ContaminantDB: Nicarbazin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:20:55 UTC

Update Date

2016-11-09 01:15:35 UTC

Accession Number

CHEM017439

Identification

Common Name

Nicarbazin

Class

Small Molecule

Description

Nicarbazin is a coccidiostat used on meat chickens. It is also used as a contraceptive for population control of Canada geese and feral pigeons.It is also a wide-spectrum anti-parasitic drug approved for veterinary use, effective on Toxocara canis, Toxascaris leonina, Ancylostoma caninum, Uncinaria stenocephala, Trichuris vulpis, Dipylidium caninum, and Taenia sp. and Mesocestoides sp.. Known brand names for specific countries include: Carbigran (the United States) Ceva Nicarbazin (South Africa) Cycarb (New Zealand) Keymix (Australia) Koffogran (South Africa) Kofozin (Israel) Nicarb 25% (the United States) Nicarbazin (Israel) Nicarbazin Elanco (the United States) Nicarbmax 100% (New Zealand) Nicarmix (the United States) Ovistop (Costa Rica and Italy) OvoControl (the United States) PhiCarb (Australia) R-12 (Belgium)From the chemical point of view, nicarbazin is an equimolar complex formed by 1,3 - bis (4- nitrophenyl) urea and 4-6 dimethyl-2- (1H) - pyrimidinone also called 4,4'-dinitrocarbanilide (DNC) and 2-hydroxy - 4,6 dimethylpyrimidine (HDP). The DNC represents the biologically active part of the complex, but to be absorbed it must be bound to the HDP. Because of its hydrophobic nature, the DNC alone is poorly absorbed and has a limited "biological availability" so, following oral administration, it would be eliminated without being absorbed. The DNC therefore requires HDP to be absorbed and to reach a plasma level that allows an effect in the target species. Following oral administration, nicarbazin rapidly dissociates in vivo into its two HDP and DNC components, which follow different routes of excretion: 95% of HDP is rapidly eliminated with urine, while DNC remains longer and is eliminated predominantly with feces. Metabolism and depletion of the two components have been studied extensively with the use of carbon-14-labeled nicarbazin. Following oral administration, nicarbazin rapidly dissociates in vivo into its two components HDP and DNC, which are absorbed through the intestine, then passing into the blood, and following different routes of excretion. The HDP is excreted more rapidly than the DNC, mainly through the kidneys via the urine, while the DNC is absorbed more rapidly than the HDP and is excreted more slowly than the latter through the liver, via the faeces. No significant residue of either component is noticeable in any fabric after 7 days. DNC accumulates in eggs and normally the concentration of DNC in eggs is less than 5 ppm. The two components HDP and DNC do not undergo metabolism in vivo and in vitro, except for the formation of derivatives structurally similar to nitroaniline. However, this possibility appears extremely remote, achievable only in the laboratory, in particular chemical-physical conditions (high temperature in a strongly acid environment).Of the two components of the nicarbazin molecule, the DNC takes on a significance from a toxicological point of view as it remains longer in the body. The DNC molecule was therefore considered as a marker compound in residue studies.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Nicarbazine	MeSH
Nicarbazin	MeSH

Chemical Formula

C₁₉H₁₈N₆O₆

Average Molecular Mass

426.389 g/mol

Monoisotopic Mass

426.129 g/mol

CAS Registry Number

330-95-0

IUPAC Name

1,3-bis(4-nitrophenyl)urea; 4,6-dimethylpyrimidin-2-ol

Traditional Name

4,6-dimethylpyrimidin-2-ol; urea, N,N'-bis(4-nitrophenyl)-

SMILES

CC1=CC(C)=NC(O)=N1.O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O

InChI Identifier

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)

InChI Key

UKHWDRMMMYWSFL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

N-phenylureas

Direct Parent

N-phenylureas

Alternative Parents

Substituents

N-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

Molecular Framework

Not Available

External Descriptors

organic molecular entity (CHEBI:81725 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	2.48	ALOGPS
logP	3	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	132.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.7 m³·mol⁻¹	ChemAxon
Polarizability	28.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-8fa76670dc5fb60b5f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000900000-8fa76670dc5fb60b5f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000900000-8fa76670dc5fb60b5f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-f67e2e8250e49e5542f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000900000-f67e2e8250e49e5542f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0000900000-f67e2e8250e49e5542f7	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB11434

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Nicarbazin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

9507

Kegg Compound ID

C18389

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Nicarbazin (CHEM017439)

Structure for CHEM017439: Nicarbazin