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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
Structure of ACETIMIDOQUINONE

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Research strategies for design and development of NSAIDs: clue to balance potency and toxicity of acetanilide compounds.
2001 Aug
[Effect of bicyclol on acetaminophen-induced hepatotoxicity: energetic metabolism and mitochondrial injury in acetaminophen-intoxicated mice].
2001 Oct
Should a lower treatment line be used when treating paracetamol poisoning in patients with chronic alcoholism?: a case for.
2002
Acetaminophen poisoning: an update for the intensivist.
2002 Apr
Selective mitochondrial glutathione depletion by ethanol enhances acetaminophen toxicity in rat liver.
2002 Aug
Genomics and proteomics analysis of acetaminophen toxicity in mouse liver.
2002 Jan
Cloning, expression and characterisation of a human Nudix hydrolase specific for adenosine 5'-diphosphoribose (ADP-ribose).
2002 Jan 31
Synergetic signaling for apoptosis in vitro by ethanol and acetaminophen.
2002 Jun
Reduction of toxic metabolite formation of acetaminophen.
2002 Mar 8
Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR.
2002 Oct 11
[Paracetamol: therapeutic action, pathogenesis and treatment of acute poisonings complicated by severe liver damage].
2003
Acetaminophen-induced hepatotoxicity.
2003 Dec
Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice.
2003 Feb
Transiently altered acetaminophen metabolism after liver transplantation.
2003 Jun
Cellular events preceding acetaminophen cataractogenesis studied by confocal fluorescence microscopy.
2003 Oct
NF-kappaB, macrophage migration inhibitory factor and cyclooxygenase-inhibitions as likely mechanisms behind the acetaminophen- and NSAID-prevention of the ovarian cancer.
2004
Enhanced acetaminophen toxicity by activation of the pregnane X receptor.
2004 Dec
N-acetyl-p-benzoquinone imine, the toxic metabolite of acetaminophen, is a topoisomerase II poison.
2004 Mar 30
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.
2004 May 4
An update of N-acetylcysteine treatment for acute acetaminophen toxicity in children.
2005 Apr
Role of the nuclear receptor pregnane X receptor in acetaminophen hepatotoxicity.
2005 Dec
Involvement of mitochondrial permeability transition in acetaminophen-induced liver injury in mice.
2005 Jan
Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity II. Possible involvement of the gamma-glutamyl cycle.
2005 Jan 15
Drug interactions with paracetamol.
2005 Jan-Feb
Protection against paracetamol-induced hepatic injury by prazosin pre-treatment in CD-1 mice.
2005 Nov 11
[Drug-induced liver injury].
2006 Jun
Thermodynamically based profiling of drug metabolism and drug-drug metabolic interactions: a case study of acetaminophen and ethanol toxic interaction.
2006 Mar 20
Mice deficient in Cu,Zn-superoxide dismutase are resistant to acetaminophen toxicity.
2006 Nov 1
Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin.
2007 Aug
Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen.
2007 Feb 12
Pharmacokinetics/pharmacodynamics of acetaminophen analgesia in Japanese patients with chronic pain.
2007 Jan
Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism.
2007 May
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
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
Mitochondrial protein thiol modifications in acetaminophen hepatotoxicity: effect on HMG-CoA synthase.
2008 Apr 1
Current concepts of mechanisms in drug-induced hepatotoxicity.
2009
Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity.
2009
Reduced exposure of imatinib after coadministration with acetaminophen in mice.
2009 Aug
Pharmacokinetics of acetaminophen-protein adducts in adults with acetaminophen overdose and acute liver failure.
2009 Aug
Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes.
2009 Jan
Reduced acetaminophen-induced liver injury in mice by genetic disruption of IL-1 receptor antagonist.
2009 Jan
Metabolism of acetaminophen (paracetamol) in plants--two independent pathways result in the formation of a glutathione and a glucose conjugate.
2009 Mar
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.
2009 May
The effect of acetaminophen nanoparticles on liver toxicity in a rat model.
2010 Apr 7
Differential effect of covalent protein modification and glutathione depletion on the transcriptional response of Nrf2 and NF-kappaB.
2010 Aug 1
Mechanism of protection by metallothionein against acetaminophen hepatotoxicity.
2010 Jan 15
Electrochemical evidences in oxidation of acetaminophen in the presence of glutathione and N-acetylcysteine.
2010 Jan 21
Genetic analysis of cytoprotective functions supported by graded expression of Keap1.
2010 Jun
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 Thu Jul 06 02:20:53 UTC 2023
Edited
by admin
on Thu Jul 06 02:20:53 UTC 2023
Record UNII
G6S9BN13TI
Record Status Validated (UNII)
Record Version
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Name Type Language
ACETIMIDOQUINONE
MI  
Common Name English
N-ACETYL-P-BENZOQUINONIMINE
Common Name English
NAPQI
Common Name English
ACETAMIDE, N-(4-OXO-2,5-CYCLOHEXADIEN-1-YLIDENE)-
Systematic Name English
N-ACETYL-P-BENZOQUINONE IMINE
Common Name English
N-ACETYL-P-QUINONEIMINE
Common Name English
N-ACETYL-4-BENZOQUINONEIMINE
Systematic Name English
ACETIMIDOQUINONE [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
M1326
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY Merck Index
PUBCHEM
39763
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
MESH
C028473
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
CHEBI
29132
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
WIKIPEDIA
NAPQI
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID20198756
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
FDA UNII
G6S9BN13TI
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
CAS
50700-49-7
Created by admin on Thu Jul 06 02:20:53 UTC 2023 , Edited by admin on Thu Jul 06 02:20:53 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE TOXIC
Metabolite produced hepatic necrosis in man.
AMOUNT EXCRETED
URINE
PARENT -> METABOLITE TOXIC
Metabolite produces hepatic necrosis in man.