1.0 2014-09-11 05:14:52 UTC 2026-08-23 13:09:21 UTC T3D4752 Nitrofural SmallMolecule Nitrofural is an exogenous organic compound with the formula C6H6N4O4 and an average molecular weight of 198.14 g/mol. It exists as a solid at room temperature. Nitrofural belongs to the nitrofurans, a subclass of furans within the organic compounds. In terms of chemical classification, it is categorized as an organoheterocyclic compound. The compound functions as an industrial biocide. It has been recorded in five sources, including power cables in electrical and electronic equipment, processing fish in food and cookware, and household cleaning and consumer products such as tobacco pipes, pipe accessories, and non-electric simulated smoking devices. Regarding its biological activity, nitrofural acts as an inhibitor of two protein targets: glutathione reductase (gor) and the estrogen receptor (ESR1). Drug Household Toxin Synthetic Toxin Organic Compound Amine Drug Anti-Infective Agent Metabolite Household Toxin Synthetic Compound 5-Nitro-2-furaldehyde semicarbazone Furacilin Furacin Furaderm NFZ Nitrofural (Nitrofurazone) Nitrofurazan Nitrofurazone [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea C6H6N4O4 198.1362 198.0389047 [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea nitrofurazone 59-87-0 NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+ IAIWVQXQOWNYOU-FPYGCLRLSA-N Organic compounds Organoheterocyclic compounds Furans Nitrofurans Nitrofurans Carbonyl compounds Heteroaromatic compounds Hydrocarbon derivatives Nitroaromatic compounds Organic carbonic acids and derivatives Organic oxides Organic oxoazanium compounds Organic zwitterions Organopnictogen compounds Oxacyclic compounds Propargyl-type 1,3-dipolar organic compounds Semicarbazones 2-nitrofuran Allyl-type 1,3-dipolar organic compound Aromatic heteromonocyclic compound C-nitro compound Carbonic acid derivative Carbonyl group Heteroaromatic compound Hydrocarbon derivative Nitroaromatic compound Organic 1,3-dipolar compound Organic nitro compound Organic nitrogen compound Organic oxide Organic oxoazanium Organic oxygen compound Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Propargyl-type 1,3-dipolar organic compound Semicarbazide Semicarbazone Aromatic heteromonocyclic compounds Detected and Not Quantified Exogenous Cytoplasm Extracellular Membrane Nitrofurazone Drug Metabolism Pathway SMP0145314 Solid White powder. melting_point 238 dec°C solubility 210 mg/L (at 25°C) logp 0.23 logp 0.23 ALOGPS logs -2.87 ALOGPS solubility 2.68e-01 g/l ALOGPS logp -0.14 ChemAxon pka_strongest_acidic 11.79 ChemAxon pka_strongest_basic -2 ChemAxon iupac [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea ChemAxon average_mass 198.1362 ChemAxon mono_mass 198.0389047 ChemAxon smiles NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O ChemAxon formula C6H6N4O4 ChemAxon inchi InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+ ChemAxon inchikey IAIWVQXQOWNYOU-FPYGCLRLSA-N ChemAxon polar_surface_area 126.44 ChemAxon refractivity 45.21 ChemAxon polarizability 16.92 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Well absorbed. The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase. Rat LD₅₀ = 590 mg/kg Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules. Half Life: 5 hours Rat LD₅₀ = 590 mg/kg 3, not classifiable as to its carcinogenicity to humans. (L135) For the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f726cf05bf0> Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated. DB00336 HMDB14480 5447130 CHEMBL869 4566720 C08042 170239 NFZ Nitrofurazone International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php BE0000123 AC50 0.539 uM ACEA_T47D_80hr_Positive ACEA Biosciences BE0000298