ACETIMIDOQUINONE

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 Search

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

Title	Date	PubMed
Research strategies for design and development of NSAIDs: clue to balance potency and toxicity of acetanilide compounds.	2001 Aug	11565854
[Effect of bicyclol on acetaminophen-induced hepatotoxicity: energetic metabolism and mitochondrial injury in acetaminophen-intoxicated mice].	2001 Oct	12579967
Should a lower treatment line be used when treating paracetamol poisoning in patients with chronic alcoholism?: a case for.	2002	12137556
Acetaminophen poisoning: an update for the intensivist.	2002 Apr	11983032
Selective mitochondrial glutathione depletion by ethanol enhances acetaminophen toxicity in rat liver.	2002 Aug	12143040
Genomics and proteomics analysis of acetaminophen toxicity in mouse liver.	2002 Jan	11752693
Cloning, expression and characterisation of a human Nudix hydrolase specific for adenosine 5'-diphosphoribose (ADP-ribose).	2002 Jan 31	11825615
Synergetic signaling for apoptosis in vitro by ethanol and acetaminophen.	2002 Jun	12106828
Reduction of toxic metabolite formation of acetaminophen.	2002 Mar 8	11866476
Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR.	2002 Oct 11	12376703
[Paracetamol: therapeutic action, pathogenesis and treatment of acute poisonings complicated by severe liver damage].	2003	14569887
Acetaminophen-induced hepatotoxicity.	2003 Dec	14625346
Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice.	2003 Feb	12547406
Transiently altered acetaminophen metabolism after liver transplantation.	2003 Jun	12811364
Cellular events preceding acetaminophen cataractogenesis studied by confocal fluorescence microscopy.	2003 Oct	14601627
NF-kappaB, macrophage migration inhibitory factor and cyclooxygenase-inhibitions as likely mechanisms behind the acetaminophen- and NSAID-prevention of the ovarian cancer.	2004	15254653
Enhanced acetaminophen toxicity by activation of the pregnane X receptor.	2004 Dec	15456926
N-acetyl-p-benzoquinone imine, the toxic metabolite of acetaminophen, is a topoisomerase II poison.	2004 Mar 30	15035644
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.	2004 May 4	15150627
An update of N-acetylcysteine treatment for acute acetaminophen toxicity in children.	2005 Apr	15800420
Role of the nuclear receptor pregnane X receptor in acetaminophen hepatotoxicity.	2005 Dec	16141365
Involvement of mitochondrial permeability transition in acetaminophen-induced liver injury in mice.	2005 Jan	15629515
Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity II. Possible involvement of the gamma-glutamyl cycle.	2005 Jan 15	15629191
Drug interactions with paracetamol.	2005 Jan-Feb	15662293
Protection against paracetamol-induced hepatic injury by prazosin pre-treatment in CD-1 mice.	2005 Nov 11	16054166
[Drug-induced liver injury].	2006 Jun	16880695
Thermodynamically based profiling of drug metabolism and drug-drug metabolic interactions: a case study of acetaminophen and ethanol toxic interaction.	2006 Mar 20	16314027
Mice deficient in Cu,Zn-superoxide dismutase are resistant to acetaminophen toxicity.	2006 Nov 1	16831125
Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin.	2007 Aug	17510247
Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen.	2007 Feb 12	17188792
Pharmacokinetics/pharmacodynamics of acetaminophen analgesia in Japanese patients with chronic pain.	2007 Jan	17202677
Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism.	2007 May	17447796
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	17537264
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	17913598
Mitochondrial protein thiol modifications in acetaminophen hepatotoxicity: effect on HMG-CoA synthase.	2008 Apr 1	18313239
Current concepts of mechanisms in drug-induced hepatotoxicity.	2009	19689281
Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity.	2009	19358737
Reduced exposure of imatinib after coadministration with acetaminophen in mice.	2009 Aug	20523867
Pharmacokinetics of acetaminophen-protein adducts in adults with acetaminophen overdose and acute liver failure.	2009 Aug	19439490
Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes.	2009 Jan	19219744
Reduced acetaminophen-induced liver injury in mice by genetic disruption of IL-1 receptor antagonist.	2009 Jan	19002106
Metabolism of acetaminophen (paracetamol) in plants--two independent pathways result in the formation of a glutathione and a glucose conjugate.	2009 Mar	19145453
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.	2009 May	19246624
The effect of acetaminophen nanoparticles on liver toxicity in a rat model.	2010 Apr 7	20463935
Differential effect of covalent protein modification and glutathione depletion on the transcriptional response of Nrf2 and NF-kappaB.	2010 Aug 1	20416283
Mechanism of protection by metallothionein against acetaminophen hepatotoxicity.	2010 Jan 15	19835899
Electrochemical evidences in oxidation of acetaminophen in the presence of glutathione and N-acetylcysteine.	2010 Jan 21	20066308
Genetic analysis of cytoprotective functions supported by graded expression of Keap1.	2010 Jun	20404090
Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1.	2010 Mar	20166895
Zebrafish teratogenicity test with metabolic activation (mDarT): effects of phase I activation of acetaminophen on zebrafish Danio rerio embryos.	2010 Sep 10	20566340

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

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