Carbadox

Basic Info

Common NameCarbadox(F05962)
2D Structure
FRCD IDF05962
CAS Number6804-07-5
PubChem CID5353472
FormulaC11H10N4O4
IUPAC Name

methyl N-[(E)-(1-hydroxy-4-oxidoquinoxalin-4-ium-2-ylidene)methyl]iminocarbamate

InChI Key

BPMVRAQIQQEBLN-OBPBNMOMSA-N

InChI

InChI=1S/C11H10N4O4/c1-19-11(16)13-12-6-8-7-14(17)9-4-2-3-5-10(9)15(8)18/h2-7,18H,1H3/b8-6+,13-12?

Canonical SMILES

COC(=O)N=NC=C1C=[N+](C2=CC=CC=C2N1O)[O-]

Isomeric SMILES

COC(=O)N=N/C=C/1\C=[N+](C2=CC=CC=C2N1O)[O-]

Synonyms
        
            MLS001333201
        
            CARBADOX
        
            6804-07-5
        
            UNII-M2X04R2E2Y
        
            Getroxel
        
            Mecadox
        
            M2X04R2E2Y
        
            GS-6244
        
            SMR000857182
        
            DSSTox_CID_23913
Classifies
                

                  
                    Veterinary Drug
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
SubstituentsQuinoxaline - 1-hydroxylamino, 4-unsubstituted benzenoid - 1-hydroxylamino, 2-unsubstituted benzenoid - Benzenoid - Azo compound - Nitrone - Carbonic acid derivative - Azacycle - N-organohydroxylamine - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Hydrocarbon derivative - Organic zwitterion - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - 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 Weight262.225
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Complexity446
Monoisotopic Mass262.07
Exact Mass262.07
XLogP0.3
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Liver Of SwineUnited States30ppb

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
Bacterial Whack-a-Mole: Reconsidering the Public Health Relevance of UsingCarbadox in Food Animals.MBio2017 Sep 2628951481
The In-Feed Antibiotic Carbadox Induces Phage Gene Transcription in the Swine GutMicrobiome.MBio2017 Aug 828790203
Further investigations into the genotoxicity of quinoxaline-di-N-oxides and theirprimary metabolites.Food Chem Toxicol2016 Jul27170491
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
The agricultural antibiotic carbadox induces phage-mediated gene transfer in Salmonella.Front Microbiol201424575089
Simultaneous screening analysis of 3-methyl-quinoxaline-2-carboxylic acid andquinoxaline-2-carboxylic acid residues in edible animal tissues by a competitive indirect immunoassay.J Agric Food Chem2013 Oct 2324090030
A sensitive and specific ELISA for determining a residue marker of threequinoxaline antibiotics in swine liver.Anal Bioanal Chem2013 Mar23354571
Simultaneous determination of quinoxaline-1,4-dioxides in feeds using molecularlyimprinted solid-phase extraction coupled with HPLC.J Sep Sci2013 Jan23335457
Genotoxicity evaluation of Mequindox in different short-term tests.Food Chem Toxicol2013 Jan23063596
Controlling Salmonella infection in weanling pigs through water delivery ofdirect-fed microbials or organic acids. Part I: effects on growth performance,microbial populations, and immune status.J Anim Sci2012 Jan21841080
Effect of dietary acids on growth performance of nursery pigs: a cooperativestudy.J Anim Sci2012 Dec23100581
Development and validation of an immunochromatographic assay for the rapiddetection of quinoxaline-2-carboxylic acid, the major metabolite of carbadox inthe edible tissues of pigs.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222423958
Development and validation of an indirect competitive enzyme-linked immunosorbentassay for monitoring quinoxaline-2-carboxylic acid in the edible tissues ofanimals.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Nov21827237
Antibiotics in feed induce prophages in swine fecal microbiomes.MBio2011 Nov 2922128350
Growth performance and gastrointestinal microbial ecology responses of pigletsreceiving Saccharomyces cerevisiae fermentation products after an oral challenge with Escherichia coli (K88).J Anim Sci2011 Apr21148775
The effects of dietary additives on faecal levels of Lactobacillus spp.,coliforms, and Escherichia coli, and faecal prevalence of Salmonella spp. andCampylobacter spp. in US production nursery swine.J Appl Microbiol2010 Jan19614855
Effect of supplementing zinc oxide and biotin with or without carbadox on nurserypig performance.J Anim Sci2009 Oct19574566
Investigation of the genotoxicity of quinocetone, carbadox and olaquindox invitro using Vero cells.Food Chem Toxicol2009 Feb19061932