Identification of a Novel Glutathione Conjugate of Flutamide in Incubations with Human Liver Microsomes

No abstract is available for this paper.

• Publication year

  2007

• Venue

  Drug Metabolism And Disposition

• Publication date

  2007-07-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1124/dmd.107.014860PMID 17403914
• 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.

• A semiquantitative method for the determination of reactive metabolite conjugate levels in vitro utilizing liquid chromatography-tandem mass spectrometry and novel quaternary ammonium glutathione analogues.

  2006cited by this paper
• FLUTAMIDE METABOLISM IN FOUR DIFFERENT SPECIES IN VITRO AND IDENTIFICATION OF FLUTAMIDE METABOLITES IN HUMAN PATIENT URINE BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY/TANDEM MASS SPECTROMETRY

  2006influential reference
• Metabolism and hepatic toxicity of flutamide in cytochrome P450 1A2 knockout SV129 mice

  2006cited by this paper
• DETECTION OF A NEW N-OXIDIZED METABOLITE OF FLUTAMIDE, N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]HYDROXYLAMINE, IN HUMAN LIVER MICROSOMES AND URINE OF PROSTATE CANCER PATIENTS

  2006cited by this paper
• Fatal liver complications with flutamide.

  2006cited by this paper
• Induction of liver cytochrome P450 1A2 expression by flutamide in rats

  2005cited by this paper
• The pharmacokinetics of flutamide and its major metabolites after a single oral dose and during chronic treatment

  2004influential reference
• Addressing the metabolic activation potential of new leads in drug discovery: a case study using ion trap mass spectrometry and tritium labeling techniques.

  2003cited by this paper
• Cytotoxicity of flutamide and 2-hydroxyflutamide and their effects on CYP1A2 mRNA in primary rat hepatocytes.

  2002cited by this paper
• Hydroxypropyl-beta-cyclodextrin-flutamide inclusion complex. II. Oral and intravenous pharmacokinetics of flutamide in the rat.

  2002cited by this paper
• Hypochlorite-induced damage to DNA, RNA, and polynucleotides: formation of chloramines and nitrogen-centered radicals.

  2002cited by this paper
• In Vitro Effects of Fluoroquinolone Anti-bacterial Agents on Flutamide Metabolism in Human Liver Microsomes

  2001cited by this paper
• Combined androgen blockade with nonsteroidal antiandrogens for advanced prostate cancer: a systematic review.

  2001cited by this paper
• Improvement of Flutamide-induced hepatotoxicity by Ursodeoxycholic acid in male rats.

  1999cited by this paper
• Frequency of flutamide induced hepatotoxicity in patients with prostate carcinoma

  1999cited by this paper
• [Flutamide-induced hepatic disorder and serum concentrations of flutamide and its metabolites in patients with prostate cancer].

  1999cited by this paper
• Additional pathways of S-conjugate formation during interaction of 4-nitrosophenetole with glutathione.

  1998cited by this paper
• Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2.

  1997cited by this paper
• Flutamide hepatotoxicity.

  1996cited by this paper
• Toxicity of the antiandrogen flutamide in isolated rat hepatocytes.

  1994cited by this paper
• Metabolic activation of the nitroaromatic antiandrogen flutamide by rat and human cytochromes P-450, including forms belonging to the 3A and 1A subfamilies.

  1993cited by this paper
• The pecking order of free radicals and antioxidants: lipid peroxidation, alpha-tocopherol, and ascorbate.

  1993cited by this paper
• Antiandrogenic drugs

  1993cited by this paper
• Nephrotoxicity of the 1:1 acrolein-glutathione adduct in the rat.

  1992cited by this paper
• Simultaneous liver and lung toxicity related to the nonsteroidal antiandrogen nilutamide (Anandron): a case report.

  1992cited by this paper
• Flutamide. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in advanced prostatic cancer.

  1989cited by this paper
• Flutamide and hepatitis.

  1989cited by this paper
• The chemistry of sulfenamides

  1989cited by this paper
• Reaction of mutagenic phenacetin metabolites with glutathione and DNA. Possible implications for toxicity.

  1984influential reference
• γ‐Glutamyl Transpeptidase: Sidedness of Its Active Site on Renal Brush‐Border Membrane

  1978cited by this paper
• Gamma-glutamyl transpeptidase: sidedness of its active site on renal brush-border membrane.

  1978cited by this paper
• Glutathione and related gamma-glutamyl compounds: biosynthesis and utilization.

  1976cited by this paper
• Disposition of a New, Nonsteroid, Antiandrogen, α,α,α-Trifluoro-2-methyl-4′-nitro-m-propionotoluidide (Flutamide), in Men Following a single Oral 200 mg Dose

  1975cited by this paper
• Disposition of a new, nonsteroid, antiandrogen, alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-m-propionotoluidide (Flutamide), in men following a single oral 200 mg dose.

  1975cited by this paper
• γ-Glutamyl-Transpeptidase

  1973cited by this paper

• Formation of potentially toxic metabolites of drugs in reactions catalyzed by human drug-metabolizing enzymes

  2024cites this paper
• Potentiation of flutamide-induced hepatotoxicity in mice by Xian-Ling-Gu-Bao through induction of CYP1A2.

