HPLC Method for Simultaneous Determination of 1,4-Benzodiazepines and Tricyclic Antidepressants in Pharmaceutical Formulations and Saliva—A Useful Tool in Medicinal Chemistry

REFERENCES

• Haefely , W. ; Parnham , M. ; Bruinvals , J. Discoveries in Pharmacology , Vol. 1 ; Elsevier : Amsterdam , 1983 ; 239 – 306 .
   Google Scholar
• Laurence , D.R. ; Bennett , P.N. Clinical Pharmacology, , 5th Ed. ; McGraw-Hill : New York , 1980 ; 224 – 275 .
   Google Scholar
• Linoila , M. In The Benzodiazepines from Molecular Biology to Clinical Practice ; Costa , E. , Ed.; Raven : New York , 1983 , 267 .
   Google Scholar
• Greenblatt , D.J. ; Shader , R.I. (Editors), Benzodiazepines in Clinical Practice , Raven Press : New York , 1974 ; 61 .
   Google Scholar
• Mazhar , M. ; Binder , S.R. Analysis of benzodiazepines and tricyclic antidepressants in serum using a common solid-phase clean up and a common mobile phase . J. Chromatogr. 1989 , 497 , 201 – 212 .
   PubMed Web of Science ®Google Scholar
• Drummer , O.H. Benzodiazepines-effects on human performance and behaviour . Foren. Sci. Rev. 2002 , 14 , 1 – 14 .
   PubMedGoogle Scholar
• Drummer , O.H. ; Ranson , D.L. Sudden death and benzodiazepines . Am. J. Foren. Med. Pathol. 1996 , 17 , 336 – 342 .
   PubMed Web of Science ®Google Scholar
• Silverman , G. ; Braithwaite , R.A. Benzodiazepines and tricyclic antidepressant plasma levels . Brit. Med. J. 1973 , 7 , 18 – 20 .
   Google Scholar
• McIntyre , I.M. ; Syrjanen , M.L. ; Crump , K. ; Horomidis , S. ; Peace , A.W. ; Drummer , O.H. Simultaneous HPLC gradient analysis of 15 benzodiazepines and selected metabolites in postmortem blood . J. Anal. Toxicol. 1993 , 17 , 202 – 207 .
   PubMedGoogle Scholar
• Ferrara , S.D. ; Tedeschi , L. ; Frison , G. ; Castagna , F. Solid-phase extraction and HPLC-UV confirmation of drugs of abuse in urine . J. Anal. Toxicol. 1992 , 16 , 217 – 222 .
   Google Scholar
• LeBeau , M. ; Hearn , W.L. ; Baselt , R. ; Cone , E. ; Finkle , B. ; Fraser , D. ; Jenkins , A. ; Mayer , J. ; Negrusz , A. ; Poklis , A. ; Walls , H.C. ; Raymon , L. ; Robertson , M. ; Saady , J. Recommendations for toxicological investigations of drug-facilitated sexual assaults . J. Foren. Sci. 1999 , 44 , 227 – 230 .
   PubMed Web of Science ®Google Scholar
• Laloup , M. ; Fernandez , M.M.R. ; Wood , M. ; Maes , V. ; De Boeck , G. ; Vanbeckevoort , Y. ; Samyn , N. Detection of diazepam in urine, hair and preserved oral fluid samples with LC-MS-MS after single and repeated administration of myolastan and valium . Anal. Bioanal. Chem. 2007 , 388 , 1545 – 1556 .
   PubMed Web of Science ®Google Scholar
• Concheiro , M. ; Villain , M. ; Bouchet , S. ; Ludes , B. ; Lopez-Rivadulla , M. ; Kintz , P. Windows of detection of tetrazepam in urine, oral fluid, beard, and hair, with a special focus on drug-facilitated crimes . Ther. Drug Monit. 2005 , 27 , 565 – 570 .
   Google Scholar
• Samyn , N. ; Verstraete , A. ; van Haeren , C. ; Kintz , P. Analysis of drugs of abuse in saliva . Foren. Sci. Rev. 1999 , 11 , 1 – 19 .
