Prominent but Reverse Stereoselectivity in Propranolol Glucuronidation by Human UDP-Glucuronosyltransferases 1A9 and 1A10

No abstract is available for this paper.

• Publication year

  2006

• Venue

  Drug Metabolism And Disposition

• Publication date

  2006-09-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1124/dmd.106.010371PMID 16763014
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Human UDP-Glucuronosyltransferase 1A5: Identification, Expression, and Activity

  2005cited by this paper
• Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily.

  2005cited by this paper
• KINETIC CHARACTERIZATION OF THE 1A SUBFAMILY OF RECOMBINANT HUMAN UDP-GLUCURONOSYLTRANSFERASES

  2005cited by this paper
• BIOSYNTHESIS OF DOBUTAMINE MONOGLUCURONIDES AND GLUCURONIDATION OF DOBUTAMINE BY RECOMBINANT HUMAN UDP-GLUCURONOSYLTRANSFERASES

  2005cited by this paper
• SPECIES- AND DISPOSITION MODEL-DEPENDENT METABOLISM OF RALOXIFENE IN GUT AND LIVER: ROLE OF UGT1A10

  2005cited by this paper
• Stereoselective urinary excretion of S-(-)- and R-(+)-propranolol glucuronide following oral administration of RS-propranolol in Chinese Han subjects.

  2005cited by this paper
• The interactions between the N-terminal and C-terminal domains of the human UDP-glucuronosyltransferases are partly isoform-specific, and may involve both monomers.

  2004cited by this paper
• Glucuronidation and the UDP-glucuronosyltransferases in health and disease.

  2004cited by this paper
• Human udp-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid.

  2004cited by this paper
• Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases.

  2003cited by this paper
• Expression and Characterization of Recombinant Human UDP-glucuronosyltransferases (UGTs)

  2003cited by this paper
• The Human UDP-Glucuronosyltransferases: Structural Aspects and Drug Glucuronidation

  2003cited by this paper
• Genetic multiplicity of the human UDP-glucuronosyltransferases and regulation in the gastrointestinal tract.

  2001cited by this paper
• Cloning of UGT1A9 cDNA from liver tissues and its expression in CHL cells.

  2001cited by this paper
• Human UDP-glucuronosyltransferases: metabolism, expression, and disease.

  2000cited by this paper
• The specificity of glucuronidation of entacapone and tolcapone by recombinant human UDP-glucuronosyltransferases.

  2000cited by this paper
• Bioanalytical Method Validation—A Revisit with a Decade of Progress

  2000cited by this paper
• In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model.

  2000influential reference
• Is the role of the small intestine in first-pass metabolism overemphasized?

  1999cited by this paper
• Structural and functional studies of UDP-glucuronosyltransferases.

  1999cited by this paper
• The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268).

  1998cited by this paper
• Characterization of 1-hydroxypyrene as a novel marker substrate of 3-methylcholanthrene-inducible phenol UDP-glucuronosyltransferase(s).

  1997cited by this paper
• Fundamentals of enzyme kinetics (revised edition)

  1997cited by this paper
• The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence.

  1997cited by this paper
• Fundamentals of Enzyme Kinetics. Revised Edition By Athel Cornish-Bowden. Portland Press, London. 1995. xiii + 343 pp. 17.5 cm × 24.5 cm. ISBN 1-85578-072-0. $29.00.

  1996influential reference
• A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini.

  1992cited by this paper
• Quantitative account of propranolol metabolism in urine of normal man.

  1985cited by this paper
• Isolation, purification, and structure identification of glucuronic acid conjugates of propranolol and alprenolol and their ring-hydroxylated metabolites.

  1984cited by this paper
• Stereoselective disposition and glucuronidation of propranolol in humans.

  1982cited by this paper
• Glucuronidation of propranolol and 4'-hydroxypropranolol. Substrate specificity and stereoselectivity of rat liver microsomal glucuronyltransferases.

