49:280.
124. Rocha A., Marques M.P., Coelho E.B., Lanchote V.L. Chirality 2007, 19:793.
125. Coles R., Kharasch E.D. J. Chromatogr. B 2007, 857:67.
126. Coles R., Kharasch E.D. Pharm. Res. 2008, 25:1405.
127. Bratton S.M., Mosher C.M., Khallouki F., Finel M., Court M.H., Moran J.H., Radominska-Pandya A. J. Pharmacol. Exp. Ther. 2012, 340:46.
128. Kammerer B., Kahlich R., Ufer M., Schenkel A., Laufer S., Gleiter C.H. Anal. Bioanal. Chem. 2005, 383:909.
129. Coe R.A., Rathe J.O., Lee J.W. J. Pharm. Biomed. Anal. 2006, 42:573.
130. Kammerer B., Kahlich R., Ufer M., Laufer S., Gleiter C.H. Rapid Commun. Mass Spectrom. 2004, 18:458.
131. Kirchheiner J., Ufer M., Walter E.C., Kammerer B., Kahlich R., Meisel C., Schwab M., Gleiter C.H., Rane A., Roots I., Brockmoller J. Pharmacogenetics 2004, 14:19.
132. Zheng J., Shamsi S.A. Anal. Chem. 2003, 75:6295.
133. Redman A.R., Zheng J., Shamsi S.A., Huo J., Kelly E.J., Ho R.J., Ritchie D.M., Hon Y.Y. Clin. Appl. Thromb. Hemost. 2008, 14:29.
134. Kim K.H., Lee J.H., Ko M.Y., Shin K.S., Kang J.S., Mar W.C., Youm J.R. Chromatographia 2002, 55:81.
135. Badaloni E., D'Acquarica I., Gasparrini F., Lalli S., Misiti D., Pazzucconi F., Sirtori C.R. J. Chromatogr. B 2003, 796:45.
136. Fang L., Bykowski-Jurkiewicz C., Sarver J.G., Erhardt P.W. J. Chromatogr. B 2010, 878:2449.
137. Jiang H., Jiang X., Ji Q.C. J. Chromatogr. B 2008, 872:121.
138. Bonato P.S., Del Lama M.P., de C.R. J. Chromatogr. B 2003, 796:413.
139. Musshoff F., Madea B., Stuber F., Stamer U.M. J. Anal. Toxicol. 2010, 34:581.
140. Servais A.C., Fillet M., Mol R., Somsen G.W., Chiap P., de Jong G.J., Crommen J. J. Pharm. Biomed. Anal. 2006, 40:752.
141. Rodriguez-Rosas M.E., Patel S., Wainer I.W. J. Chromatogr. B 2003, 794:99.
142. Leis H.J., Rechberger G.N., Fauler G., Windischhofer W. Rapid Commun. Mass Spectrom. 2003, 17:569.
143. Schwaninger A.E., Meyer M.R., Barnes A.J., Kolbrich-Spargo E.A., Gorelick D.A., Goodwin R.S., Huestis M.A., Maurer H.H. Clin. Chem. 2011, 57:1748.
144. Sghendo L., Mifsud J., Ellul-Micallef R., Portelli J., Millership J.S. J. Chromatogr. B 2002, 772:307.
145. Shen Z., Wang S., Bakhtiar R. Rapid Commun. Mass Spectrom. 2002, 16:332.
146. Moaddel R., Venkata S.L., Tanga M.J., Bupp J.E., Green C.E., Iyer L., Furimsky A., Goldberg M.E., Torjman M.C., Wainer I.W. Talanta 2010, 82:1892.
147. Leis H.J., Schutz H., Windischhofer W. Anal. Bioanal. Chem. 2011, 400:2663.
148. de Santana F.J., Bonato P.S. Anal. Chim. Acta 2008, 606:80.
149. de Santana F.J., Jabor V.A., Cesarino E.J., Lanchote V.L., Bonato P.S. J. Sep. Sci. 2010, 33:268.
150. Paus E., Jonzier-Perey M., Cochard N., Eap C.B., Baumann P. Ther. Drug Monit. 2004, 26:366.
151. Ohman D., Cherma M.D., Norlander B., Bengtsson F. Ther. Drug Monit. 2003, 25:174.
152. Kang W., Bae K., Noh K. J. Pharm. Biomed. Anal. 2010, 51:264.
153. Kingback M., Karlsson L., Zackrisson A.L., Carlsson B., Josefsson M., Bengtsson F., Ahlner J., Kugelberg F.C. Forensic Sci. Int. 2012, 214:124.
154. Liu W., Wang F., Li H.D. J. Chromatogr. B 2007, 850:183.