   PubMedGoogle Scholar
• Link , B. ; Haschke , M. ; Wenk , M. ; Krahenbuh , S. Determination of midazolam and its hydroxyl metabolites in human plasma and oral fluid by liquid chromatography/electrospray ionization ion trap tandem mass spectrometry . Rapid Commun. Mass Spectrom. 2007 , 21 , 1531 – 1540 .
   PubMed Web of Science ®Google Scholar
• Kintz , P. ; Villain , M. ; Cirimele , V. ; Pépin , G. ; Ludes , B. Windows of detection of lorazepam in urine, oral fluid and hair with a special focus on drug-facilitated crimes . Foren. Sci. Int. 2004 , 145 , 131 – 135 .
   PubMed Web of Science ®Google Scholar
• Atta-Politou , J. ; Parissi-Poulou , M. ; Dona , A. ; Koutselinis , A. A modified simple and rapid reversed phase liquid chromatographic method for quantification of diazepam and nordiazepam in plasma. J. Pharm. Biomed. Anal. 1999, 20, 389–396.
   PubMed Web of Science ®Google Scholar
• El Mahjoub , A. ; Staub , C. High-performance liquid chromatography determination of flunitrazepam and its metabolites in plasma by use of column switching technique: comparison of two extraction columns . J. Chromatogr. B 2001 , 754 , 271 – 283 .
   Google Scholar
• Chéze , M. ; Villain , M. ; Pépin G. Determination of bromazepam, clonazepam and metabolites after a single intake in urine and hair by LC–MS/MS application to forensic cases of drug facilitated crimes . Foren. Sci. Int. 2004 , 145 , 123 – 130 .
   PubMed Web of Science ®Google Scholar
• Negrusz , A. ; Bowen , A.M. ; Moore , C.M. ; Dowd , S.M. ; Strong , M.J. ; Janicak , P.G. Deposition of 7-aminoclonazepam and clonazepam in hair following a single dose of klonopin . J. Anal. Toxicol. 2002 , 26 , 471 – 478 .
   PubMed Web of Science ®Google Scholar
• Meyer , F.P. Indicative therapeutic and toxic drug concentrations in plasma: a tabulation . Int. J. Clin. Pharm. Ther. 1994 , 32 , 71 – 81 .
   PubMed Web of Science ®Google Scholar
• Samyn , N. ; De Boeck , G. ; Cirimele , V. ; Verstraete , A. ; Kintz , P. Detection of flunitrazepam and 7-aminoflunitrazepam in oral fluid after controlled administration of rohypnol . J. Anal. Toxicol. 2002 , 26 , 211 – 215 .
   PubMed Web of Science ®Google Scholar
• Nudelman , N.S. ; Cabrera , C.G. Spectrofluorimetric assay for the photodegradation products of alprazolam . J. Pharm. Biomed. Anal. 2002 , 30 , 887 – 893 .
   PubMed Web of Science ®Google Scholar
• Kintz , P. ; Villain , M. ; Chéze , M. ; Pépin , G. Identification of alprazolam in hair in two cases of drug-facilitated incidents . Foren. Sci. Int. 2005 , 153 , 222 – 226 .
   Google Scholar
• Zhu , H. ; Luo , J. A fast and sensitive liquid chromatographic–tandem mass spectrometric method for assay of lorazepam and application to pharmacokinetic analysis . J. Pharm. Biomed. Anal. 2005 , 39 , 268 – 274 .
   Google Scholar
• Salem , A.A. ; Barsoum , B.N. ; Izake , E.L. Spectrophotometric and fluorimetric determination of diazepam, bromazepam and clonazepam in pharmaceutical and urine samples . Specrochim. Acta Part A: Mol. Biomol. Spectr. 2004 , 60 , 771 – 780 .
   PubMed Web of Science ®Google Scholar
• Labat , L. ; Dallet , P. ; Kummer , E. ; Dubost , J.P. Spectrophotometric, spectrofluorimetric, HPLC and CZE determination of mirtazapine in pharmaceutical tablets . J. Pharm. Biomed. Anal. 2002 , 28 , 365 – 371 .