  1981cited by this paper
• Pharmacokinetics of propranolol

  1981cited by this paper
• Fundamentals of Enzyme Kinetics

  1979cited by this paper

• Pediatric Beta Blocker Therapy: A Comprehensive Review of Development and Genetic Variation to Guide Precision-Based Therapy in Children, Adolescents, and Young Adults

  2024cites this paper
• Complete Reaction Phenotyping of Propranolol and 4-Hydroxypropranolol with the 19 Enzymes of the Human UGT1 and UGT2 Families

  2022influential citation
• Contribution of UGT Enzymes to Human Drug Metabolism Stereoselectivity: A Case Study of Medetomidine, RO5263397, Propranolol, and Testosterone

  2022cites this paper
• Comparative pharmacodynamic and pharmacokinetic study of MIDD0301 and its (S) enantiomer

  2022cites this paper
• Development and Evaluation of a Physiologically Based Pharmacokinetic Drug-Disease Model of Propranolol for Suggesting Model Informed Dosing in Liver Cirrhosis Patients

  2021cites this paper
• Metabolic profile of the synthetic drug 4,4′-dimethylaminorex in urine by LC–MS-based techniques: selection of the most suitable markers of its intake

  2020cites this paper
• The UDP-Glycosyltransferase (UGT) Superfamily: New Members, New Functions, and Novel Paradigms.

  2019cites this paper
• Importance of the Unstirred Water Layer and Hepatocyte Membrane Integrity In Vitro for Quantification of Intrinsic Metabolic Clearance

  2018cites this paper
• Selectivity in the Efflux of Glucuronides by Human Transporters: MRP4 Is Highly Active toward 4-Methylumbelliferone and 1-Naphthol Glucuronides, while MRP3 Exhibits Stereoselective Propranolol Glucuronide Transport.

  2017cites this paper
• Combined Falling Drop/Open Port Sampling Interface System for Automated Flow Injection Mass Spectrometry.

  2017cites this paper
• Incorporation of the Time-Varying Postprandial Increase in Splanchnic Blood Flow into a PBPK Model to Predict the Effect of Food on the Pharmacokinetics of Orally Administered High-Extraction Drugs

  2017cites this paper
• The regioselective glucuronidation of morphine by dimerized human UGT2B7, 1A1, 1A9 and their allelic variants

  2017cites this paper
• Optimisation of in vitro methodology for drug metabolism studies to improve prediction of hepatic drug clearance

  2016cites this paper
• Predicting substrate selectivity between UGT1A9 and UGT1A10 using molecular modelling and molecular dynamics approach

  2016cites this paper
• Dog UDP-Glucuronosyltransferase Enzymes of Subfamily 1A: Cloning, Expression, and Activity

  2015cites this paper
• Differences in the glucuronidation of bisphenols F and S between two homologous human UGT enzymes, 1A9 and 1A10

  2015cites this paper
• Types of stereoselectivity in drug metabolism: a heuristic approach

  2015cites this paper
• Transcriptional regulation of human UDP-glucuronosyltransferase genes

  2014influential citation
• The dog UGT enzymes of subfamily 1A; cloning, expression and activity

  2014cites this paper
• Substrate selectivity of human intestinal UDP-glucuronosyltransferases (UGTs): in silico and in vitro insights

  2013influential citation
• Activity and Enzyme Kinetics of Human UDP-Glucuronosyltransferases : Studies of Psilocin Glucuronidation and the Effects of Albumin on the Enzyme Kinetic Mechanism

  2013cites this paper
• 3D-QSAR studies on UDP-glucuronosyltransferase 2B7 substrates using the pharmacophore and VolSurf approaches

  2012cites this paper
• International Evaluation of Research and Doctoral Training at the University of Helsinki 2005-2010: RC-Specific Evaluation of MEDCHEMBIO - Medicinal Chemistry and Biochemistry Research Group

  2012cites this paper
• In silico modeling of UDP-glucuronosyltransferase 1A10 substrates using the VolSurf approach.

  2012cites this paper
• UDP‐Glucuronosyltransferases: Pharmacogenetics, Functional Characterization, and Clinical Relevance

  2012cites this paper
• Stereochemical Elements Associated with Drug Metabolism and Toxicity

  2012cites this paper
• Characterizing the effect of UDP-glucuronosyltransferase (UGT) 2B7 and UGT1A9 genetic polymorphisms on enantioselective glucuronidation of flurbiprofen.

  2011cites this paper
• Translational research insights into pharmacokinetic herb-drug interactions.

  2011cites this paper
• Microbial production of phase I and phase II metabolites of propranolol

  2011influential citation
• Diastereomeric Drug Glucuronides: Enzymatic Glucuronidation and Analysis by Capillary Electrophoresis and Liquid Chromatography-Mass Spectrometry

  2011cites this paper
• Understanding Human Drug Conjugating Enzymes; Regio- and Stereoselectivity in Sulfotransferase 1A3 and the UDP-Glucuronosyltransferases

  2011cites this paper
• Pharmacokinetics of Chiral Drugs

  2011cites this paper
• Stereoselective glucuronidation of propafenone and its analogues by human recombinant UGT1A9.

