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
Protective effect of stiripentol on acetaminophen-induced hepatotoxicity in rat.	2001 Feb 1	11162779
[About paracetamol again].	2001 Feb 18	11243017
Acetaminophen poisoning: an update for the intensivist.	2002 Apr	11983032
Effects of ethanol dose and ethanol withdrawal on rat liver mitochondrial glutathione: implication of potentiated acetaminophen toxicity in alcoholics.	2002 Dec	12433812
Reduction of toxic metabolite formation of acetaminophen.	2002 Mar 8	11866476
[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
Mangafodipir prevents liver injury induced by acetaminophen in the mouse.	2003 Nov	14568259
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
Enhancement of acetaminophen cytotoxicity in selenium-binding protein-overexpressed COS-1 cells.	2004 Aug	15499197
Cytoprotection following endoplasmic reticulum stress protein induction in continuous cell lines.	2004 Mar	15049342
Intravenous paracetamol (propacetamol) pharmacokinetics in term and preterm neonates.	2004 May	15071761
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.	2004 May 4	15150627
Influence of feeding schedule on 24-h rhythm of hepatotoxicity induced by acetaminophen in mice.	2004 Nov	15205452
Paracetamol (acetaminophen) warfarin interaction: NAPQI, the toxic metabolite of paracetamol, is an inhibitor of enzymes in the vitamin K cycle.	2004 Oct	15467911
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
Role of innate immunity in acetaminophen-induced hepatotoxicity.	2006 Aug	16859400
An experimental design for the controlled modulation of intracellular GSH levels in cultured hepatocytes.	2006 Aug 15	16863994
Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells.	2006 Jul	16632523
[Drug-induced liver injury].	2006 Jun	16880695
Defensive nature of Sargassum polycystum (Brown alga) against acetaminophen-induced toxic hepatitis in rats: role of drug metabolizing microsomal enzyme system, tumor necrosis factor-alpha and fate of liver cell structural integrity.	2006 Jun 28	16804966
Mice deficient in Cu,Zn-superoxide dismutase are resistant to acetaminophen toxicity.	2006 Nov 1	16831125
Multicommuted flow system employing pinch solenoid valves and micro-pumps. Spectrophotometric determination of paracetamol in pharmaceutical formulations.	2006 Oct 11	16730155
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	17361319
Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin.	2007 Aug	17510247
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
Are we getting enough sulfur in our diet?	2007 Nov 6	17986345
Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.	2007 Sep	17907592
Mitochondrial protein thiol modifications in acetaminophen hepatotoxicity: effect on HMG-CoA synthase.	2008 Apr 1	18313239
Acetaminophen-induced liver damage in mice: effects of some medicinal plants on the oxidative defense system.	2008 Mar	18054472
The hepatotoxic metabolite of acetaminophen directly activates the Keap1-Nrf2 cell defense system.	2008 Oct	18785192
Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity.	2009	19358737
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
Structural and kinetic analyses of macrophage migration inhibitory factor active site interactions.	2009 Jan 13	19090677
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
Zinc Supplementation with Polaprezinc Protects Mouse Hepatocytes against Acetaminophen-Induced Toxicity via Induction of Heat Shock Protein 70.	2010 Jan	20104264
Enzyme immobilized magnetic nanoparticles for in-line capillary electrophoresis and drug biotransformation studies: application to paracetamol.	2010 Jul	20402645
Genetic analysis of cytoprotective functions supported by graded expression of Keap1.	2010 Jun	20404090
Susceptibility to acetaminophen (APAP) toxicity unexpectedly is decreased during acute viral hepatitis in mice.	2010 May 1	20036646
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 `Fri Dec 15 19:13:04 GMT 2023` Edited by `admin` on `Fri Dec 15 19:13:04 GMT 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