   PubMed Web of Science ®Google Scholar
• Salem , A.A. ; Barsoum , B.N. ; Izake , E.L. Potentiometric determination of diazepam, bromazepam and clonazepam using solid contact ion-selective electrodes . Anal. Chim. Acta. 2003 , 498 , 79 – 91 .
   Google Scholar
• Carmona , M. ; Silva , M. ; Perezbendito , D. Indirect kinetic catalytic determination of organic compounds: analysis for bromazepam by the stopped-flow technique . J. Microchem. 1993 , 48 , 50 – 59 .
   Google Scholar
• Cantú , M.D. ; Hillebrand , S. ; Queiroz , M.E.C. ; Lanças , F.M. ; Carrilho , E. Validation of non-aqueous capillary electrophoresis for simultaneous determination of four tricyclic antidepressants in pharmaceutical formulations and plasma samples . J. Chromatogr. B 2004 , 799 , 127 – 132 .
   PubMed Web of Science ®Google Scholar
• Lozano-Chaves , M.E. ; Palacios-Santander , J.M. ; Cubillana-Aguilera , L.M. ; Naranjo-Rodriguez , I. ; Hidalgo-Hidalgo-de-Cisneros , J.L. Modified carbon-paste electrodes as sensors for the determination of 1,4-Benzodiazepines: Application to the determination of diazepam and oxazepam in biological fluids. Sens. Actuators B Chem. 2006, 115, 575–583.
   Google Scholar
• Fraser , A.D. ; Meatherall , R. Comparative evaluation of five immunoassays for the analysis of alprazolam and triazolam metabolites in urine: Effect of lowering the screening and GC-MS cut-off values . J. Anal. Toxicol. 1996 , 20 ( 4 ), 217 – 223 .
   PubMed Web of Science ®Google Scholar
• Melanson , S.E.F. ; Lee Lewandrowski , E. ; Griggs , D.A. ; Flood J.G. Interpreting tricyclic antidepressant measurements in urine in an emergency department setting: Comparison of two qualitative point-of-vare urine tricyclic antidepressant drug immunoassays with quantitative serum chromatographic analysis . J. Anal. Toxicol. 2007 , 31 , 270 – 275 .
   Google Scholar
• Nishikawa , T. ; Ohtani , H. ; Herold , D.A. ; Fitzgerald , R.L. Comparison of assay methods for benzodiazepines in urine . A Receptor Assay, Two Immunoassays, and Gas Chromatography-mass Spectrometry. Am. J. Clin. Pathol. 1997 , 107 ( 3 ), 345 – 352 .
   Google Scholar
• Bakavoli , M. ; Kaykhaii , M. Quantitative determination of diazepam, nitrazepam and flunitrazepam in tablets using thin-layer chromatography-densitometry technique . J. Pharm. Biomed. Anal. 2003 , 31 , 1185 – 1189 .
   Google Scholar
• Maślanka , A. ; Krzek , J. Densitometric high performance thin-layer chromatography identification and quantitative analysis of psychotropic drugs . JAOAC Int. 2005 , 88 ( 1 ), 70 – 79 .
   Google Scholar
• Toyooka , T. ; Kumaki , Y. ; Kanbori , M. ; Kato , M. ; Nakahara , Y. Determination of hypnotic benzodiazepines (alprazolam, estazolam, and midazolam) and their metabolites in rat hair and plasma by reversed-phase liquid-chromatography with electrospray ionization mass spectrometry . J. Pharm. Biomed. Anal. 2003 , 30 , 1773 – 1787 .
   Google Scholar
• Gritti , F. ; Guiochon , G. Separation mechanism of nortriptyline and amytriptyline in RPLC . J. Chromatog. A 2005 , 1090 , 39 – 57 .
   Google Scholar
• Óconnor , D. ; Mortishire-Smith , R. ; Morrison , D. ; Davies , A. ; Dominguez , M. Ultra-performance liquid chromatography coupled to time-of-flight mass spectrometry for robust, high-throughput quantitative analysis of an automated metabolic stability assay, with simultaneous determination of metabolic data . J. Chromatog. A 2006 , 20 , 851 – 857 .
