Olaquindox

Basic Info

Common NameOlaquindox(F06064)
2D Structure
FRCD IDF06064
CAS Number23696-28-8
PubChem CID71905
FormulaC12H13N3O4
IUPAC Name

N-(2-hydroxyethyl)-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide

InChI Key

TURHTASYUMWZCC-UHFFFAOYSA-N

InChI

InChI=1S/C12H13N3O4/c1-8-11(12(17)13-6-7-16)15(19)10-5-3-2-4-9(10)14(8)18/h2-5,16H,6-7H2,1H3,(H,13,17)

Canonical SMILES

CC1=C([N+](=O)C2=CC=CC=C2N1[O-])C(=O)NCCO

Isomeric SMILES

CC1=C([N+](=O)C2=CC=CC=C2N1[O-])C(=O)NCCO

Synonyms
        
            Olaquindox
        
            23696-28-8
        
            Bisergon
        
            Bayernox
        
            Bayonox
        
            Olachindox
        
            2-((2-Hydroxyethyl)carbamoyl)-3-methylquinoxaline 1,4-dioxide
        
            N-(2-Hydroxyethyl)-3-methyl-2-quinoxalinecarboxamide 1,4-dioxide
        
            2-Quinoxalinecarboxamide, N-(2-hydroxyethyl)-3-methyl-, 1,4-dioxide
        
            NSC634933
Classifies
                

                  
                    Veterinary Drug
                  
                    Illegal Additives
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDiazanaphthalenes
SubclassBenzodiazines
Intermediate Tree NodesNot available
Direct ParentQuinoxalines
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAlpha-amino acid or derivatives - Quinoxaline - N-acylethanolamine - Benzenoid - Vinylogous amide - Carboxamide group - Secondary carboxylic acid amide - Alkanolamine - Carboxylic acid derivative - Organic oxoazanium - Azacycle - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Aminoxide - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic zwitterion - Carbonyl group - Organic oxygen compound - Alcohol - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Properties

Property NameProperty Value
Molecular Weight263.253
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Complexity421
Monoisotopic Mass263.091
Exact Mass263.091
XLogP-0.2
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,MuscleJapan0.3ppm
Other Poultry Animals,Edible OffalJapan0.3ppm
Chicken,Edible OffalJapan0.3ppm
Other Poultry Animals,KidneyJapan0.3ppm
Chicken,KidneyJapan0.3ppm
Other Poultry Animals,LiverJapan0.3ppm
Chicken,LiverJapan0.3ppm
Other Poultry Animals,FatJapan0.3ppm
Chicken,FatJapan0.3ppm
Chicken,MuscleJapan0.3ppm
Pig,Edible OffalJapan0.3ppm
Pig,KidneyJapan0.3ppm
Pig,LiverJapan0.3ppm
Pig,FatJapan0.3ppm
Pig,MuscleJapan0.3ppm

References

TitleJournalDatePubmed ID
Determination of olaquindox, carbadox and cyadox in animal feeds byultra-performance liquid chromatography tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Jul29642753
Acute and Subacute toxicity study of Olaquindox by feeding to common carp (Cyprinus carpio L.).Ecotoxicol Environ Saf2018 Jun 829890435
Critical role of p21 on olaquindox-induced mitochondrial apoptosis and S-phasearrest involves activation of PI3K/AKT and inhibition of Nrf2/HO-1pathway.Food Chem Toxicol2017 Oct28757460
GADD45a Regulates Olaquindox-Induced DNA Damage and S-Phase Arrest in HumanHepatoma G2 Cells via JNK/p38 Pathways.Molecules2017 Jan 1328098804
Simultaneous determination of five quinoxaline-1,4-dioxides in animal feeds usingan immunochromatographic strip.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201626666867
In vivo studies to highlight possible illegal treatments of rabbits with carbadoxand olaquindox.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201526400201
Evolution and dissemination of OqxAB-like efflux pumps, an emerging quinoloneresistance determinant among members of Enterobacteriaceae.Antimicrob Agents Chemother201525801572
A physiologically based pharmacokinetic model for the prediction of the depletionof methyl-3-quinoxaline-2-carboxylic acid, the marker residue of olaquindox, inthe edible tissues of pigs.J Vet Pharmacol Ther2014 Feb23631588
A sensitive and specific ELISA for determining a residue marker of threequinoxaline antibiotics in swine liver.Anal Bioanal Chem2013 Mar23354571
First detection of oqxAB in Salmonella spp. isolated from food.Antimicrob Agents Chemother2013 Jan23147728
Two generation reproduction and teratogenicity studies of feeding quinocetone fedto Wistar rats.Food Chem Toxicol2012 May22248866
Multiple spectroscopic studies on the interaction between olaquindox, a feedadditive, and bovine serum albumin.Food Chem Toxicol2012 Jul22525866
Mass spectrometric analysis of muscle samples to detect potential antibioticgrowth promoter misuse in broiler chickens.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222784097
Development of a lateral flow colloidal gold immunoassay strip for the rapiddetection of olaquindox residues.J Agric Food Chem2011 Sep 1421834531
Molecularly imprinted solid-phase extraction combined with high-performanceliquid chromatography for analysis of trace olaquindox residues in chick feeds.J Sci Food Agric2011 Oct21674504
Two generation reproduction and teratogenicity studies of feeding cyadox inWistar rats.Food Chem Toxicol2011 May21266187
A chronic toxicity study of cyadox in Wistar rats.Regul Toxicol Pharmacol2011 Mar21129430
The metabolism of olaquindox in rats, chickens and pigs.Toxicol Lett2011 Jan 1520974235
In vitro biotransformation and investigation of metabolic enzymes possiblyresponsible for the metabolism of bisdesoxyolaquindox in the liver fractions ofrats, chicken, and pigs.Toxicology2011 Jan 1120955753
The metabolism and N-oxide reduction of olaquindox in liver preparations of rats,pigs and chicken.Toxicol Lett2010 May 1920219653