Home Aminos acetaminophen glucuronide

acetaminophen glucuronide

CAS No.:
16110-10-4
Catalog Number:
AG00AKLV
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00AKLV
Chemical Name:
acetaminophen glucuronide
CAS Number:
16110-10-4
MDL Number:
MFCD03094680
IUPAC Name:
(2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI:
InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)/t9-,10-,11+,12-,14+/m0/s1
InChI Key:
IPROLSVTVHAQLE-BYNIDDHOSA-N
UNII:
8BE7G9R76X
Properties
Complexity:
437  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
327.095g/mol
Formal Charge:
0
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
327.289g/mol
Monoisotopic Mass:
327.095g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
146A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.8  
Literature
Title Journal
Modulation of O-GlcNAc Levels in the Liver Impacts Acetaminophen-Induced Liver Injury by Affecting Protein Adduct Formation and Glutathione Synthesis. Toxicological sciences : an official journal of the Society of Toxicology 20180401
A cellular model to study drug-induced liver injury in nonalcoholic fatty liver disease: Application to acetaminophen. Toxicology and applied pharmacology 20160201
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. Bioanalysis 20120601
Investigating paracetamol pharmacokinetics using venous and capillary blood and saliva sampling. The Journal of pharmacy and pharmacology 20120501
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 of chromatography. B, Analytical technologies in the biomedical and life sciences 20120415
UDP-glucuronosyltransferase expression in mouse liver is increased in obesity- and fasting-induced steatosis. Drug metabolism and disposition: the biological fate of chemicals 20120201
Imitation of drug metabolism in human liver and cytotoxicity assay using a microfluidic device coupled to mass spectrometric detection. Lab on a chip 20120107
Pharmacokinetics and ocular disposition of paracetamol and paracetamol glucuronide in rabbits with diabetes mellitus induced by alloxan. Pharmacological reports : PR 20120101
The impact of Caesarean delivery on paracetamol and ketorolac pharmacokinetics: a paired analysis. Journal of biomedicine & biotechnology 20120101
Postprandial and fasting hepatic glucose fluxes in long-standing type 1 diabetes. Diabetes 20110601
Effects of imatinib mesylate on the pharmacokinetics of paracetamol (acetaminophen) in Korean patients with chronic myelogenous leukaemia. British journal of clinical pharmacology 20110201
Acetaminophen pharmacokinetics in children with nonalcoholic fatty liver disease. Journal of pediatric gastroenterology and nutrition 20110201
Pharmacokinetics of intravenous paracetamol in elderly patients. Clinical pharmacokinetics 20110201
Comparison of the pharmacokinetics of paracetamol from two generic products in patients after total gastric resection. Pharmacological reports : PR 20110101
Evaluating human liver reserve function by measuring serum concentrations of phenacetin and its metabolites. Journal of digestive diseases 20101201
Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol. International journal of pharmaceutics 20100104
The effect of transcatheter arterial chemoembolization on phase II drug metabolism enzymes in patients with hepatocellular carcinoma. Cancer chemotherapy and pharmacology 20100101
Does rapid metabolism ensure negligible risk from bisphenol A? Environmental health perspectives 20091101
In vivo glucuronidation activity of drugs in neonates: extensive interindividual variability despite their young age. Therapeutic drug monitoring 20090801
Studies of acetaminophen and metabolites in urine and their correlations with toxicity using metabolomics. Drug metabolism letters 20090801
Additional evidence that transaldolase exchange, isotope discrimination during the triose-isomerase reaction, or both occur in humans: effects of type 2 diabetes. Diabetes 20090701
Simultaneous RP-HPLC determination of sotalol, metoprolol, alpha-hydroxymetoprolol, paracetamol and its glucuronide and sulfate metabolites in human urine. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20090601
Effect of repeated administration with subtoxic doses of acetaminophen to rats on enterohepatic recirculation of a subsequent toxic dose. Biochemical pharmacology 20090515
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice. Toxicological sciences : an official journal of the Society of Toxicology 20090501
Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation. Clinical and experimental pharmacology & physiology 20090101
Effect of the acute phase response induced by endotoxin administration on the expression and activity of UGT isoforms in rats. Drug metabolism letters 20081201
Prandial insulin and the systemic appearance of meal-derived glucose in people with type 1 diabetes. Diabetes care 20081101
Sources of hepatic glucose production by 2H2O ingestion and Bayesian analysis of 2H glucuronide enrichment. Magnetic resonance in medicine 20080901
Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Journal of medicinal chemistry 20080612
Development of an HPLC-MS/MS method for the selective determination of paracetamol metabolites in mouse urine. Analytical biochemistry 20080301
Hepatic synthesis and urinary elimination of acetaminophen glucuronide are exacerbated in bile duct-ligated rats. Drug metabolism and disposition: the biological fate of chemicals 20080301
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. Diabetes 20080101