   Google Scholar
• Oteen , H.H. ; Zeinab , A.S. Comparison of CZE, MEKC, MEEKC and non-aqueous capillary electrophoresis for the determination of impurities in bromazepam . J. Pharm. Biomed. Anal. 2005 , 39 , 322 – 327 .
   Google Scholar
• Devasish , B. ; Abhilasha , D. ; Martinavarro-Dominguez , A. ; Capella-Peiro , M. ; Carda-Broch , S. ; Esteve-Romero , J. ; Gil-Agust , M. Amitriptyline and nortriptyline serum determination by micellar liquid chromatography . J. Pharmacol. Toxicol. Meth. 2005 , 52 , 323 – 329 .
   Google Scholar
• Louter , A.J.H. ; Bosma , E. ; Schipperen , J.C.A. ; Vreuls , J.J. ; Brinkman , U.A.Th. Automated on-line solid-phase extraction-gas chromatography with nitrogen-phosphorus detection: Determination of benzodiazepines in human plasma . J. Chromatogr. B 1997 , 689 , 35 – 43 .
   PubMed Web of Science ®Google Scholar
• Brooks , M.A. ; Hackman , M.R. ; Weinfeld , R.E. ; Macasieb , T. Determination of clorazepate and its major metabolites in blood and urine by electron capture gas-liquid chromatography. J. Chromatogr. 1977, 135, 123–131.
   PubMed Web of Science ®Google Scholar
• Borrey , D. ; Meyer , E. ; Lambert , W. ; van Calenbergh , S. ; van Peteghem , C. ; De Leenheer , A.P. Sensitive gas chromatographic–mass spectrometric screening of acetylated benzodiazepines . J. Chromatogr. A 2002 , 910 , 105 – 118 .
   Google Scholar
• Sarah , M.R. ; Wille , K.E. ; Maudens , C.H. ; Peteghem , V. ; Lambert , W.E.E. Development of a solid-phase extraction for 13 ‘new’ generation antidepressants and their active metabolites for gas chromatographic–mass spectrometric analysis . J. Chromatogr. A 2005 , 1098 , 19 – 29 .
   Google Scholar
• Qiu , F.H. ; Liu , L. ; Luo , Y. ; Liu , F. ; Lu , Y.Q. Systematic analysis of basic drugs in plasma using X-5 solid-phase extraction GC-FID and GC-MS . Yao Xue Xue Bao. 1996 , 31 ( 4 ), 296 – 299 .
   PubMedGoogle Scholar
• Ulu , S.T. Determination of tianeptine in human plasma using high-performance liquid chromatography with fluorescence detection . J. Chromatogr. B 2006 , 834 , 62 – 67 .
   Google Scholar
• Yoshida , H. ; Hidaka , K. ; Ishida , J. ; Yoshikuni , K. ; Nohta , H. ; Yamaguchi , M. Highly selective and sensitive determination of tricyclic antidepressants in human plasma using high-performance liquid chromatography with post-column tris(2,2′-bipyridyl) ruthenium(iii) chemiluminescence detection . Anal. Chim. Acta 2000 , 413 , 137 – 145 .
   Web of Science ®Google Scholar
• Wilhelm , M. ; Battista , H.J. ; Obendorf , D. HPLC with simultaneous UV and reductive electrochemical detection at the hanging mercury drop electrode: A highly sensitive and selective tool for the determination of benzodiazepines in forensic samples . J. Anal. Toxicol. 2001 , 25 , 250 – 257 .
   PubMed Web of Science ®Google Scholar
• Samanidou , V.F. ; Nika , M.K. ; Papadoyannis , I.N. Development of an HPLC method for the monitoring of tricyclic antidepressants in bio fluids . J. Sepn. Sci. 2007 , 30 , 2391 – 2400 .
   PubMed Web of Science ®Google Scholar
• Ivandini , T.A. ; Sarada , B.V. ; Terashima , C. ; Rao , T.N. ; Tryk , D.A. ; Ishiguro , H. ; Kubota , Y. ; Fujishima , A. Electrochemical detection of tricyclic antidepressant drugs by HPLC using highly boron-doped diamond electrodes . J. Electroanal. Chem. 2002 , 521 , 117 – 126 .
