Compounds > quinocetone
Page last updated: 2024-08-01 18:24:45

quinocetone

Description

quinocetone: structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID5387181
CHEMBL ID497740
MeSH IDM0488018

Synonyms (16)

Synonym
nsc-621477
nsc621477
CHEMBL497740
(e)-1-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-3-phenylprop-2-en-1-one
quinocetone
81810-66-4
2-cinnamoyl-3-methylquinoxaline 1,4-dioxide
AKOS015889503
85108-59-4
HY-123581
AS-16001
mfcd09753267
CS-0083565
CCG-267535
D70399
2-cinnamoyl-3-methylquinoxaline1,4-dioxide

Bioassays (15)

Assay IDTitleYearJournalArticle
AID515221Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 by microplate alamar blue assay2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
ISSN: 1768-3254		E-2-[3-(3,4-dichlorophenyl)-1-oxo-2-propenyl]-3-methylquinoxaline-1,4-dioxide: a lead antitubercular agent which alters mitochondrial respiration in rat liver.
AID398099Cytotoxicity against human HSC2 cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398103Growth inhibition of human CEM cells at 10 uM after 3 days relative to melphalan2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398093Reversal of P-glycoprotein-mediated multidrug resistance in human MDR1 gene transfected mouse L5178Y cells assessed as fluorescence activity ratio at 200 uM by rhodamine 123 accumulation assay2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID1294351Antimicrobial activity against Mycobacterium tuberculosis H37Rv ATCC 27294 incubated for 7 days by BacTiter-Glo cell viability assay2016Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9
ISSN: 1464-3405		Design and synthesis of novel quinoxaline derivatives as potential candidates for treatment of multidrug-resistant and latent tuberculosis.
AID398090Growth inhibition of human Molt4/C8 cells after 3 days2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398098Cytotoxicity against human HL60 cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398095Cytotoxicity against human HGF cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398100Cytotoxicity against human HSC3 cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398091Growth inhibition of human CEM cells after 3 days2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398092Reversal of P-glycoprotein-mediated multidrug resistance in human MDR1 gene transfected mouse L5178Y cells assessed as fluorescence activity ratio at 20 uM by rhodamine 123 accumulation assay2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398102Growth inhibition of human Molt4/C8 cells at 10 uM after 3 days relative to melphalan2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398097Cytotoxicity against human HPLF cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398101Cytotoxicity against human HSC4 cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.
AID398096Cytotoxicity against human HPC cells after 48 hrs2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
ISSN: 1464-3391		2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: a novel cluster of tumor-specific cytotoxins which reverse multidrug resistance.

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (6.82)29.6817
2010's39 (88.64)24.3611
2020's2 (4.55)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.17%)5.53%
Reviews1 (2.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other44 (95.65%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
verapamil
1
aromatic ether;
nitrile;
polyether;
tertiary amino compound		2009200915.0low000100
isoniazid
1
carbohydrazideantitubercular agent;
drug allergen		201620168.0low000010
pyrimethamine
1
aminopyrimidine;
monochlorobenzenes		antimalarial;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor		201620168.0low000010
cycloserine
1
4-amino-1,2-oxazolidin-3-one;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic;
zwitterion		antiinfective agent;
antimetabolite;
antitubercular agent;
metabolite;
NMDA receptor agonist		201620168.0low000010
ethambutol
1
ethanolamines;
ethylenediamine derivative		antitubercular agent;
environmental contaminant;
xenobiotic		201620168.0low000010
amikacin
1
alpha-D-glucoside;
amino cyclitol glycoside;
aminoglycoside;
carboxamide		antibacterial drug;
antimicrobial agent;
nephrotoxin		201620168.0low000010
mequindox
2
2009201014.5low000200
melphalan
1
L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent		2009200915.0low000100
rifampin
1
cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor		201620168.0low000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
ml 7
1
N-sulfonyldiazepane;
organoiodine compound		EC 2.7.11.18 (myosin-light-chain kinase) inhibitor201620168.0low000010
sulfameter
1
pyrimidines;
sulfonamide antibiotic;
sulfonamide		antiinfective agent;
leprostatic drug;
renal agent		2014201410.0low000010
sulfaquinoxaline
1
benzenes;
sulfonamide		2014201410.0low000010
aldosterone
2
11beta-hydroxy steroid;
18-oxo steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid hormone;
mineralocorticoid;
primary alpha-hydroxy ketone;
steroid aldehyde		human metabolite;
mouse metabolite		201620168.0low000020
quinoxalines
41
mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene		2009202210.0high1005342
malondialdehyde
2
dialdehydebiomarker2013201410.5low000020
enrofloxacin
1
cyclopropanes;
N-alkylpiperazine;
N-arylpiperazine;
organofluorine compound;
quinolinemonocarboxylic acid;
quinolone		antibacterial agent;
antimicrobial agent;
antineoplastic agent		202120213.0low000001
olaquindox
5
quinoxaline derivative2009201312.8low000230
quindoxin
1
quinoxaline derivative201620168.0low000010
procyanidin
1
proanthocyanidin201620168.0low000010
mequindox
6
201120179.8medium000060
curcumin
3
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger		201520168.7low000030
mtt formazan
1
2009200915.0low000100
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid
1
201820186.0low000010
3-methylquinoxaline-2-carboxylic acid
1
2014201410.0low000010
formazans
1
2009200915.0low000100
colistin
1
202120213.0low000001
oxytetracycline, anhydrous
1
202220222.0low000001
deoxyguanosine
1
purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		2014201410.0low000010
cyadox
3
2013201610.0low000030
8-hydroxy-2'-deoxyguanosine
1
guanosinesbiomarker2014201410.0low000010
carbadox
3
quinoxaline derivative2009201312.3low000120
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Acute Liver Injury, Drug-Induced0
1
202220222.0low000001
Adrenal Cortex Cancer0
1
201620168.0low000010
Adrenal Cortex Neoplasms0
1
201620168.0low000010
Adrenal Gland Diseases0
1
201620168.0low000010
Benign Neoplasms0
1
2009200915.0low000100
Body Weight0
3
2010201412.0medium000120
Chemical and Drug Induced Liver Injury0
1
202220222.0low000001
Chromosome-Defective Micronuclei0
3
2009201312.3medium000120
E coli Infections0
1
201520159.0low000010
Enterocolitis0
1
201520159.0low000010
Escherichia coli Infections0
1
201520159.0low000010
Inflammation0
1
201620168.0low000010
Innate Inflammatory Response0
1
201620168.0low000010
Kidney Diseases0
2
2012201311.5low000020
Koch's Disease0
1
2010201014.0low000100
Latent Tuberculosis0
1
201620168.0low000010
Necrosis0
1
201520159.0low000010
Neoplasms0
1
2009200915.0low000100
Sensitivity and Specificity0
1
2010201014.0low000100
Tuberculosis0
1
2010201014.0low000100
Tuberculosis, Drug-Resistant0
1
201620168.0low000010
Tuberculosis, Multidrug-Resistant0
1
201620168.0low000010

