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Identification
NameNitrofural
Accession NumberDB00336  (APRD00050)
Typesmall molecule
Groupsapproved
Description

A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
FuracilinNot AvailableNot Available
NitrofurazoneNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
FuracinNot Available
FuradermNot Available
Brand mixturesNot Available
Categories
CAS number59-87-0
WeightAverage: 198.1362
Monoisotopic: 198.0389047
Chemical FormulaC6H6N4O4
InChI KeyIAIWVQXQOWNYOU-FPYGCLRLSA-N
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+
IUPAC Name
[(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
SMILES
NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O
Mass Specshow(8.69 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassFurans
SubclassNitrofurans
Direct parentNitrofurans
Alternative parentsSemicarbazones; Hydrazones; Nitronic Acids; Aldimines; Nitro Compounds; Polyamines; Organic Oxoazanium Compounds
Substituentssemicarbazone; hydrazone; semicarbazide; nitronic acid; nitro compound; aldimine; polyamine; organic oxoazanium; amine; organonitrogen compound; imine
Classification descriptionThis compound belongs to the nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Pharmacology
IndicationFor the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
PharmacodynamicsNitrofurazone is a topical antibacterial agent indicated as an adjunctive therapy for second and third degree burns when resistance to other agents is a real or potential problem. Nitrofurazone is also indicated in skin grafting when bacterial contamination may cause graft rejection or donor site infection, especially in hospitals with a history of resistant bacteria.
Mechanism of actionThe 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.
AbsorptionWell absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules (Polnaszek et al., 1984; Kutcher & McCalla, 1984; McCalla 1979; McCalla et al., 1975).

Route of eliminationNot Available
Half life5 hours
ClearanceNot Available
ToxicityRat LD50 = 590 mg/kg; Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated.
Affected organisms
  • Gram negative and gram positive bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.5716
Blood Brain Barrier + 0.9214
Caco-2 permeable - 0.5694
P-glycoprotein substrate Non-substrate 0.7552
P-glycoprotein inhibitor I Non-inhibitor 0.9271
P-glycoprotein inhibitor II Non-inhibitor 0.9278
Renal organic cation transporter Non-inhibitor 0.9347
CYP450 2C9 substrate Non-substrate 0.769
CYP450 2D6 substrate Non-substrate 0.8326
CYP450 3A4 substrate Non-substrate 0.6211
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9379
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8418
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9287
Ames test AMES toxic 0.9234
Carcinogenicity Non-carcinogens 0.692
Biodegradation Not ready biodegradable 0.7708
Rat acute toxicity 2.5276 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9188
hERG inhibition (predictor II) Non-inhibitor 0.9311
Pharmacoeconomics
Manufacturers
  • Shire development inc
  • Sherwood medical co
  • Ambix laboratories div organics corp america
  • Lannett co inc
  • Perrigo new york inc
  • Taro pharmaceuticals usa inc
  • Wendt laboratories inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
DressingTopical
LiquidIntramuscular
OintmentTopical
PowderOral
PowderTopical
Powder, for solutionOral
SolutionIntrauterine
SolutionIntravenous
SolutionOral
SolutionTopical
TabletOral
Prices
Unit descriptionCostUnit
Nitrofurazone powder0.63USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point238 dec °CPhysProp
water solubility210 mg/L (at 25 °C)BEILSTEIN
logP0.23HANSCH,C ET AL. (1995)
pKa10SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility2.68e-01 g/lALOGPS
logP0.23ALOGPS
logP-0.14ChemAxon
logS-2.9ALOGPS
pKa (strongest acidic)11.79ChemAxon
pKa (strongest basic)-2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area126.44ChemAxon
rotatable bond count3ChemAxon
refractivity45.21ChemAxon
polarizability16.92ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00862
KEGG CompoundC08042
PubChem Compound5447130
PubChem Substance46506509
ChemSpider4566720
PharmGKBPA164754877
HETNFZ
Drug Product Database575011
Drugs.comhttp://www.drugs.com/cons/nitrofurazone-topical.html
WikipediaNitrofurazone
ATC CodesP01CC02S02AA02S01AX04D09AA03B05CA03D08AF01
AHFS Codes
  • 08:36.00
  • 40:28.08
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Pyruvate dehydrogenase [ubiquinone]

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Pyruvate dehydrogenase [ubiquinone] P07003 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Glutathione reductase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Glutathione reductase P06715 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Vega-Teijido M, Caracelli I, Zukerman-Schpector J: Conformational analyses and docking studies of a series of 5-nitrofuran- and 5-nitrothiophen-semicarbazone derivatives in three possible binding sites of trypanothione and glutathione reductases. J Mol Graph Model. 2006 Mar;24(5):349-55. Epub 2005 Nov 7. Pubmed

3. Malate dehydrogenase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Malate dehydrogenase P61889 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. [Citrate [pro-3S]-lyase] ligase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
[Citrate [pro-3S]-lyase] ligase P77390 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Enzymes

1. Xanthine dehydrogenase/oxidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Xanthine dehydrogenase/oxidase P47989 Details

References:

  1. Tatsumi K, Kitamura S, Yoshimura H: Reduction of nitrofuran derivatives by xanthine oxidase and microsomes. Isolation and identification of reduction products. Arch Biochem Biophys. 1976 Jul;175(1):131-7. Pubmed
  2. Kutcher WW, McCalla DR: Aerobic reduction of 5-nitro-2-furaldehyde semicarbazone by rat liver xanthine dehydrogenase. Biochem Pharmacol. 1984 Mar 1;33(5):799-805. Pubmed

2. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09