Nicarbazin

Nicarbazin
Names
	IUPAC name 1,3-bis(4-nitrophenyl)urea; 4,6-dimethyl-1H-pyrimidin-2-one
Identifiers
CAS Number	330-95-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL95855 ;
ChemSpider	9135 ;
ECHA InfoCard	100.005.782
PubChem CID	9507;
UNII	11P9NUA12U ;
	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) Key: UKHWDRMMMYWSFL-UHFFFAOYSA-N ; InChI=1/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) Key: UKHWDRMMMYWSFL-UHFFFAOYAE;
	SMILES O=C1/N=C(\C=C(/N1)C)C.[O-][N+](=O)c1ccc(cc1)NC(=O)Nc2ccc([N+]([O-])=O)cc2;
Properties
Chemical formula	C19H18N6O6
Molar mass	426.38 g/mol
Appearance	light yellow powder
Density	0.5 g/mL
Melting point	265-275 C
Solubility in water	slightly soluble in dimethylsulphoxide (DMSO) and dimethylformamide (DMF); insoluble in water and methanol
Pharmacology
ATCvet code	QP51AE03 (WHO)
Hazards
	Lethal dose or concentration (LD, LC):
LC50 (median concentration)	>0.147 mg/L in rats
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Nicarbazin is a coccidiostat used on meat chickens. It is also used as a contraceptive for population control of Canada geese and feral pigeons.^[1]^[2]

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 ^[3]:

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)

References

↑ "US EPA - Nicarbazin Conditional Registration" (PDF). November 2005. Retrieved 27 August 2015.
↑ Danaher, M.; Campbell, K.; O'Keeffe, M.; Capurro, E.; Kennedy, G.; Elliott, C. T. (2008). "Survey of the anticoccidial feed additive nicarbazin (as dinitrocarbanilide residues) in poultry and eggs". Food Additives & Contaminants: Part A. 25 (1): 32–40. doi:10.1080/02652030701552956. PMID 17957540.
↑ Drugs.com https://www.drugs.com/international/nicarbazin.html. Retrieved 26 June 2017. Missing or empty |title= (help)

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[1] "US EPA - Nicarbazin Conditional Registration" (PDF). November 2005. Retrieved 27 August 2015.

[2] Danaher, M.; Campbell, K.; O'Keeffe, M.; Capurro, E.; Kennedy, G.; Elliott, C. T. (2008). "Survey of the anticoccidial feed additive nicarbazin (as dinitrocarbanilide residues) in poultry and eggs". Food Additives & Contaminants: Part A. 25 (1): 32–40. doi:10.1080/02652030701552956. PMID 17957540.

[Nicarbazin-3] Drugs.com https://www.drugs.com/international/nicarbazin.html. Retrieved 26 June 2017. Missing or empty |title= (help)