Basic Info

Common NameNicarbazin(F05861)
2D Structure
FRCD IDF05861
CAS Number330-95-0
PubChem CID9507
FormulaC19H18N6O6
IUPAC Name

1,3-bis(4-nitrophenyl)urea;4,6-dimethyl-1H-pyrimidin-2-one

InChI Key

UKHWDRMMMYWSFL-UHFFFAOYSA-N

InChI

InChI=1S/C13H10N4O5.C6H8N2O/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22;1-4-3-5(2)8-6(9)7-4/h1-8H,(H2,14,15,18);3H,1-2H3,(H,7,8,9)

Canonical SMILES

CC1=CC(=NC(=O)N1)C.C1=CC(=CC=C1NC(=O)NC2=CC=C(C=C2)[N+](=O)[O-])[N+](=O)[O-]

Isomeric SMILES

CC1=CC(=NC(=O)N1)C.C1=CC(=CC=C1NC(=O)NC2=CC=C(C=C2)[N+](=O)[O-])[N+](=O)[O-]

Synonyms
        
            Nicarbasin
        
            Nicarbazin
        
            Nicarbazine
        
            330-95-0
        
            Nicrazin
        
            Nicrazine
        
            Nicarb
        
            Nicoxin
        
            Nirazin
        
            Nicarbazin [BAN]
        
Classifies
                

                  
                    Pesticide
                  
                    Veterinary Drug
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassN-phenylureas
Intermediate Tree NodesNot available
Direct ParentN-phenylureas
Alternative Parents
Molecular FrameworkNot available
SubstituentsN-phenylurea - Nitrobenzene - Nitroaromatic compound - Pyrimidone - Hydropyrimidine - Pyrimidine - Heteroaromatic compound - C-nitro compound - Carbonic acid derivative - Urea - Organic nitro compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Organic 1,3-dipolar compound - Organoheterocyclic compound - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Properties

Property NameProperty Value
Molecular Weight426.389
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Complexity582
Monoisotopic Mass426.129
Exact Mass426.129
Formal Charge0
Heavy Atom Count31
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count2

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Kidney Of ChickensUnited States4ppm
Skin Of ChickensUnited States4ppm
Liver Of ChickensUnited States4ppm
Muscle Of ChickensUnited States4ppm
Other Poultry Animals,Edible OffalJapan0.5ppm
Chicken,Edible OffalJapan0.5ppm
Other Poultry Animals,KidneyJapan0.5ppm
Other Poultry Animals,LiverJapan0.5ppm
Other Poultry Animals,FatJapan0.5ppm
Other Poultry Animals,MuscleJapan0.5ppm
Chicken,KidneyJapan0.2ppm
Chicken,LiverJapan0.2ppm
Chicken,FatJapan0.2ppm
Chicken,MuscleJapan0.2ppm

References

TitleJournalDatePubmed ID
Performance and anticoccidial effects of nicarbazin-fed broilers reared atstandard or reduced environmental temperatures.Poult Sci2017 Jun 128339759
Determination of the residue levels of nicarbazin and combinationnicarbazin-narasin in broiler chickens after oral administration.PLoS One2017 Jul 2728750013
A multi-residue method for 17 anticoccidial drugs and ractopamine in animaltissues by liquid chromatography-tandem mass spectrometry and time-of-flight massspectrometry.Drug Test Anal2016 May27443201
Feed additives diclazuril and nicarbazin in egg and liver samples from Croatianfarms.Food Addit Contam Part B Surveill201324779872
Development of a five-plex flow cytometric immunoassay for the simultaneousdetection of six coccidiostats in feed and eggs.Anal Bioanal Chem2012 Sep22850895
Determination of narasin and monensin in bovine, swine, and chicken tissues byliquid chromatography with tandem mass spectrometry: first action 2011.24.J AOAC Int2012 Jul-Aug22970563
Residues of veterinary medicinal products and coccidiostats in eggs--causes,control and results of surveillance program in Poland.Pol J Vet Sci201223390776
The efficacy of anticoccidial products against Eimeria spp. in northernbobwhites.Avian Dis2011 Mar21500637
Development and validation of an UPLC-MS/MS method for the determination ofionophoric and synthetic coccidiostats in vegetables.Anal Bioanal Chem2011 Dec21984012
Residue control of coccidiostats in food of animal origin in Poland during2007-2010.Food Addit Contam Part B Surveill201124786249
Veterinary pharmaceuticals and antibiotic resistance of Escherichia coli isolatesin poultry litter from commercial farms and controlled feeding trials.Poult Sci2010 Jan20008817
The effect of commonly used anticoccidials and antibiotics in a subclinicalnecrotic enteritis model.Avian Pathol2010 Feb20390538
Determination of veterinary pharmaceuticals in poultry litter and soil bymethanol extraction and liquid chromatography-tandem mass spectrometry.J Environ Sci Health B2009 Sep20183082
Validation of a multi-residue liquid chromatography-tandem mass spectrometryconfirmatory method for 10 anticoccidials in eggs according to CommissionDecision 2002/657/EC.J Chromatogr A2009 Nov 1319442981
Genotype comparison of sorbitol-negative Escherichia coli isolates from healthybroiler chickens from different commercial farms.Poult Sci2009 Jul19531720
Survey of the anticoccidial feed additive nicarbazin (as dinitrocarbanilideresidues) in poultry and eggs.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2008Jan17957540
Investigation of the causes for the occurrence of residues of the anticoccidialfeed additive nicarbazin in commercial poultry.Food Addit Contam2007 Sep17691005
Deposition and depletion of five anticoccidials in eggs.J Agric Food Chem2005 Sep 716131122
Incidence of residues of nine anticoccidials in eggs.Food Addit Contam2005 Nov16332635
The effect of cooking on veterinary drug residues in food: nicarbazin(dinitrocarbanilide component).Food Addit Contam2005 Nov16332636