Home Amines 16110-10-4
16110-10-4,MFCD03094680
Catalog No.:AA00AKJ3

16110-10-4 | acetaminophen glucuronide

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Technical Information
Catalog Number:
AA00AKJ3
Chemical Name:
acetaminophen glucuronide
CAS Number:
16110-10-4
Molecular Formula:
C14H17NO8
Molecular Weight:
327.2867
MDL Number:
MFCD03094680
SMILES:
CC(=O)Nc1ccc(cc1)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O
Properties
Computed Properties
 
Complexity:
437  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
4  
XLogP3:
-0.8  

Literature

Title: Modulation of O-GlcNAc Levels in the Liver Impacts Acetaminophen-Induced Liver Injury by Affecting Protein Adduct Formation and Glutathione Synthesis.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20180401

Title: A cellular model to study drug-induced liver injury in nonalcoholic fatty liver disease: Application to acetaminophen.

Journal: Toxicology and applied pharmacology 20160201

Title: Simultaneous LC-MS/MS quantitation of acetaminophen and its glucuronide and sulfate metabolites in human dried blood spot samples collected by subjects in a pilot clinical study.

Journal: Bioanalysis 20120601

Title: Investigating paracetamol pharmacokinetics using venous and capillary blood and saliva sampling.

Journal: The Journal of pharmacy and pharmacology 20120501

Title: Simultaneous quantitative determination of paracetamol and its glucuronide conjugate in human plasma and urine by liquid chromatography coupled to electrospray tandem mass spectrometry: application to a clinical pharmacokinetic study.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120415

Title: UDP-glucuronosyltransferase expression in mouse liver is increased in obesity- and fasting-induced steatosis.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120201

Title: Imitation of drug metabolism in human liver and cytotoxicity assay using a microfluidic device coupled to mass spectrometric detection.

Journal: Lab on a chip 20120107

Title: Pharmacokinetics and ocular disposition of paracetamol and paracetamol glucuronide in rabbits with diabetes mellitus induced by alloxan.

Journal: Pharmacological reports : PR 20120101

Title: The impact of Caesarean delivery on paracetamol and ketorolac pharmacokinetics: a paired analysis.

Journal: Journal of biomedicine & biotechnology 20120101

Title: Postprandial and fasting hepatic glucose fluxes in long-standing type 1 diabetes.

Journal: Diabetes 20110601

Title: Effects of imatinib mesylate on the pharmacokinetics of paracetamol (acetaminophen) in Korean patients with chronic myelogenous leukaemia.

Journal: British journal of clinical pharmacology 20110201

Title: Acetaminophen pharmacokinetics in children with nonalcoholic fatty liver disease.

Journal: Journal of pediatric gastroenterology and nutrition 20110201

Title: Pharmacokinetics of intravenous paracetamol in elderly patients.

Journal: Clinical pharmacokinetics 20110201

Title: Comparison of the pharmacokinetics of paracetamol from two generic products in patients after total gastric resection.

Journal: Pharmacological reports : PR 20110101

Title: Evaluating human liver reserve function by measuring serum concentrations of phenacetin and its metabolites.

Journal: Journal of digestive diseases 20101201

Title: Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol.

Journal: International journal of pharmaceutics 20100104

Title: The effect of transcatheter arterial chemoembolization on phase II drug metabolism enzymes in patients with hepatocellular carcinoma.

Journal: Cancer chemotherapy and pharmacology 20100101

Title: Does rapid metabolism ensure negligible risk from bisphenol A?

Journal: Environmental health perspectives 20091101

Title: In vivo glucuronidation activity of drugs in neonates: extensive interindividual variability despite their young age.

Journal: Therapeutic drug monitoring 20090801

Title: Studies of acetaminophen and metabolites in urine and their correlations with toxicity using metabolomics.

Journal: Drug metabolism letters 20090801

Title: Additional evidence that transaldolase exchange, isotope discrimination during the triose-isomerase reaction, or both occur in humans: effects of type 2 diabetes.

Journal: Diabetes 20090701

Title: Simultaneous RP-HPLC determination of sotalol, metoprolol, alpha-hydroxymetoprolol, paracetamol and its glucuronide and sulfate metabolites in human urine.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20090601

Title: Effect of repeated administration with subtoxic doses of acetaminophen to rats on enterohepatic recirculation of a subsequent toxic dose.

Journal: Biochemical pharmacology 20090515

Title: Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20090501

Title: Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation.

Journal: Clinical and experimental pharmacology & physiology 20090101

Title: Effect of the acute phase response induced by endotoxin administration on the expression and activity of UGT isoforms in rats.

Journal: Drug metabolism letters 20081201

Title: Prandial insulin and the systemic appearance of meal-derived glucose in people with type 1 diabetes.

Journal: Diabetes care 20081101

Title: Sources of hepatic glucose production by 2H2O ingestion and Bayesian analysis of 2H glucuronide enrichment.

Journal: Magnetic resonance in medicine 20080901

Title: Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

Journal: Journal of medicinal chemistry 20080612

Title: Development of an HPLC-MS/MS method for the selective determination of paracetamol metabolites in mouse urine.

Journal: Analytical biochemistry 20080301

Title: Hepatic synthesis and urinary elimination of acetaminophen glucuronide are exacerbated in bile duct-ligated rats.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080301

Title: Evidence that processes other than gluconeogenesis may influence the ratio of deuterium on the fifth and third carbons of glucose: implications for the use of 2H2O to measure gluconeogenesis in humans.

