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Xenobiotica
the fate of foreign compounds in biological systems
Volume 17, 1987 - Issue 12
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Original Article

Interactions between oxaprozin glucuronide and human serum albumin

D. S. Wells Wyeth Laboratories, P.O. Box 8299, Philadelphia, PA, 19101–8299, USA
,
F. W. Janssen Wyeth Laboratories, P.O. Box 8299, Philadelphia, PA, 19101–8299, USA
&
H. W. Ruelius Johns Hopkins University, School of Medicine, Dept. of Pharmacology, 725 North Wolfe St., Baltimore, MD, 21205, USA
Pages 1437-1449 | Received 01 Jul 1986, Accepted 18 Aug 1986, Published online: 30 Sep 2009

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Glyn Steventon. (2020) Uridine diphosphate glucuronosyltransferase 1A1. Xenobiotica 50:1, pages 64-76.
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E. Skordi, I. D. Wilson, J. C. Lindon & J. K. Nicholson. (2005) Kinetic studies on the intramolecular acyl migration of β-1-O-acyl glucuronides: Application to the glucuronides of (R)- and (S)-ketoprofen, (R)- and (S)-hydroxy-ketoprofen metabolites, and tolmetin by 1H-NMR spectroscopy. Xenobiotica 35:7, pages 715-725.
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Urs A. Boelsterli, Hyman J. Zimmerman & Anke Kretz-Rommel. (1995) Idiosyncratic Liver Toxicity of Nonsteroidal Antiinflammatory Drugs: Molecular Mechanisms and Pathology. Critical Reviews in Toxicology 25:3, pages 207-235.
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J. C. Ojingwa, H. Spahn-Langguth & L. Z. Benet. (1994) Irreversible binding of tolmetin to macromolecules via its glucuronide: Binding to blood constituents, tissue homogenates and subcellular fractions in vitro. Xenobiotica 24:6, pages 495-506.
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P. C. Smith & J. H. Liu. (1993) Covalent binding of suprofen acyl glucuronide to albumin in vitro. Xenobiotica 23:4, pages 337-348.
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Hildegard Spahn Langguth & Leslie Z. Benet. (1992) Acyl Glucuronides Revisited: Is the Glucuronidation Proces a Toxification as Well as a Detoxification Mechanism?. Drug Metabolism Reviews 24:1, pages 5-47.
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Gerard Siest, Sylvie Fournel-Gigleux, Jacques Magdalou & Denyse Bagrel. (1989) Cellular and Molecular Aspects of Udp-Glucuronosyltransferases. Drug Metabolism Reviews 20:2-4, pages 721-731.
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Articles from other publishers (33)

