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Xenobiotica
the fate of foreign compounds in biological systems
Volume 21, 1991 - Issue 10
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Research Article

N+-Glucuronidation of aliphatic tertiary amines, a general phenomenon in the metabolism of H1-antihistamines in humans

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Pages 1281-1288 | Received 29 Oct 1990, Accepted 16 May 1991, Published online: 22 Sep 2008

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Danyi Lu, Dong Dong & Baojian Wu. (2018) Highly selective N-glucuronidation of four piperazine-containing drugs by UDP-glucuronosyltransferase 2B10. Expert Opinion on Drug Metabolism & Toxicology 14:9, pages 989-998.
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Jayaprakasam Bolleddula, Kevin DeMent, James P. Driscoll, Philip Worboys, Patrick J. Brassil & David L. Bourdet. (2014) Biotransformation and bioactivation reactions of alicyclic amines in drug molecules. Drug Metabolism Reviews 46:3, pages 379-419.
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Sanna Kaivosaari, Moshe Finel & Mikko Koskinen. (2011) N-glucuronidation of drugs and other xenobiotics by human and animal UDP-glucuronosyltransferases. Xenobiotica 41:8, pages 652-669.
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Shu-Feng Zhou, Jun-Ping Liu & Balram Chowbay. (2009) Polymorphism of human cytochrome P450 enzymes and its clinical impact. Drug Metabolism Reviews 41:2, pages 89-295.
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L. MARTINEZ, M. T. SERAFINI, M. J. PRETEL, A. GARCIA-SORET, T. MORAGON & S. PUIG. (1999) Absorption, distribution, metabolism and excretion of cizolirtine, a new analgesic compound, in rat and dog. Xenobiotica 29:8, pages 859-871.
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H. Luo, E. M. Hawes, G. McKay, E. D. Korchinski & K. K. Midha. (1995) N+ -Glucuronidation of aliphatic tertiary amines in human: antidepressant versus antipsychotic drugs. Xenobiotica 25:3, pages 291-301.
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Nicholas A. Meanwell. (2023) The pyridazine heterocycle in molecular recognition and drug discovery. Medicinal Chemistry Research.
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Danyi Lu, Qian Xie & Baojian Wu. (2017) N-glucuronidation catalyzed by UGT1A4 and UGT2B10 in human liver microsomes: Assay optimization and substrate identification. Journal of Pharmaceutical and Biomedical Analysis 145, pages 692-703.
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Keith K. Burkhart, Darrell Abernethy & David Jackson. (2015) Data Mining FAERS to Analyze Molecular Targets of Drugs Highly Associated with Stevens-Johnson Syndrome. Journal of Medical Toxicology 11:2, pages 265-273.
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Line Rørbæk Olsen, Charlotte Gabel-Jensen, Peter Aadal Nielsen, Steen Honoré Hansen & Lassina Badolo. (2014) Identification of a Functional Homolog of the Mammalian CYP3A4 in Locusts. Drug Metabolism and Disposition 42:7, pages 1153-1162.
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Jia Liu. 2014. Handbook of Metabolic Pathways of Xenobiotics. Handbook of Metabolic Pathways of Xenobiotics 1 4 .
Jane W.A. Vella-Brincat, Evan J. Begg, Berit P. Jensen, Paul K.L. Chin, Rebecca L. Roberts, Mary Fairhall, Sandy (A.D.) Macleod & Kate Reid. (2012) The Pharmacokinetics and Pharmacogenetics of the Antiemetic Cyclizine in Palliative Care Patients. Journal of Pain and Symptom Management 43:3, pages 540-548.
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Dorothee Fischer & Ursula Breyer-Pfaff. (1995) Comparison of Procedures for Measuring the Quaternary N -Glucuronides of Amitriptyline and Diphenhydramine in Human Urine with and without Hydrolysis . Journal of Pharmacy and Pharmacology 47:6, pages 534-538.
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Berit Packert Jensen, Jane Winifred Ann Vella-Brincat & Evan James Begg. (2011) Quantification of cyclizine and norcyclizine in human plasma by liquid chromatography–tandem mass spectrometry (LC–MS/MS). Journal of Chromatography B 879:9-10, pages 605-609.