   Web of Science ®Google Scholar
• Van Bocxlaer , J.F. ; Clauwaert , K.M. ; Lambert , W. ; Deforce , D.L. ; van den Eeckhout , E.G. ; De Leenheer , A.P. Liquid chromatography-mass spectrometry in forensic toxicology . Mass Spectrom. Rev. 2000 , 19 , 165 – 214 .
   PubMed Web of Science ®Google Scholar
• Paus , E. ; Jonzier-Perey , M. ; Cochard , N. ; Chin B.E. ; Baumann , P. Chirality in the new generation of antidepressants: Stereoselective snalysis of the enantiomers of mirtazapine, N-demethylmirtazapine, and 8-hydroxymirtazapine by LC-MS . Therap. Drug Monit. 2004 , 26 ( 4 ), 366 – 374 .
   PubMed Web of Science ®Google Scholar
• Juan , H. ; Zhiling , Z. ; Huande , Li. Simultaneous determination of fluoxetine, citalopram, paroxetine, venlafaxine in plasma by high performance liquid chromatography–electrospray ionization mass spectrometry (HPLC–MS/ESI) . J. Chromatog. B 2005 , 820 , 33 – 39 .
   PubMed Web of Science ®Google Scholar
• Titier , K. ; Castaing , N. ; Le-Déodic , M. ; Le-bars , D. ; Moore , N. ; Molimard , M. Quantification of tricyclic antidepressants and monoamine oxidase inhibitors by high-performance liquid chromatography–tandem mass spectrometry in whole blood . J. Anal. Toxic. 2007 , 31 ( 4 ), 200 – 207 .
   PubMed Web of Science ®Google Scholar
• Bugey , A. ; Staub , C. Rapid analysis of benzodiazepines in whole blood by high-performance liquid chromatography: Use of a monolithic column. J. Pharm. Biomed. Anal. 2004, 35 (3), 555–562.
   PubMed Web of Science ®Google Scholar
• Uddin , M.N. ; Samanidou , V.F. ; Papadoyannis , I.N. Development and validation of an HPLC method for the determination of six 1,4-benzodiazepines in pharmaceuticals and human biological fluids . J. Liq. Chromatogr. & Rel. Technol. 2008 , 31 , 1258 – 1282 .
   Web of Science ®Google Scholar
• Hegstad , S. ; Øiestad , E.L. ; Johansen , U. ; Christophersen , A.S. Determination of benzodiazepines in human urine using solid-phase extraction and high-performance liquid chromatography–electrospray ionization tandem mass spectrometry . J. Anal. Toxicol. 2006 , 30 ( 1 ), 31 – 37 .
   PubMed Web of Science ®Google Scholar
• Luo , Y. ; Pan , L. ; Pawliszyn , J. Determination of five benzodiazepines in aqueous solution and biological fluids using solid-phase micro-extraction with carbowax/DVB fiber coating . J. Microcol. Sepn. 1998 , 10 ( 2 ), 193 – 201 .
   Google Scholar
• Uddin , M.N. ; Samanidou , V.F. ; Papadoyannis , I.N. Development and validation of an HPLC method for the determination of benzodiazepines and tricyclic antidepressants in biological fluids after sequential SPE . J. Sepn. Sci. 2008 , 31 , 2358 – 2370 .
   Google Scholar
• CPMP/ICH/281/95, Note for Guidance on Validation of Analytical Procedures: Methodology, ICH Topic Q2B Validation of Analytical Procedures: Methodology, Step 4 (CPMP Adopted December 96) .
   Google Scholar
• Minder , E.I. ; Schaubhut , R. ; Minder , C.E. ; Vonderschmitt , D.J. Identification of drugs in human serum by high performance liquid chromatography with photodiode array detection and a search algorithm for ultraviolet spectra . J. Chromatogr. 1987 , 419 , 135 – 154 .
   PubMed Web of Science ®Google Scholar
• Statistics for Analytical Chemistry , Vol. IV ; Miller , J.C. , Miller , J.N. , Eds.; Horwood E : Chichester , 1986 , 96 .
   Google Scholar