Journal: Diabetes 20080101

Title: Beneficial effect of spironolactone administration on ethynylestradiol-induced cholestasis in the rat: involvement of up-regulation of multidrug resistance-associated protein 2.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20071101

Title: Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.

Journal: International journal of clinical pharmacology and therapeutics 20070901

Title: Expression of 25 human ABC transporters in the yeast Pichia pastoris and characterization of the purified ABCC3 ATPase activity.

Journal: Biochemistry 20070710

Title: Evidence for function of UDP galactose pyrophosphorylase in mice with absent galactose-1-phosphate uridyltransferase.

Journal: Molecular genetics and metabolism 20070601

Title: Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life.

Journal: Methods and findings in experimental and clinical pharmacology 20070501

Title: Effects of combined UDP-glucuronosyltransferase (UGT) 1A1*28 and 1A6*2 on paracetamol pharmacokinetics in beta-thalassemia/HbE.

Journal: Pharmacology 20070101

Title: Glucuronidation in the chimpanzee (Pan troglodytes): studies with acetaminophen, oestradiol and morphine.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20061201

Title: A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients.

Journal: European journal of clinical pharmacology 20060901

Title: Noninvasive analysis of hepatic glycogen kinetics before and after breakfast with deuterated water and acetaminophen.

Journal: Diabetes 20060801

Title: Identification of phenacetin metabolites in human urine after administration of phenacetin-C2H3: measurement of futile metabolic deacetylation via HPLC/MS-SPE-NMR and HPLC-ToF MS.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20060701

Title: Ethynylestradiol increases expression and activity of rat liver MRP3.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060601

Title: Pathways of galactose metabolism by galactosemics: evidence for galactose conversion to hepatic UDPglucose.

Journal: Molecular genetics and metabolism 20060201

Title: Comments on 'shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats'.

Journal: The Journal of pharmacology and experimental therapeutics 20060201

Title: Global systems biology, personalized medicine and molecular epidemiology.

Journal: Molecular systems biology 20060101

Title: Altered disposition of acetaminophen in mice with a disruption of the Mrp3 gene.

Journal: Hepatology (Baltimore, Md.) 20051101

Title: Intra- and interindividual variability of glucuronidation of paracetamol during repeated administration of propacetamol in neonates.

Journal: Acta paediatrica (Oslo, Norway : 1992) 20050901

Title: Effect of taurine on biliary excretion and metabolism of acetaminophen in male hamsters.

Journal: Biological & pharmaceutical bulletin 20041101

Title: Glucose production pathways by 2H and 13C NMR in patients with HIV-associated lipoatrophy.

Journal: Magnetic resonance in medicine 20040401

Title: The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay.

Journal: Journal of pharmaceutical and biomedical analysis 20040218

Title: Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030901

Title: Higher insulin concentrations are required to suppress gluconeogenesis than glycogenolysis in nondiabetic humans.

Journal: Diabetes 20030901

Title: Paracetamol and metabolite pharmacokinetics in infants.

Journal: European journal of clinical pharmacology 20030701

Title: Hepatobiliary excretion of acetaminophen glutathione conjugate and its derivatives in transport-deficient (TR-) hyperbilirubinemic rats.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030601

Title: Transiently altered acetaminophen metabolism after liver transplantation.

Journal: Clinical pharmacology and therapeutics 20030601

Title: Analysis of acetaminophen glucuronide conjugate accompanied by adduct ion production by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20030115

Title: Noninvasive evaluation of liver metabolism by 2H and 13C NMR isotopomer analysis of human urine.

Journal: Analytical biochemistry 20030115

Title: Feasibility of atmospheric pressure desorption/ionization on silicon mass spectrometry in analysis of drugs.

Journal: Rapid communications in mass spectrometry : RCM 20030101

Title: Mechanisms of impaired biliary excretion of acetaminophen glucuronide after acute phenobarbital treatment or phenobarbital pretreatment.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020901

Title: Effect of enteral vs. parenteral glucose delivery on initial splanchnic glucose uptake in nondiabetic humans.

Journal: American journal of physiology. Endocrinology and metabolism 20020801

Title: Effect of nizatidine on paracetamol and its metabolites in human plasma.

Journal: The Journal of pharmacy and pharmacology 20020601

Title: Acetaminophen and metabolite: lack of effect on nitric oxide synthase (constitutive or inducible).

Journal: Headache 20020301

Title: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms.

Journal: The Journal of pharmacology and experimental therapeutics 20011201

Title: An integrated (2)H and (13)C NMR study of gluconeogenesis and TCA cycle flux in humans.

Journal: American journal of physiology. Endocrinology and metabolism 20011001

Title: Methods for measuring glycogen cycling.

Journal: American journal of physiology. Endocrinology and metabolism 20010901

Title: Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man.

Journal: The Journal of pharmacy and pharmacology 20010701

Title: Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen.

Journal: Blood 20010615

Title: Type I diabetes mellitus does not alter initial splanchnic glucose extraction or hepatic UDP-glucose flux during enteral glucose administration.

Journal: Diabetologia 20010601

Title: High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010405

Title: Tissue distribution and interindividual variation in human UDP-glucuronosyltransferase activity: relationship between UGT1A1 promoter genotype and variability in a liver bank.

Journal: Pharmacogenetics 20001101

Title: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.

Journal: The Journal of biological chemistry 20000211

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Tags:16110-10-4 Molecular Formula|16110-10-4 MDL|16110-10-4 SMILES|16110-10-4 acetaminophen glucuronide