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Wilna J. Moree, Bin-Feng Li, Said Zamani-Kord, Jinghua Yu, Timothy Coon, Charles Huang, Dragan Marinkovic, Fabio C. Tucci, Siobhan Malany, Margaret J. Bradbury, Lisa M. Hernandez, Jianyun Wen, Hua Wang, Samuel R.J. Hoare, Robert E. Petroski, Kayvon Jalali, Chun Yang, Aida Sacaan, Ajay Madan, Paul D. Crowe & Graham Beaton. (2010) Identification of a novel selective H1-antihistamine with optimized pharmacokinetic properties for clinical evaluation in the treatment of insomnia. Bioorganic & Medicinal Chemistry Letters 20:19, pages 5874-5878.
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Shu-Feng Zhou. (2009) Polymorphism of Human Cytochrome P450 2D6 and Its Clinical Significance. Clinical Pharmacokinetics 48:12, pages 761-804.
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Bernard Testa & Stefanie D. Krämer. (2008) The Biochemistry of Drug Metabolism – An Introduction. Chemistry & Biodiversity 5:11, pages 2171-2336.
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Kenichiro Ogura, Yuko Ishikawa, Teppei Kaku, Takahito Nishiyama, Tomokazu Ohnuma, Kei Muro & Akira Hiratsuka. (2006) Quaternary ammonium-linked glucuronidation of trans-4-hydroxytamoxifen, an active metabolite of tamoxifen, by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochemical Pharmacology 71:9, pages 1358-1369.
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Teppei Kaku, Kenichiro Ogura, Takahito Nishiyama, Tomokazu Ohnuma, Kei Muro & Akira Hiratsuka. (2004) Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochemical Pharmacology 67:11, pages 2093-2102.
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Donald J. AbrahamBernard Testa & William Soine. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 431 498 .
Gary S. Richardson, Timothy A. Roehrs, Leon Rosenthal, Gail Koshorek & Thomas Roth. (2002) Tolerance to Daytime Sedative Effects of H1 Antihistamines. Journal of Clinical Psychopharmacology 22:5, pages 511-515.
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I Kowalczyk, E.M Hawes & G McKay. (2000) Stability and enzymatic hydrolysis of quaternary ammonium-linked glucuronide metabolites of drugs with an aliphatic tertiary amine-implications for analysis. Journal of Pharmaceutical and Biomedical Analysis 22:5, pages 803-811.
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D. Fischer & U. Breyer-Pfaff. (1997) Variability of diphenhydramine N-glucuronidation in healthy subjects. European Journal of Drug Metabolism and Pharmacokinetics 22:2, pages 151-154.
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R.B. Walker & I. Kanfer. (1996) Pharmacokinetics of cyclizine following intravenous administration to human volunteers. European Journal of Pharmaceutical Sciences 4:5, pages 301-306.
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George R. Tonn, Frank S. Abbott, Dan W. Rurak & James E. Axelson. (1995) Simultaneous analysis of diphenylmethoxyacetic acid, a metabolite of diphenhydramine, and its deuterium-labeled stable isotope analog in ovine plasma and urine. Journal of Chromatography B: Biomedical Sciences and Applications 663:1, pages 67-81.
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H. Luo, G. McKay & K. K. Midha. (1994) Identification of clozapineN+-glucuronide in the urine of patients treated with clozapine using electrospray mass spectrometry. Biological Mass Spectrometry 23:3, pages 147-148.
