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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17NO8
Molecular Weight 327.2867
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETAMINOPHEN GLUCURONIDE

SMILES

CC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1

InChI

InChIKey=IPROLSVTVHAQLE-BYNIDDHOSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H17NO8
Molecular Weight 327.2867
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Intracellular inhibition of UDP-glucose dehydrogenase during ethanol oxidation.
1983 Mar
Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms.
2001 Dec
Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man.
2001 Jul
Type I diabetes mellitus does not alter initial splanchnic glucose extraction or hepatic UDP-glucose flux during enteral glucose administration.
2001 Jun
An integrated (2)H and (13)C NMR study of gluconeogenesis and TCA cycle flux in humans.
2001 Oct
Methods for measuring glycogen cycling.
2001 Sep
Effect of enteral vs. parenteral glucose delivery on initial splanchnic glucose uptake in nondiabetic humans.
2002 Aug
Effect of nizatidine on paracetamol and its metabolites in human plasma.
2002 Jun
Acetaminophen and metabolite: lack of effect on nitric oxide synthase (constitutive or inducible).
2002 Mar
Mechanisms of impaired biliary excretion of acetaminophen glucuronide after acute phenobarbital treatment or phenobarbital pretreatment.
2002 Sep
Feasibility of atmospheric pressure desorption/ionization on silicon mass spectrometry in analysis of drugs.
2003
Noninvasive evaluation of liver metabolism by 2H and 13C NMR isotopomer analysis of human urine.
2003 Jan 15
Analysis of acetaminophen glucuronide conjugate accompanied by adduct ion production by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.
2003 Jan 15
Paracetamol and metabolite pharmacokinetics in infants.
2003 Jul
Transiently altered acetaminophen metabolism after liver transplantation.
2003 Jun
Higher insulin concentrations are required to suppress gluconeogenesis than glycogenolysis in nondiabetic humans.
2003 Sep
Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites.
2003 Sep
Glucose production pathways by 2H and 13C NMR in patients with HIV-associated lipoatrophy.
2004 Apr
The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay.
2004 Feb 18
Effect of taurine on biliary excretion and metabolism of acetaminophen in male hamsters.
2004 Nov
Altered disposition of acetaminophen in mice with a disruption of the Mrp3 gene.
2005 Nov
Global systems biology, personalized medicine and molecular epidemiology.
2006
Noninvasive analysis of hepatic glycogen kinetics before and after breakfast with deuterated water and acetaminophen.
2006 Aug
Glucuronidation in the chimpanzee (Pan troglodytes): studies with acetaminophen, oestradiol and morphine.
2006 Dec
Comments on "shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats".
2006 Feb
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.
2006 Jul
Ethynylestradiol increases expression and activity of rat liver MRP3.
2006 Jun
A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients.
2006 Sep
Expression of 25 human ABC transporters in the yeast Pichia pastoris and characterization of the purified ABCC3 ATPase activity.
2007 Jul 10
Evidence for function of UDP galactose pyrophosphorylase in mice with absent galactose-1-phosphate uridyltransferase.
2007 Jun
Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life.
2007 May
Beneficial effect of spironolactone administration on ethynylestradiol-induced cholestasis in the rat: involvement of up-regulation of multidrug resistance-associated protein 2.
2007 Nov
Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.
2007 Sep
Effect of the acute phase response induced by endotoxin administration on the expression and activity of UGT isoforms in rats.
2008 Dec
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.
2008 Jan
Hepatic synthesis and urinary elimination of acetaminophen glucuronide are exacerbated in bile duct-ligated rats.
2008 Mar
Development of an HPLC-MS/MS method for the selective determination of paracetamol metabolites in mouse urine.
2008 Mar 1
Prandial insulin and the systemic appearance of meal-derived glucose in people with type 1 diabetes.
2008 Nov
Sources of hepatic glucose production by 2H2O ingestion and Bayesian analysis of 2H glucuronide enrichment.
2008 Sep
Studies of acetaminophen and metabolites in urine and their correlations with toxicity using metabolomics.
2009 Aug
In vivo glucuronidation activity of drugs in neonates: extensive interindividual variability despite their young age.
2009 Aug
Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation.
2009 Jan
Additional evidence that transaldolase exchange, isotope discrimination during the triose-isomerase reaction, or both occur in humans: effects of type 2 diabetes.
2009 Jul
Simultaneous RP-HPLC determination of sotalol, metoprolol, alpha-hydroxymetoprolol, paracetamol and its glucuronide and sulfate metabolites in human urine.
2009 Jun
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.
2009 May
Effect of repeated administration with subtoxic doses of acetaminophen to rats on enterohepatic recirculation of a subsequent toxic dose.
2009 May 15
Does rapid metabolism ensure negligible risk from bisphenol A?
2009 Nov
Evaluating human liver reserve function by measuring serum concentrations of phenacetin and its metabolites.
2010 Dec
The effect of transcatheter arterial chemoembolization on phase II drug metabolism enzymes in patients with hepatocellular carcinoma.
2010 Jan
Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol.
2010 Jan 4
Substance Class Chemical
Created
by admin
on Tue Oct 22 18:45:01 UTC 2019
Edited
by admin
on Tue Oct 22 18:45:01 UTC 2019
Record UNII
8BE7G9R76X
Record Status Validated (UNII)
Record Version
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Name Type Language
ACETAMINOPHEN GLUCURONIDE
Common Name English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 4-(ACETYLAMINO)PHENYL
Common Name English
4-GLUCURONOSIDOACETANILIDE
Common Name English
PARACETAMOL GLUCURONIDE
Common Name English
Code System Code Type Description
PUBCHEM
83944
Created by admin on Tue Oct 22 18:45:02 UTC 2019 , Edited by admin on Tue Oct 22 18:45:02 UTC 2019
PRIMARY
MESH
C037386
Created by admin on Tue Oct 22 18:45:02 UTC 2019 , Edited by admin on Tue Oct 22 18:45:02 UTC 2019
PRIMARY
CAS
16110-10-4
Created by admin on Tue Oct 22 18:45:02 UTC 2019 , Edited by admin on Tue Oct 22 18:45:02 UTC 2019
PRIMARY
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