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
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
| Molecular Formula | C14H17NO8 |
| Molecular Weight | 327.2867 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluating human liver reserve function by measuring serum concentrations of phenacetin and its metabolites. | 2010-12 |
|
| Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol. | 2010-01-04 |
|
| The effect of transcatheter arterial chemoembolization on phase II drug metabolism enzymes in patients with hepatocellular carcinoma. | 2010-01 |
|
| Does rapid metabolism ensure negligible risk from bisphenol A? | 2009-11 |
|
| Studies of acetaminophen and metabolites in urine and their correlations with toxicity using metabolomics. | 2009-08 |
|
| In vivo glucuronidation activity of drugs in neonates: extensive interindividual variability despite their young age. | 2009-08 |
|
| Additional evidence that transaldolase exchange, isotope discrimination during the triose-isomerase reaction, or both occur in humans: effects of type 2 diabetes. | 2009-07 |
|
| Simultaneous RP-HPLC determination of sotalol, metoprolol, alpha-hydroxymetoprolol, paracetamol and its glucuronide and sulfate metabolites in human urine. | 2009-06 |
|
| Effect of repeated administration with subtoxic doses of acetaminophen to rats on enterohepatic recirculation of a subsequent toxic dose. | 2009-05-15 |
|
| Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice. | 2009-05 |
|
| Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation. | 2009-01 |
|
| Effect of the acute phase response induced by endotoxin administration on the expression and activity of UGT isoforms in rats. | 2008-12 |
|
| Prandial insulin and the systemic appearance of meal-derived glucose in people with type 1 diabetes. | 2008-11 |
|
| Sources of hepatic glucose production by 2H2O ingestion and Bayesian analysis of 2H glucuronide enrichment. | 2008-09 |
|
| Development of an HPLC-MS/MS method for the selective determination of paracetamol metabolites in mouse urine. | 2008-03-01 |
|
| Hepatic synthesis and urinary elimination of acetaminophen glucuronide are exacerbated in bile duct-ligated rats. | 2008-03 |
|
| 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. | 2008-01 |
|
| Beneficial effect of spironolactone administration on ethynylestradiol-induced cholestasis in the rat: involvement of up-regulation of multidrug resistance-associated protein 2. | 2007-11 |
|
| Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases. | 2007-09 |
|
| Expression of 25 human ABC transporters in the yeast Pichia pastoris and characterization of the purified ABCC3 ATPase activity. | 2007-07-10 |
|
| Evidence for function of UDP galactose pyrophosphorylase in mice with absent galactose-1-phosphate uridyltransferase. | 2007-06 |
|
| Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life. | 2007-05 |
|
| Effects of combined UDP-glucuronosyltransferase (UGT) 1A1*28 and 1A6*2 on paracetamol pharmacokinetics in beta-thalassemia/HbE. | 2007 |
|
| Glucuronidation in the chimpanzee (Pan troglodytes): studies with acetaminophen, oestradiol and morphine. | 2006-12 |
|
| A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. | 2006-09 |
|
| Noninvasive analysis of hepatic glycogen kinetics before and after breakfast with deuterated water and acetaminophen. | 2006-08 |
|
| 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. | 2006-07 |
|
| Ethynylestradiol increases expression and activity of rat liver MRP3. | 2006-06 |
|
| Comments on "shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats". | 2006-02 |
|
| Pathways of galactose metabolism by galactosemics: evidence for galactose conversion to hepatic UDPglucose. | 2006-02 |
|
| Global systems biology, personalized medicine and molecular epidemiology. | 2006 |
|
| Altered disposition of acetaminophen in mice with a disruption of the Mrp3 gene. | 2005-11 |
|
| Intra- and interindividual variability of glucuronidation of paracetamol during repeated administration of propacetamol in neonates. | 2005-09 |
|
| Effect of taurine on biliary excretion and metabolism of acetaminophen in male hamsters. | 2004-11 |
|
| Glucose production pathways by 2H and 13C NMR in patients with HIV-associated lipoatrophy. | 2004-04 |
|
| The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay. | 2004-02-18 |
|
| Higher insulin concentrations are required to suppress gluconeogenesis than glycogenolysis in nondiabetic humans. | 2003-09 |
|
| Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites. | 2003-09 |
|
| Paracetamol and metabolite pharmacokinetics in infants. | 2003-07 |
|
| Transiently altered acetaminophen metabolism after liver transplantation. | 2003-06 |
|
| Hepatobiliary excretion of acetaminophen glutathione conjugate and its derivatives in transport-deficient (TR-) hyperbilirubinemic rats. | 2003-06 |
|
| Noninvasive evaluation of liver metabolism by 2H and 13C NMR isotopomer analysis of human urine. | 2003-01-15 |
|
| Analysis of acetaminophen glucuronide conjugate accompanied by adduct ion production by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. | 2003-01-15 |
|
| Feasibility of atmospheric pressure desorption/ionization on silicon mass spectrometry in analysis of drugs. | 2003 |
|
| Mechanisms of impaired biliary excretion of acetaminophen glucuronide after acute phenobarbital treatment or phenobarbital pretreatment. | 2002-09 |
|
| Effect of enteral vs. parenteral glucose delivery on initial splanchnic glucose uptake in nondiabetic humans. | 2002-08 |
|
| Effect of nizatidine on paracetamol and its metabolites in human plasma. | 2002-06 |
|
| Acetaminophen and metabolite: lack of effect on nitric oxide synthase (constitutive or inducible). | 2002-03 |
|
| Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. | 2001-12 |
|
| Intracellular inhibition of UDP-glucose dehydrogenase during ethanol oxidation. | 1983-03 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:22:47 GMT 2025
by
admin
on
Mon Mar 31 21:22:47 GMT 2025
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| Record UNII |
8BE7G9R76X
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| Record Status |
Validated (UNII)
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| Record Version |
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C037386
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32636
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8BE7G9R76X
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DTXSID30936449
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16110-10-4
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE INACTIVE |
MAJOR
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