Giovanna De Simone, Alessandra di Masi & Paolo Ascenzi. (2021) Serum Albumin: A Multifaced Enzyme. International Journal of Molecular Sciences 22:18, pages 10086.
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Eszter Fliszár-Nyúl, Zelma Faisal, Violetta Mohos, Diána Derdák, Beáta Lemli, Tamás Kálai, Cecília Sár, Balázs Z. Zsidó, Csaba Hetényi, Ádám I. Horváth, Zsuzsanna Helyes, Ruth Deme, Dóra Bogdán, Andrea Czompa, Péter Mátyus & Miklós Poór. (2021) Interaction of SZV 1287, a novel oxime analgesic drug candidate, and its metabolites with serum albumin. Journal of Molecular Liquids 333, pages 115945.
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Howard Horng & Leslie Z. Benet. (2013) The Nonenzymatic Reactivity of the Acyl-Linked Metabolites of Mefenamic Acid toward Amino and Thiol Functional Group Bionucleophiles. Drug Metabolism and Disposition 41:11, pages 1923-1933.
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Howard Horng, Hilde Spahn-Langguth & Leslie Z. Benet. 2013. Drug-Induced Liver Disease. Drug-Induced Liver Disease 35 70 .
Alexander V. LyubimovRobert S. Foti, Dan A. Rock, Larry C. Wienkers & Jan L. Wahlstrom. 2011. Encyclopedia of Drug Metabolism and Interactions. Encyclopedia of Drug Metabolism and Interactions 1 68 .
Yoshio Tanaka & Akira Suzuki. (1994) Enzymatic Hydrolysis of Zenarestat 1- O -Acylglucuronide . Journal of Pharmacy and Pharmacology 46:3, pages 235-239.
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Benedetta C. Sallustio. 2008. 57 86 .
Chunze Li, Mobolaji O. Olurinde, Laura M. Hodges, Mark P. Grillo & Leslie Z. Benet. (2003) COVALENT BINDING OF 2-PHENYLPROPIONYL- S -ACYL-COA THIOESTER TO TISSUE PROTEINS IN VITRO . Drug Metabolism and Disposition 31:6, pages 727-730.
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T. Ohkawa, R. Norikura & T. Yoshikawa. (2003) Rapid LC-TOFMS method for identification of binding sites of covalent acylglucuronide–albumin complexes. Journal of Pharmaceutical and Biomedical Analysis 31:6, pages 1167-1176.
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Maria Shipkova, Victor William Armstrong, Michael Oellerich & Eberhard Wieland. (2003) Acyl Glucuronide Drug Metabolites: Toxicological and Analytical Implications. Therapeutic Drug Monitoring 25:1, pages 1-16.
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K. D. Rainsford, H. Omar, A. Ashraf, A. T. Hewson, R. A. D. Bunning, R. Rishiraj, P. Shepherd & R. W. Seabrook. (2002) Recent pharmacodynamic and pharmacokinetic findings on oxaprozin. InflammoPharmacology 10:3, pages 185-239.
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H�l�ne Georges, Nathalie Presle, Thierry Buronfosse, Sylvie Fournel-Gigleux, Patrick Netter, Jacques Magdalou & Fran�oise Lapicque. (2000) In vitro stereoselective degradation of carprofen glucuronide by human serum albumin. Characterization of sites and reactive amino acids. Chirality 12:2, pages 53-62.
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Hélène Georges, Isabelle Jarecki, Patrick Netter, Jacques Magdalou & Françoise Lapicque. (1999) Glycation of human serum albumin by acylglucuronides of nonsteroidal anti-inflammatory drugs of the series of phenylpropionates. Life Sciences 65:12, pages PL151-PL156.
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Masahiro Iwaki, Taro Ogiso, Shinako Inagawa & Kazuaki Kakehi. (1999) In Vitro Regioselective Stability of β‐1‐O‐ and 2‐O‐Acyl Glucuronides of Naproxen and Their Covalent Binding to Human Serum Albumin. Journal of Pharmaceutical Sciences 88:1, pages 52-57.
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Jana Oravcova´, Barbara Bo¨hs & Wolfgang Lindner. (1996) Drug-protein binding studies new trends in analytical and experimental methodology. Journal of Chromatography B: Biomedical Sciences and Applications 677:1, pages 1-28.
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Hildegard Spahn-Langguth, Monika Dahms & Andreas Hermening. 1996. Biological Reactive Intermediates V. Biological Reactive Intermediates V 313 328 .
Alfred Bischer, Parnian Zia-Amirhosseini, Masahiro Iwaki, Antony F. McDonagh & Leslie Z. Benet. (1995) Stereoselective binding properties of naproxen glucuronide diastereomers to proteins. Journal of Pharmacokinetics and Biopharmaceutics 23:4, pages 379-395.
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Peter J. Hayball. (2004) Formation and reactivity of acyl glucuronides: The influence of chirality. Chirality 7:1, pages 1-9.
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Nathalie Dubois, Françoise Lapicque, Jacques Magdalou, Michel Abiteboul & Patrick Netter. (1994) Stereoselective binding of the glucuronide of ketoprofen enantiomers to human serum albumin. Biochemical Pharmacology 48:9, pages 1693-1699.
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Adrienne M. Williams & Ronald G. Dickinson. (1994) Studies on the reactivity of acyl glucuronides—VI. Biochemical Pharmacology 47:3, pages 457-467.
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Joseph C. Ojingwa, Hildegard Spahn-Langguth & Leslie Z. Benet. (1994) Reversible binding of tolmetin, zomepirac, and their glucuronide conjugates to human serum albumin and plasma. Journal of Pharmacokinetics and Biopharmaceutics 22:1, pages 19-40.
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Parnian Zia-Amirhosseini, Hildegard Spahn-Langguth & Leslie Z. Benet. 1994. 385 397 .
C. Fenselau. 1994. Conjugation—Deconjugation Reactions in Drug Metabolism and Toxicity. Conjugation—Deconjugation Reactions in Drug Metabolism and Toxicity 367 389 .
Haiyung Cheng & William J. Jusko. (2006) Pharmacokinetics of reversible metabolic systems. Biopharmaceutics & Drug Disposition 14:9, pages 721-766.
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N. Grubb, A. Weil & J. Caldwell. (1993) Studies on the in vitro reactivity of clofibryl and fenofibryl glucuronides. Biochemical Pharmacology 46:3, pages 357-364.
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Philip C. Smith & Wang Chyoan. (1992) Nonenzymic glycation of albumin by acyl glucuronides in vitro comparison of reactions with reducing sugars. Biochemical Pharmacology 44:8, pages 1661-1668.
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Peter J. Hayball, Roger L. Nation & Felix Bochner. (1992) Stereoselective interactions of ketoprofen glucuronides with human plasma protein and serum albumin. Biochemical Pharmacology 44:2, pages 291-299.
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J. Fevery & J. Gonzalez-Gallego. 1992. Hepatobiliary Diseases. Hepatobiliary Diseases 181 199 .
Ronald G. Dickinson & Andrew R. King. (1991) Studies on the reactivity of acyl glucuronides—II. Biochemical Pharmacology 42:12, pages 2301-2306.
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Benedetta C. Sallustio, Kathleen M. Knights, Benjamin J. Roberts & Rudolf Zacest. (1991) In vivo covalent binding of clofibric acid to human plasma proteins and rat liver proteins. Biochemical Pharmacology 42:7, pages 1421-1425.
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Julia A. Watt & Ronald G. Dickinson. (1990) Reactivity of diflunisal acyl glucuronide in human and rat plasma and albumin solutions. Biochemical Pharmacology 39:6, pages 1067-1075.
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Iwakawa Seigo, Hildegard Spahn, Leslie Z. Benet & Emil T. Lin. (1990) Stereoselective binding of the glucuronide conjugates of carprofen enantiomers to human serum albumin. Biochemical Pharmacology 39:5, pages 949-953.
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Johan Fevery, Florent Vanstapel & Norbert Blanckaert. (1989) Bile pigment metabolism. Baillière's Clinical Gastroenterology 3:2, pages 283-312.
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