Safety/Toxicity (9)

ArticleYear
Combination of oxytetracycline and quinocetone synergistically induces hepatotoxicity via generation of reactive oxygen species and activation of mitochondrial pathway.
Toxicology mechanisms and methods, , Volume: 32, Issue:1		2022
High risk of adrenal toxicity of N1-desoxy quinoxaline 1,4-dioxide derivatives and the protection of oligomeric proanthocyanidins (OPC) in the inhibition of the expression of aldosterone synthetase in H295R cells.
Toxicology, , Feb-03, Volume: 341-343		2016
Roles of ROS mediated oxidative stress and DNA damage in 3-methyl-2-quinoxalin benzenevinylketo-1, 4-dioxide-induced immunotoxicity of Sprague-Dawley rats.
Regulatory toxicology and pharmacology : RTP, , Volume: 73, Issue:2		2015
Mechanism of adrenocortical toxicity induced by quinocetone and its bidesoxy-quinocetone metabolite in porcine adrenocortical cells in vitro.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, , Volume: 84		2015
Curcumin attenuates quinocetone-induced oxidative stress and genotoxicity in human hepatocyte L02 cells.
Toxicology mechanisms and methods, , Volume: 25, Issue:4		2015
Genotoxicity of quinocetone, cyadox and olaquindox in vitro and in vivo.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, , Volume: 59		2013
Quinocetone triggers oxidative stress and induces cytotoxicity and genotoxicity in human peripheral lymphocytes of both genders.
Journal of the science of food and agriculture, , Volume: 93, Issue:6		2013
Investigation of quinocetone-induced genotoxicity in HepG2 cells using the comet assay, cytokinesis-block micronucleus test and RAPD analysis.
Toxicology in vitro : an international journal published in association with BIBRA, , Volume: 23, Issue:7		2009
Investigation of the genotoxicity of quinocetone, carbadox and olaquindox in vitro using Vero cells.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, , Volume: 47, Issue:2		2009

Pharmacokinetics (3)

ArticleYear
Physiologically based pharmacokinetic model for quinocetone in pigs and extrapolation to mequindox.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, , Volume: 34, Issue:2		2017
Comparative pharmacokinetics and tissue distribution of quinocetone in crucian carp (Carassius auratus), common carp (Cyprinus carpio L.), and grass carp (Ctenopharyngodon idella) following the same experimental conditions.
Journal of veterinary pharmacology and therapeutics, , Volume: 38, Issue:4		2015
Investigation of the ultrasound effect and target analyte selectivity of dispersive liquid-liquid microextraction and its application to a quinocetone pharmacokinetic study.
Journal of chromatography. A, , Dec-14, Volume: 1268		2012

Bioavailability (1)

ArticleYear
Comparative pharmacokinetics and tissue distribution of quinocetone in crucian carp (Carassius auratus), common carp (Cyprinus carpio L.), and grass carp (Ctenopharyngodon idella) following the same experimental conditions.
Journal of veterinary pharmacology and therapeutics, , Volume: 38, Issue:4		2015

Dosage (2)

ArticleYear
Toxicologic effect and transcriptome analysis for short-term orally dosed enrofloxacin combined with two veterinary antimicrobials on rat liver.
Ecotoxicology and environmental safety, , Sep-01, Volume: 220		2021
Comparative pharmacokinetics and tissue distribution of quinocetone in crucian carp (Carassius auratus), common carp (Cyprinus carpio L.), and grass carp (Ctenopharyngodon idella) following the same experimental conditions.
Journal of veterinary pharmacology and therapeutics, , Volume: 38, Issue:4		2015

Interactions (2)

ArticleYear
Toxicologic effect and transcriptome analysis for short-term orally dosed enrofloxacin combined with two veterinary antimicrobials on rat liver.
Ecotoxicology and environmental safety, , Sep-01, Volume: 220		2021
Molecularly imprinted solid-phase extraction combined with high-performance liquid chromatography for analysis of trace olaquindox residues in chick feeds.
Journal of the science of food and agriculture, , Volume: 91, Issue:13		2011