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Details

Stereochemistry ACHIRAL
Molecular Formula C8H7NO2
Molecular Weight 149.1467
Optical Activity UNSPECIFIED
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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Protective effect of stiripentol on acetaminophen-induced hepatotoxicity in rat.
2001 Feb 1
Acetaminophen poisoning: an update for the intensivist.
2002 Apr
Cloning, expression and characterisation of a human Nudix hydrolase specific for adenosine 5'-diphosphoribose (ADP-ribose).
2002 Jan 31
Reduction of toxic metabolite formation of acetaminophen.
2002 Mar 8
Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR.
2002 Oct 11
Toxicology. Protecting liver from painkiller's lethal dose.
2002 Oct 11
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
NF-kappaB, macrophage migration inhibitory factor and cyclooxygenase-inhibitions as likely mechanisms behind the acetaminophen- and NSAID-prevention of the ovarian cancer.
2004
Cytoprotection following endoplasmic reticulum stress protein induction in continuous cell lines.
2004 Mar
N-acetyl-p-benzoquinone imine, the toxic metabolite of acetaminophen, is a topoisomerase II poison.
2004 Mar 30
Intravenous paracetamol (propacetamol) pharmacokinetics in term and preterm neonates.
2004 May
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
Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone imine.
2006 Jan 15
Abstracts of papers presented at the 2007 pittsburgh conference.
2007
Use of a standardised and validated long-term human hepatocyte culture system for repetitive analyses of drugs: repeated administrations of acetaminophen reduces albumin and urea secretion.
2007
Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen.
2007 Feb 12
Role of CYP3A and CYP2E1 in alcohol-mediated increases in acetaminophen hepatotoxicity: comparison of wild-type and Cyp2e1(-/-) mice.
2007 Jul
Protein targets of reactive electrophiles in human liver microsomes.
2007 Jun
Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism.
2007 May
Are we getting enough sulfur in our diet?
2007 Nov 6
Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.
2007 Sep
Acetaminophen-induced liver damage in mice: effects of some medicinal plants on the oxidative defense system.
2008 Mar
The hepatotoxic metabolite of acetaminophen directly activates the Keap1-Nrf2 cell defense system.
2008 Oct
Reduced exposure of imatinib after coadministration with acetaminophen in mice.
2009 Aug
The role of para-aminophenol in acetaminophen-induced methemoglobinemia in dogs and cats.
2009 Dec
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.
2009 May
Life-threatening hyponatremia due to intravenous n-acetylcysteine treatment in an infant: a case report.
2009 Sep 1
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
Zinc Supplementation with Polaprezinc Protects Mouse Hepatocytes against Acetaminophen-Induced Toxicity via Induction of Heat Shock Protein 70.
2010 Jan
Fluorescence-based liver microsomal assay for screening of pharmaceutical reactive metabolites using a glutathione conjugated 96-well plate.
2010 Jan
Acetaminophen dosing of humans results in blood transcriptome and metabolome changes consistent with impaired oxidative phosphorylation.
2010 Jan
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
c-Jun N-terminal kinase modulates oxidant stress and peroxynitrite formation independent of inducible nitric oxide synthase in acetaminophen hepatotoxicity.
2010 Jul
Enzyme immobilized magnetic nanoparticles for in-line capillary electrophoresis and drug biotransformation studies: application to paracetamol.
2010 Jul
Use of pharmaco-metabonomics for early prediction of acetaminophen-induced hepatotoxicity in humans.
2010 Jul
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
Susceptibility to acetaminophen (APAP) toxicity unexpectedly is decreased during acute viral hepatitis in mice.
2010 May 1
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 Tue Oct 22 14:09:26 UTC 2019
Edited
by admin
on Tue Oct 22 14:09:26 UTC 2019
Record UNII
G6S9BN13TI
Record Status Validated (UNII)
Record Version
  • Download
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 Tue Oct 22 14:09:26 UTC 2019 , Edited by admin on Tue Oct 22 14:09:26 UTC 2019
PRIMARY Merck Index
PUBCHEM
39763
Created by admin on Tue Oct 22 14:09:26 UTC 2019 , Edited by admin on Tue Oct 22 14:09:26 UTC 2019
PRIMARY
MESH
C028473
Created by admin on Tue Oct 22 14:09:26 UTC 2019 , Edited by admin on Tue Oct 22 14:09:26 UTC 2019
PRIMARY
WIKIPEDIA
NAPQI
Created by admin on Tue Oct 22 14:09:26 UTC 2019 , Edited by admin on Tue Oct 22 14:09:26 UTC 2019
PRIMARY
EPA CompTox
50700-49-7
Created by admin on Tue Oct 22 14:09:26 UTC 2019 , Edited by admin on Tue Oct 22 14:09:26 UTC 2019
PRIMARY
CAS
50700-49-7
Created by admin on Tue Oct 22 14:09:26 UTC 2019 , Edited by admin on Tue Oct 22 14:09:26 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> METABOLITE TOXIC
PARENT -> METABOLITE TOXIC
Metabolite produces hepatic necrosis in man.