  2021cites this paper
• Human Family 1–4 cytochrome P450 enzymes involved in the metabolic activation of xenobiotic and physiological chemicals: an update

  2021cites this paper
• Evaluation of covalent binding of flutamide and its risk assessment using 19F-NMR

  2020cites this paper
• Selenium and Glutathione-Depleted Rats as a Sensitive Animal Model to Predict Drug-Induced Liver Injury in Humans

  2019cites this paper
• Cell-based assay using glutathione-depleted HepaRG and HepG2 human liver cells for predicting drug-induced liver injury.

  2018cites this paper
• Biomimetic trapping cocktail to screen reactive metabolites: use of an amino acid and DNA motif mixture as light/heavy isotope pairs differing in mass shift

  2018cites this paper
• Flutamide Induces Hepatic Cell Death and Mitochondrial Dysfunction via Inhibition of Nrf2-Mediated Heme Oxygenase-1

  2018cites this paper
• Redox Signaling by Reactive Electrophiles and Oxidants.

  2018cites this paper
• TAMH: A Useful In Vitro Model for Assessing Hepatotoxic Mechanisms

  2016cites this paper
• The antiandrogen flutamide is a novel aryl hydrocarbon receptor ligand that disrupts bile acid homeostasis in mice through induction of Abcc4.

  2016cites this paper
• Formation of A Novel Purine Metabolite through CYP3A4 Bioactivation and Glutathione Conjugation

  2016cites this paper
• Characterization of A α C-serum albumin adducts 2-Amino-9 H-pyrido [ 2 , 3-b ] indole ( A α C ) Adducts and Thiol Oxidation of Serum Albumin as Potential Biomarkers of Tobacco Smoke

  2015cites this paper
• 2-Amino-9H-pyrido[2,3-b]indole (AαC) Adducts and Thiol Oxidation of Serum Albumin as Potential Biomarkers of Tobacco Smoke*

  2015cites this paper
• Post-acquisition analysis of untargeted accurate mass quadrupole time-of-flight MS(E) data for multiple collision-induced neutral losses and fragment ions of glutathione conjugates.

  2014cites this paper
• Should the incorporation of structural alerts be restricted in drug design? An analysis of structure-toxicity trends with aniline-based drugs.

  2014cites this paper
• Flutamide-Induced Cytotoxicity and Oxidative Stress in an In Vitro Rat Hepatocyte System

  2014cites this paper
• Evaluation of Drug-Induced Liver Injury in an In Vitro Oxidative Stress Inflammation System

  2014cites this paper
• Idiosyncratic Drug Reactions

  2012cites this paper
• Covalent Drug–Protein Adducts: An Exploration of Their Role in Drug‐Induced Liver and General Organ Toxicity

  2012cites this paper
• Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: a perspective based on the critical examination of trends in the top 200 drugs marketed in the United States.

  2011cites this paper
• Protocols of in vitro protein covalent binding studies in liver.

  2011cites this paper
• Combination of GSH Trapping and Time-Dependent Inhibition Assays as a Predictive Method of Drugs Generating Highly Reactive Metabolites

  2011cites this paper
• Mechanisms of Drug‐induced Liver Injury

  2011cites this paper
• Flutamide-induced hepatotoxicity: a case report.

  2011cites this paper
• Application of diffusion-edited NMR spectroscopy for the structural characterization of drug metabolites in mixtures.

  2010cites this paper
• Microscopic Evaluation of the Role of Yeast Extract in Flutamide Hepatotoxicity

  2010cites this paper
• Microbial metabolism. Part 11. Metabolites of flutamide.

  2010cites this paper
• Identification of Finasteride Metabolites in Human Bile and Urine by High-Performance Liquid Chromatography/Tandem Mass Spectrometry

  2009cites this paper
• Metabolic Activation of Benzodiazepines by CYP 3 A 4 □ S

  2009cites this paper
• Screening strategy for the rapid detection of in vitro generated glutathione conjugates using high-performance liquid chromatography and low-resolution mass spectrometry in combination with LightSight software for data processing.

  2009cites this paper
• Microsoft Word-26784145-file00

  2009cites this paper
• Metabolic Activation of Benzodiazepines by CYP3A4

  2009cites this paper
• Identification of metabolites of adonifoline, a hepatotoxic pyrrolizidine alkaloid, by liquid chromatography/tandem and high-resolution mass spectrometry.

  2009cites this paper
• Drug-induced hepatotoxicity test using gamma-glutamylcysteine synthetase knockdown rat.

  2009cites this paper
• Topological polar surface area defines substrate transport by multidrug resistance associated protein 1 (MRP1/ABCC1).

  2009cites this paper
• Underlying mitochondrial dysfunction triggers flutamide-induced oxidative liver injury in a mouse model of idiosyncratic drug toxicity.

  2009cites this paper
• Role of Enzymatic N-Hydroxylation and Reduction in Flutamide Metabolite-Induced Liver Toxicity

  2009cites this paper
• Comparison of in vitro bioactivation of flutamide and its cyano analogue: evidence for reductive activation by human NADPH:cytochrome P450 reductase.

  2008cites this paper
• Bioactivation of Flutamide Metabolites by Human Liver Microsomes

  2008influential citation
• Covalent Binding and Tissue Distribution/Retention Assessment of Drugs Associated with Idiosyncratic Drug Toxicity

  2008cites this paper
• Transport, metabolism, and hepatotoxicity of flutamide, drug-drug interaction with acetaminophen involving phase I and phase II metabolites.

  2007influential citation
• Comparison of the cytotoxicity of the nitroaromatic drug flutamide to its cyano analogue in the hepatocyte cell line TAMH: evidence for complex I inhibition and mitochondrial dysfunction using toxicogenomic screening.

  2007cites this paper