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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17NO8
Molecular Weight 327.2872
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETAMINOPHEN GLUCURONIDE

SMILES

CC(=Nc1ccc(cc1)O[C@@]2([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C(=O)O)O2)O)O)O)O

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 327.2872
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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
High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes.
2001 Apr 5
Cisapride raises the bioavailability of paracetamol by inhibiting its glucuronidation in man.
2001 Jul
Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen.
2001 Jun 15
Effect of nizatidine on paracetamol and its metabolites in human plasma.
2002 Jun
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
Transiently altered acetaminophen metabolism after liver transplantation.
2003 Jun
Hepatobiliary excretion of acetaminophen glutathione conjugate and its derivatives in transport-deficient (TR-) hyperbilirubinemic rats.
2003 Jun
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
Altered disposition of acetaminophen in mice with a disruption of the Mrp3 gene.
2005 Nov
Intra- and interindividual variability of glucuronidation of paracetamol during repeated administration of propacetamol in neonates.
2005 Sep
Global systems biology, personalized medicine and molecular epidemiology.
2006
Comments on "shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats".
2006 Feb
Pathways of galactose metabolism by galactosemics: evidence for galactose conversion to hepatic UDPglucose.
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
Expression of 25 human ABC transporters in the yeast Pichia pastoris and characterization of the purified ABCC3 ATPase activity.
2007 Jul 10
Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life.
2007 May
Effect of the acute phase response induced by endotoxin administration on the expression and activity of UGT isoforms in rats.
2008 Dec
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
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
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.
2009 May
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:59:50 UTC 2021
Edited
by admin
on Sat Jun 26 10:59:50 UTC 2021
Record UNII
8BE7G9R76X
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 10:59:50 UTC 2021 , Edited by admin on Sat Jun 26 10:59:50 UTC 2021
PRIMARY
MESH
C037386
Created by admin on Sat Jun 26 10:59:50 UTC 2021 , Edited by admin on Sat Jun 26 10:59:50 UTC 2021
PRIMARY
FDA UNII
8BE7G9R76X
Created by admin on Sat Jun 26 10:59:50 UTC 2021 , Edited by admin on Sat Jun 26 10:59:50 UTC 2021
PRIMARY
CAS
16110-10-4
Created by admin on Sat Jun 26 10:59:50 UTC 2021 , Edited by admin on Sat Jun 26 10:59:50 UTC 2021
PRIMARY
Related Record Type Details
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