Beneficial effect of spironolactone administration on ethynylestradiol-induced cholestasis in the rat: involvement of up-regulation of multidrug resistance-associated protein 2. Drug metabolism and disposition: the biological fate of chemicals 20071101
Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases. International journal of clinical pharmacology and therapeutics 20070901
Expression of 25 human ABC transporters in the yeast Pichia pastoris and characterization of the purified ABCC3 ATPase activity. Biochemistry 20070710
Evidence for function of UDP galactose pyrophosphorylase in mice with absent galactose-1-phosphate uridyltransferase. Molecular genetics and metabolism 20070601
Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life. Methods and findings in experimental and clinical pharmacology 20070501
Effects of combined UDP-glucuronosyltransferase (UGT) 1A1*28 and 1A6*2 on paracetamol pharmacokinetics in beta-thalassemia/HbE. Pharmacology 20070101
Glucuronidation in the chimpanzee (Pan troglodytes): studies with acetaminophen, oestradiol and morphine. Xenobiotica; the fate of foreign compounds in biological systems 20061201
A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. European journal of clinical pharmacology 20060901
Noninvasive analysis of hepatic glycogen kinetics before and after breakfast with deuterated water and acetaminophen. Diabetes 20060801
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. Xenobiotica; the fate of foreign compounds in biological systems 20060701
Ethynylestradiol increases expression and activity of rat liver MRP3. Drug metabolism and disposition: the biological fate of chemicals 20060601
Pathways of galactose metabolism by galactosemics: evidence for galactose conversion to hepatic UDPglucose. Molecular genetics and metabolism 20060201
Comments on 'shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats'. The Journal of pharmacology and experimental therapeutics 20060201
Global systems biology, personalized medicine and molecular epidemiology. Molecular systems biology 20060101
Altered disposition of acetaminophen in mice with a disruption of the Mrp3 gene. Hepatology (Baltimore, Md.) 20051101
Intra- and interindividual variability of glucuronidation of paracetamol during repeated administration of propacetamol in neonates. Acta paediatrica (Oslo, Norway : 1992) 20050901
Effect of taurine on biliary excretion and metabolism of acetaminophen in male hamsters. Biological & pharmaceutical bulletin 20041101
Glucose production pathways by 2H and 13C NMR in patients with HIV-associated lipoatrophy. Magnetic resonance in medicine 20040401
The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay. Journal of pharmaceutical and biomedical analysis 20040218
Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites. Drug metabolism and disposition: the biological fate of chemicals 20030901
Higher insulin concentrations are required to suppress gluconeogenesis than glycogenolysis in nondiabetic humans. Diabetes 20030901
Paracetamol and metabolite pharmacokinetics in infants. European journal of clinical pharmacology 20030701
Hepatobiliary excretion of acetaminophen glutathione conjugate and its derivatives in transport-deficient (TR-) hyperbilirubinemic rats. Drug metabolism and disposition: the biological fate of chemicals 20030601
Transiently altered acetaminophen metabolism after liver transplantation. Clinical pharmacology and therapeutics 20030601
Analysis of acetaminophen glucuronide conjugate accompanied by adduct ion production by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. Journal of pharmaceutical and biomedical analysis 20030115
Noninvasive evaluation of liver metabolism by 2H and 13C NMR isotopomer analysis of human urine. Analytical biochemistry 20030115
Feasibility of atmospheric pressure desorption/ionization on silicon mass spectrometry in analysis of drugs. Rapid communications in mass spectrometry : RCM 20030101
Mechanisms of impaired biliary excretion of acetaminophen glucuronide after acute phenobarbital treatment or phenobarbital pretreatment. Drug metabolism and disposition: the biological fate of chemicals 20020901
Effect of enteral vs. parenteral glucose delivery on initial splanchnic glucose uptake in nondiabetic humans. American journal of physiology. Endocrinology and metabolism 20020801
Effect of nizatidine on paracetamol and its metabolites in human plasma. The Journal of pharmacy and pharmacology 20020601
Acetaminophen and metabolite: lack of effect on nitric oxide synthase (constitutive or inducible). Headache 20020301
Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. The Journal of pharmacology and experimental therapeutics 20011201
An integrated (2)H and (13)C NMR study of gluconeogenesis and TCA cycle flux in humans. American journal of physiology. Endocrinology and metabolism 20011001
Methods for measuring glycogen cycling. American journal of physiology. Endocrinology and metabolism 20010901
Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man. The Journal of pharmacy and pharmacology 20010701
Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen. Blood 20010615
Type I diabetes mellitus does not alter initial splanchnic glucose extraction or hepatic UDP-glucose flux during enteral glucose administration. Diabetologia 20010601
High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. Journal of chromatography. B, Biomedical sciences and applications 20010405
Tissue distribution and interindividual variation in human UDP-glucuronosyltransferase activity: relationship between UGT1A1 promoter genotype and variability in a liver bank. Pharmacogenetics 20001101
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. The Journal of biological chemistry 20000211
Properties