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Margitta Albinus, Gudrun Amschler, Uwe Amschler, Erwin von Angerer, Wolfgang Barthel, Andrea Bauer, Kurt Bauer, Jürgen Beckmann, Winfried Beil, Jürgen Beitz, Petra Berscht, Thorsten Beyrich, Katja Binder, Roswitha Böhme, Hans-Hubertus Borchert, Franz Bracher, Helmut Bräunlich, Kerstin Brinkmann, Franz von Bruchhausen, Kay Brune, Axel Büge, Wolfram Christ, Monika Cimbollek, Rolf Daniels, Gerd Dannhardt, Hans-Jürgen Duchstein, Siegfried Ebel, Kurt Eger, Peter Emig, Thomas Erker, Maria S. Fernandez-Alfonso, August Wilhelm Frahm, Margarete Frahm, Klaus-Jürgen Freundt, Detlef Geffken, Ulrich Geis, Erika Glusa, Berthold Göber, Jochen Gödicke, Margarete Goppelt-Strübe, Wilhelm Gössling, Annette Graul, Sibylle Greiner, Adolf Grisk, Michael Grosam, Markus von Gruchalla, Michael Gütschow, Axel Haberkorn, Eberhard Hackenthal, Annette Häfner, Boris Haluszczynski, Achim Harder, Sabine Hartmann, Susanne Hartmann, Dieter Heber, Gerhard Heinemeyer, Andreas Hensel, Sibylle Hoedt-Schmidt, Hermann Hoffmann, Ute Hoffmann-Schollmayer, Ulrike Holzgrabe, Martin Hug, Wolfgang Ibrom, Elisabeth Inkmann, Jens Jürgens, Brigitte Kaiser, Dieter-Abbo Kalbhen, Nasser Khudeir, Werner Kiefer, Doris Kleinsorge, Christoph Klett, Stephanie Klett, Martin Klingmüller, H.-P. Klöcking, Gerd Kobal, Axel Kramer, Mareta Kreher, Gottfried Kreutz, Reinhard Kroker, Dorothea Landsiedel-Maier, Jochen Lehmann, Marion Sylvia Lehner, Stefan Leiner, Hans Löwe, Johannes Mann, Detlef Manns, Wolfgang Matthiessen, Andreas Maurer, Wolfgang Meindl, Klaus Menges, Paul Messinger, Hans-Jürgen Mest, Frank Peter Meyer, J. Mollière, Rudolf Morgenstern, Wolfgang Morick, Joachim Mössner, Christa Müller, Daniel Müller, Klaus Müller, Walter Müller, Alexander Mülsch, Tilo Netzer, Michael Neugebauer, Ulf Niemeyer, Peter Nuhn, Bernd Nürnberg, Joachim Oertel, Michael Oettel, Hartmut Oßwald, Robert Ott, Tilmann Ott, Thomas Otzen, Peter Pachaly, Helmut Pelzer, Karl-Uwe Petersen, Martina Pickert, Andreas Pies, Klaus Pietrzik, Detlef Preiss, Helmut Priewer, Olaf Queckenberg, Eberhard Reimann, Jörg Remien, Rainer Rettig, Andreas Reymann, Joachim Richter, Hans Rommelspacher, Ulrich Rose, Gerhard Rücker, Klaus Schaefer, Helmut Schlager, Werner Schleicher, Hildegard Schleinitz, Wolfgang Schlichter, Helmut Schmidhammer, Gerhard Schmidt, Timo Schmidt, Johannes Schräder, Thomas Schulz, Gert Schulze, Peter Schwanz, Helmut Schwilden, Monika Serke, Gisela Skopp, Marcus Spohn, Ralf Stahlmann, Johannes-Peter Stasch, Christian Steffen, Jürgen Steinmeyer, Karl-Heinz Surborg, Ulf Sürig, Istvan Szelenyi, Reinhard Troschütz, Michael Verborg, Eugen J. Verspohl, Franz-Josef Volk, Heinz Walther, Horst Weber, Judith Wede, Martin Wenzel, Marion Weyandt-Spangenberg, Sandra Wich, Hilke Winterhoff, Reinhold Wintersteiger, Frauke Woltmann, Diaa Youssef & A. Ziegler. 1994. Hagers Handbuch der Pharmazeutischen Praxis. Hagers Handbuch der Pharmazeutischen Praxis 1 467 .
H. Luo, E.M. Hawes, G. McKay & K.K. Midha. (1992) Synthesis and Characterization of Quaternary Ammonium-Linked Glucuronide Metabolites of Drugs with an Aliphatic Tertiary Amine Group. Journal of Pharmaceutical Sciences 81:11, pages 1079-1083.
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