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
Zebrafish teratogenicity test with metabolic activation (mDarT): effects of phase I activation of acetaminophen on zebrafish Danio rerio embryos.	2010-09-10	20566340
Differential effect of covalent protein modification and glutathione depletion on the transcriptional response of Nrf2 and NF-kappaB.	2010-08-01	20416283
c-Jun N-terminal kinase modulates oxidant stress and peroxynitrite formation independent of inducible nitric oxide synthase in acetaminophen hepatotoxicity.	2010-07	20423716
Enzyme immobilized magnetic nanoparticles for in-line capillary electrophoresis and drug biotransformation studies: application to paracetamol.	2010-07	20402645
Use of pharmaco-metabonomics for early prediction of acetaminophen-induced hepatotoxicity in humans.	2010-07	20182423
Genetic analysis of cytoprotective functions supported by graded expression of Keap1.	2010-06	20404090
Susceptibility to acetaminophen (APAP) toxicity unexpectedly is decreased during acute viral hepatitis in mice.	2010-05-01	20036646
The effect of acetaminophen nanoparticles on liver toxicity in a rat model.	2010-04-07	20463935
Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1.	2010-03	20166895
Electrochemical evidences in oxidation of acetaminophen in the presence of glutathione and N-acetylcysteine.	2010-01-21	20066308
Mechanism of protection by metallothionein against acetaminophen hepatotoxicity.	2010-01-15	19835899
Zinc Supplementation with Polaprezinc Protects Mouse Hepatocytes against Acetaminophen-Induced Toxicity via Induction of Heat Shock Protein 70.	2010-01	20104264
Fluorescence-based liver microsomal assay for screening of pharmaceutical reactive metabolites using a glutathione conjugated 96-well plate.	2010-01	19957910
Acetaminophen dosing of humans results in blood transcriptome and metabolome changes consistent with impaired oxidative phosphorylation.	2010-01	19918972
The role of para-aminophenol in acetaminophen-induced methemoglobinemia in dogs and cats.	2009-12	20444014
[Dosing time based on molecular mechanism of biological clock of hepatic drug metabolic enzyme].	2009-11	19881208
Life-threatening hyponatremia due to intravenous n-acetylcysteine treatment in an infant: a case report.	2009-09-01	19918421
Beta-catenin activation promotes liver regeneration after acetaminophen-induced injury.	2009-09	19679878
Reduced exposure of imatinib after coadministration with acetaminophen in mice.	2009-08	20523867
Pharmacokinetics of acetaminophen-protein adducts in adults with acetaminophen overdose and acute liver failure.	2009-08	19439490
Management of the critically poisoned patient.	2009-06-29	19563673
The protective effects of garlic extract against acetaminophen-induced oxidative stress and glutathione depletion.	2009-05-15	19806806
Altered disposition of acetaminophen in Nrf2-null and Keap1-knockdown mice.	2009-05	19246624
Metabolism of acetaminophen (paracetamol) in plants--two independent pathways result in the formation of a glutathione and a glucose conjugate.	2009-03	19145453
Structural and kinetic analyses of macrophage migration inhibitory factor active site interactions.	2009-01-13	19090677
Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes.	2009-01	19219744
Reduced acetaminophen-induced liver injury in mice by genetic disruption of IL-1 receptor antagonist.	2009-01	19002106
Current concepts of mechanisms in drug-induced hepatotoxicity.	2009	19689281
Prolonged treatment with N-acetylcystine delays liver recovery from acetaminophen hepatotoxicity.	2009	19358737
The hepatotoxic metabolite of acetaminophen directly activates the Keap1-Nrf2 cell defense system.	2008-10	18785192
Prevention of acetaminophen (APAP)-induced hepatotoxicity by leflunomide via inhibition of APAP biotransformation to N-acetyl-p-benzoquinone imine.	2008-08-28	18588957
Interspecies differences in acetaminophen sensitivity of human, rat, and mouse primary hepatocytes.	2008-06	18346862
Mitochondrial protein thiol modifications in acetaminophen hepatotoxicity: effect on HMG-CoA synthase.	2008-04-01	18313239
Acetaminophen-induced liver damage in mice: effects of some medicinal plants on the oxidative defense system.	2008-03	18054472
Glutathione-S-transferase pi as a model protein for the characterisation of chemically reactive metabolites.	2008-01	18203258
Automated detection of covalent adducts to human serum albumin by immunoaffinity chromatography, on-line solution phase digestion and liquid chromatography-mass spectrometry.	2007-11-15	17913598
Are we getting enough sulfur in our diet?	2007-11-06	17986345
Glutamate cysteine ligase modifier subunit deficiency and gender as determinants of acetaminophen-induced hepatotoxicity in mice.	2007-10	17584759
Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.	2007-09	17907592
Analgesic and anti-inflammatory drug use and risk of bladder cancer: a population based case control study.	2007-08-10	17692123
Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin.	2007-08	17510247
Role of CYP3A and CYP2E1 in alcohol-mediated increases in acetaminophen hepatotoxicity: comparison of wild-type and Cyp2e1(-/-) mice.	2007-07	17392391
Protein targets of reactive electrophiles in human liver microsomes.	2007-06	17480101
The effect of acetaminophen (four grams a day for three consecutive days) on hepatic tests in alcoholic patients--a multicenter randomized study.	2007-05-30	17537264
Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism.	2007-05	17447796
Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen.	2007-02-12	17188792
Pharmacokinetics/pharmacodynamics of acetaminophen analgesia in Japanese patients with chronic pain.	2007-01	17202677
Abstracts of papers presented at the 2007 pittsburgh conference.	2007	18528514
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
Chronoamperometric determination of paracetamol using an avocado tissue (Persea americana) biosensor.	2001-10-31	18968415

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:36:56 GMT 2025` Edited by `admin` on `Mon Mar 31 19:36:56 GMT 2025`
Record UNII	G6S9BN13TI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETIMIDOQUINONE [MI]

Preferred Name

English

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

Code System Code Type Description

MERCK INDEX

m1326