Compound: Nicarbazin
SMILES: O=[N+]([O-])c1ccc(NC(=O)Nc2ccc([N+](=O)[O-])cc2)cc1.O=c1nc(cc([nH]1)C)C
InChIKey: UKHWDRMMMYWSFL-UHFFFAOYSA-N
Synonyms: Nicarbazin, 330-95-0, Nicarbazine, Nirazin, Nicoxin, Nicrazin, Nicrazine, Nicarb, Nicarbasin, MK 75, 11P9NUA12U, NSC-7171, Nicarmix 25, Nicarb 25%, RefChem:57682, Carbigran 25, Nicarbazin, 206-359-1, AI3-60130, DTXSID6034762, 1,3-bis(4-nitrophenyl)urea;4,6-dimethyl-1H-pyrimidin-2-one, 1,3-Bis(4-nitrophenyl)urea 4,6-dimethylpyrimidin-2-ol (1:1), Nicarbazin [BAN], n,n'-bis(4-nitrophenyl)urea compound with 4,6-dimethyl-2-pyrimidinone, N,N inverted exclamation marka-Bis(4-nitrophenyl)urea compd. with 4,6-dimethyl-2-pyrimidinol (1:1), MK 75 (VAN), HSDB 7466, NSC 7171, EINECS 206-359-1, UNII-11P9NUA12U, Nicarbazin; 1,3-Bis(4-nitrophenyl)urea 4,6-dimethylpyrimidin-2-ol; Nicarbazine, C19H18N6O6, MFCD00867204, 4,4'-Dinitrocarbanilide, 4,6-dimethyl-2-pyrimidinol, Nicarbazin (Standard), NICARBAZIN [MI], 1,3-bis(4-nitrophenyl)urea,4,6-dimethyl-1H-pyrimidin-2-one, NICARBAZIN [HSDB], NICARBAZIN [MART.], CHEMBL95855, SCHEMBL578675, SCHEMBL578676, orb1304522, orb3025277, NICARBAZIN [GREEN BOOK], 1,3-Bis(4-nitrophenyl)urea-4,6-dimethylpyrimidin-2-ol, DTXCID4014762, CHEBI:81725, 4, 4,6-dimethyl-2-pyrimidinol, MSK7109, NSC7171, UKHWDRMMMYWSFL-UHFFFAOYSA-N, HMS5083N16, MSK7109-100AF, Tox21_304000, MFCD09033149, s4866, AKOS015900412, AKOS025310650, MSK7109-1000F, CCG-268958, HY-107814R, Urea, N,N-bis(4-nitrophenyl)-, compound with 4,6-dimethyl-2(1H)-pyrimidinone (1:1), NCGC00357219-01, Nicarbazin Solution in DMF, 1000ug/mL, AS-13365, CAS-330-95-0, FN158224, SY038632, HY-107814, CS-0030690, NS00079489, C18389, D95916, Nicarbazin, VETRANAL(TM), analytical standard, Nicarbazin Solution in Acetonitrile/DMF, 100ug/mL, Q2020694, 1,3-bis(4-nitrophenyl)urea; 4,6-dimethylpyrimidin-2-ol, 1,3-Bis-(4-nitro-phenyl)-urea and 4,6-Dimethyl-pyrimidin-2-ol, N,N'-Bis(4-nitrophenyl)urea--4,6-dimethylpyrimidin-2(1H)-one (1/1), 1,3-Bis(4-nitrophenyl)urea compd. with 4,6-dimethylpyrimidin-2(1H)-one(1:1)
Theoretical properties:
molecular_formula: C19H18N6O6
molecular_weight: 426.4 g/mol
exact_mass: 426.12878232 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 31
topological_polar_surface_area: 174 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 2
Physical properties:
physical_state: Crystals
color: Crystals
odor: Characteristic odor
melting_point: decomposes 265-275 °C
density: 0.5 g/ml
solubility: Practically insoluble in water. Complex is slowly decomposed by trituration with water, or more rapidly by dilute aqueous acids.
Descriptions:
{"pubchem": "Nicarbazin is an organic molecular entity.", "chebi": null, "chembl": "NICARBAZIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Nicarbazin is a coccidiostat used on meat chickens. It is also used as a contraceptive for population control of Canada geese and feral pigeons.\nIt 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:\n\nCarbigran (the United States)\nCeva Nicarbazin (South Africa)\nCycarb (New Zealand)\nKeymix (Australia)\nKoffogran (South Africa)\nKofozin (Israel)\nNicarb 25% (the United States)\nNicarbazin (Israel)\nNicarbazin Elanco (the United States)\nNicarbmax 100% (New Zealand)\nNicarmix (the United States)\nOvistop (Italy  and Costa Rica)\nOvoControl (the United States)\nPhiCarb (Australia)\nR-12 (Belgium)\nFrom the chemical point of view, nicarbazin is an equimolar complex formed by 1,3 - bis (4- nitrophenyl) urea and\u202f4-6\u202fdimethyl-2- (1H) - pyrimidinone also called 4,4'-dinitrocarbanilide (DNC) and 2-hydroxy - 4,6 dimethylpyrimidine (HDP).\nThe 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.\nFollowing 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.\nMetabolism 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.\nThe 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).\nOf 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."}