Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H7NO2 |
Molecular Weight | 149.1467 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)N=C1C=CC(=O)C=C1
InChI
InChIKey=URNSECGXFRDEDC-UHFFFAOYSA-N
InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
Molecular Formula | C8H7NO2 |
Molecular Weight | 149.1467 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Approval Year
PubMed
Title | Date | PubMed |
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Research strategies for design and development of NSAIDs: clue to balance potency and toxicity of acetanilide compounds. | 2001 Aug |
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[Effect of bicyclol on acetaminophen-induced hepatotoxicity: energetic metabolism and mitochondrial injury in acetaminophen-intoxicated mice]. | 2001 Oct |
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Should a lower treatment line be used when treating paracetamol poisoning in patients with chronic alcoholism?: a case for. | 2002 |
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Acetaminophen poisoning: an update for the intensivist. | 2002 Apr |
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Selective mitochondrial glutathione depletion by ethanol enhances acetaminophen toxicity in rat liver. | 2002 Aug |
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Genomics and proteomics analysis of acetaminophen toxicity in mouse liver. | 2002 Jan |
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Cloning, expression and characterisation of a human Nudix hydrolase specific for adenosine 5'-diphosphoribose (ADP-ribose). | 2002 Jan 31 |
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Synergetic signaling for apoptosis in vitro by ethanol and acetaminophen. | 2002 Jun |
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Reduction of toxic metabolite formation of acetaminophen. | 2002 Mar 8 |
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Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR. | 2002 Oct 11 |
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[Paracetamol: therapeutic action, pathogenesis and treatment of acute poisonings complicated by severe liver damage]. | 2003 |
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Acetaminophen-induced hepatotoxicity. | 2003 Dec |
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Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice. | 2003 Feb |
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Transiently altered acetaminophen metabolism after liver transplantation. | 2003 Jun |
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Cellular events preceding acetaminophen cataractogenesis studied by confocal fluorescence microscopy. | 2003 Oct |
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NF-kappaB, macrophage migration inhibitory factor and cyclooxygenase-inhibitions as likely mechanisms behind the acetaminophen- and NSAID-prevention of the ovarian cancer. | 2004 |
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Enhanced acetaminophen toxicity by activation of the pregnane X receptor. | 2004 Dec |
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N-acetyl-p-benzoquinone imine, the toxic metabolite of acetaminophen, is a topoisomerase II poison. | 2004 Mar 30 |
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Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol. | 2004 May 4 |
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An update of N-acetylcysteine treatment for acute acetaminophen toxicity in children. | 2005 Apr |
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Role of the nuclear receptor pregnane X receptor in acetaminophen hepatotoxicity. | 2005 Dec |
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Involvement of mitochondrial permeability transition in acetaminophen-induced liver injury in mice. | 2005 Jan |
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Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity II. Possible involvement of the gamma-glutamyl cycle. | 2005 Jan 15 |
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Drug interactions with paracetamol. | 2005 Jan-Feb |
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Protection against paracetamol-induced hepatic injury by prazosin pre-treatment in CD-1 mice. | 2005 Nov 11 |
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[Drug-induced liver injury]. | 2006 Jun |
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Thermodynamically based profiling of drug metabolism and drug-drug metabolic interactions: a case study of acetaminophen and ethanol toxic interaction. | 2006 Mar 20 |
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Mice deficient in Cu,Zn-superoxide dismutase are resistant to acetaminophen toxicity. | 2006 Nov 1 |
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Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin. | 2007 Aug |
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Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen. | 2007 Feb 12 |
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Pharmacokinetics/pharmacodynamics of acetaminophen analgesia in Japanese patients with chronic pain. | 2007 Jan |
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Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism. | 2007 May |
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The effect of acetaminophen (four grams a day for three consecutive days) on hepatic tests in alcoholic patients--a multicenter randomized study. | 2007 May 30 |
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Automated detection of covalent adducts to human serum albumin by immunoaffinity chromatography, on-line solution phase digestion and liquid chromatography-mass spectrometry. | 2007 Nov 15 |
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Mitochondrial protein thiol modifications in acetaminophen hepatotoxicity: effect on HMG-CoA synthase. | 2008 Apr 1 |
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Current concepts of mechanisms in drug-induced hepatotoxicity. | 2009 |
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Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity. | 2009 |
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Reduced exposure of imatinib after coadministration with acetaminophen in mice. | 2009 Aug |
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Pharmacokinetics of acetaminophen-protein adducts in adults with acetaminophen overdose and acute liver failure. | 2009 Aug |
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Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes. | 2009 Jan |
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Reduced acetaminophen-induced liver injury in mice by genetic disruption of IL-1 receptor antagonist. | 2009 Jan |
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Metabolism of acetaminophen (paracetamol) in plants--two independent pathways result in the formation of a glutathione and a glucose conjugate. | 2009 Mar |
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Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice. | 2009 May |
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The effect of acetaminophen nanoparticles on liver toxicity in a rat model. | 2010 Apr 7 |
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Differential effect of covalent protein modification and glutathione depletion on the transcriptional response of Nrf2 and NF-kappaB. | 2010 Aug 1 |
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Mechanism of protection by metallothionein against acetaminophen hepatotoxicity. | 2010 Jan 15 |
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Electrochemical evidences in oxidation of acetaminophen in the presence of glutathione and N-acetylcysteine. | 2010 Jan 21 |
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Genetic analysis of cytoprotective functions supported by graded expression of Keap1. | 2010 Jun |
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Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1. | 2010 Mar |
|
Zebrafish teratogenicity test with metabolic activation (mDarT): effects of phase I activation of acetaminophen on zebrafish Danio rerio embryos. | 2010 Sep 10 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 02:20:53 UTC 2023
by
admin
on
Thu Jul 06 02:20:53 UTC 2023
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Record UNII |
G6S9BN13TI
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Record Status |
Validated (UNII)
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Record Version |
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M1326
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39763
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C028473
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29132
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NAPQI
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DTXSID20198756
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G6S9BN13TI
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50700-49-7
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PARENT -> METABOLITE TOXIC |
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AMOUNT EXCRETED
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PARENT -> METABOLITE TOXIC |
Metabolite produces hepatic necrosis in man.
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