  2010cites this paper
• How Many and Which Amino Acids Are Responsible for the Large Activity Differences between the Highly Homologous UDP-Glucuronosyltransferases (UGT) 1A9 and UGT1A10?

  2010cites this paper
• Fully automated liquid extraction-based surface sampling and ionization using a chip-based robotic nanoelectrospray platform.

  2010cites this paper
• International Evaluation of Research and Doctoral Training at the University of Helsinki 2005-2010: RC-Specific Evaluation of MAC - Modern Analytical Chemistry

  2010cites this paper
• Glucuronidation of racemic O-desmethyltramadol, the active metabolite of tramadol.

  2010cites this paper
• Application of a liquid extraction based sealing surface sampling probe for mass spectrometric analysis of dried blood spots and mouse whole-body thin tissue sections.

  2009cites this paper
• Stereoselective metabolism of propranolol glucuronidation by human UDP-glucuronosyltransferases 2B7 and 1A9.

  2009cites this paper
• Substrate specificity, inhibitors and regulation of human cytochrome P450 2D6 and implications in drug development.

  2009cites this paper
• Glucuronide Isomers: Synthesis, Structural Characterization, and UDP-glucuronosyltransferase Screening

  2009cites this paper
• Stereoselective transport and uptake of propranolol across human intestinal Caco-2 cell monolayers.

  2009cites this paper
• Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development.

  2009cites this paper
• Stereoselectivity in drug metabolism: molecular mechanisms and analytical methods.

  2009cites this paper
• Evaluation of the metabolism of propranolol by linear ion trap technology in mouse, rat, dog, monkey, and human cryopreserved hepatocytes.

  2009cites this paper
• The UDP-glucuronosyltransferases as oligomeric enzymes.

  2008cites this paper
• The Configuration of the 17-Hydroxy Group Variably Influences the Glucuronidation of β-Estradiol and Epiestradiol by Human UDP-Glucuronosyltransferases

  2008influential citation
• Evaluation of HepaRG Cells as an in Vitro Model for Human Drug Metabolism Studies

  2008cites this paper
• Characterization of gastrointestinal drug absorption in cynomolgus monkeys.

  2008cites this paper
• The Biochemistry of Drug Metabolism – An Introduction

  2008cites this paper
• Stereoselective Glucuronidation of Propranolol in Human and Cynomolgus Monkey Liver Microsomes: Role of Human Hepatic UDP-Glucuronosyltransferase Isoforms, UGT1A9, UGT2B4 and UGT2B7

  2008cites this paper
• Stereochemical and steric control of enzymatic glucuronidation : A rational approach for the design of novel Inhibitors for the human UDP-glucuronosyltransferase 2B7

  2008cites this paper
• Variability and Function of Family 1 Uridine-5′-Diphosphate Glucuronosyltransferases (UGT1A)

  2008cites this paper
• Stereoselective Glucuronidation of 5-(4 (cid:1) -Hydroxyphenyl)-5-phenylhydantoin by Human UDP-Glucuronosyltransferase (UGT) 1A1, UGT1A9, and UGT2B15: Effects of UGT-UGT Interactions

  2007cites this paper
• Stereoselective Glucuronidation of 5-(4 (cid:1) -Hydroxyphenyl)-5-phenylhydantoin by Human UDP-Glucuronosyltransferase (UGT) 1A1, UGT1A9, and UGT2B15: Effects of UGT-UGT Interactions

  2007cites this paper
• Stereoselective Glucuronidation of 5-(4 (cid:1) -Hydroxyphenyl)-5-phenylhydantoin by Human UDP-Glucuronosyltransferase (UGT) 1A1, UGT1A9, and UGT2B15: Effects of UGT-UGT Interactions

  2007cites this paper
• Intestinal UGTs as potential modifiers of pharmacokinetics and biological responses to drugs and xenobiotics

  2007cites this paper
• Stereoselective Glucuronidation of 5-(4′-Hydroxyphenyl)-5-phenylhydantoin by Human UDP-Glucuronosyltransferase (UGT) 1A1, UGT1A9, and UGT2B15: Effects of UGT-UGT Interactions

  2007cites this paper
• Lack of Association between Common Polymorphisms in UGT1A9 and Gene Expression and Activity

  2007cites this paper
• Predominant Contribution of UDP-Glucuronosyltransferase 2B7 in the Glucuronidation of Racemic Flurbiprofen in the Human Liver

  2007cites this paper
• Stereoselectivity in drug metabolism

  2007influential citation