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Identification
NameNitrofural
Accession NumberDB00336  (APRD00050)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA 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
5-Nitro-2-furaldehyde semicarbazone
Furacilin
Furacin
Nitrofural
Nitrofurazone
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
FuracinNot Available
FuradermNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIX8XI70B5Z6
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
Pharmacology
IndicationFor the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Pyruvate dehydrogenase [ubiquinone]Proteinyes
inhibitor
Escherichia coli (strain K12)P07003 details
Glutathione reductaseProteinyes
inhibitor
Escherichia coli (strain K12)P06715 details
Malate dehydrogenaseProteinyes
inhibitor
Escherichia coli (strain K12)P61889 details
[Citrate [pro-3S]-lyase] ligaseProteinyes
inhibitor
Escherichia coli (strain K12)P77390 details
Related Articles
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
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Nitrofural can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Nitrofural can be decreased when combined with Amiodarone.Approved, Investigational
ArtemetherThe metabolism of Nitrofural can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Nitrofural can be decreased when combined with Atomoxetine.Approved
BetaxololThe metabolism of Nitrofural can be decreased when combined with Betaxolol.Approved
BupropionThe metabolism of Nitrofural can be decreased when combined with Bupropion.Approved
CelecoxibThe metabolism of Nitrofural can be decreased when combined with Celecoxib.Approved, Investigational
ChloroquineThe metabolism of Nitrofural can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Nitrofural can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Nitrofural can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Nitrofural can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Nitrofural can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Nitrofural can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Nitrofural can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Nitrofural can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Nitrofural can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Nitrofural can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Nitrofural can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Nitrofural can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Nitrofural can be decreased when combined with Cocaine.Approved, Illicit
DarifenacinThe metabolism of Nitrofural can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Nitrofural can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Nitrofural can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Nitrofural can be decreased when combined with Desipramine.Approved
DiphenhydramineThe metabolism of Nitrofural can be decreased when combined with Diphenhydramine.Approved
DronedaroneThe metabolism of Nitrofural can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Nitrofural can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Nitrofural can be decreased when combined with Eliglustat.Approved
FluoxetineThe metabolism of Nitrofural can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Nitrofural can be decreased when combined with Fluvoxamine.Approved, Investigational
HaloperidolThe metabolism of Nitrofural can be decreased when combined with Haloperidol.Approved
ImipramineThe metabolism of Nitrofural can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Nitrofural can be decreased when combined with Indinavir.Approved
IsoniazidThe metabolism of Nitrofural can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Nitrofural can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Nitrofural can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Nitrofural can be decreased when combined with Lorcaserin.Approved
LumefantrineThe metabolism of Nitrofural can be decreased when combined with Lumefantrine.Approved
MethadoneThe metabolism of Nitrofural can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Nitrofural can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Nitrofural can be decreased when combined with Metoprolol.Approved, Investigational
MirabegronThe metabolism of Nitrofural can be decreased when combined with Mirabegron.Approved
NevirapineThe metabolism of Nitrofural can be decreased when combined with Nevirapine.Approved
NicardipineThe metabolism of Nitrofural can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Nitrofural can be decreased when combined with Nilotinib.Approved, Investigational
PanobinostatThe serum concentration of Nitrofural can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Nitrofural can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Nitrofural can be decreased when it is combined with Peginterferon alfa-2b.Approved
PromazineThe metabolism of Nitrofural can be decreased when combined with Promazine.Approved, Vet Approved
QuinidineThe metabolism of Nitrofural can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Nitrofural can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Nitrofural can be decreased when combined with Ranolazine.Approved, Investigational
RitonavirThe metabolism of Nitrofural can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Nitrofural can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Nitrofural can be decreased when combined with Ropinirole.Approved, Investigational
SertralineThe metabolism of Nitrofural can be decreased when combined with Sertraline.Approved
StiripentolThe metabolism of Nitrofural can be decreased when combined with Stiripentol.Approved
TerbinafineThe metabolism of Nitrofural can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe metabolism of Nitrofural can be decreased when combined with Thioridazine.Approved
TiclopidineThe metabolism of Nitrofural can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Nitrofural can be decreased when combined with Tipranavir.Approved, Investigational
TranylcypromineThe metabolism of Nitrofural can be decreased when combined with Tranylcypromine.Approved
VenlafaxineThe metabolism of Nitrofural can be decreased when combined with Venlafaxine.Approved
ZiprasidoneThe metabolism of Nitrofural can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD08AF01S01AX04S02AA02B05CA03D09AA03P01CC02
AHFS Codes
  • 08:36.00
  • 40:28.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.8 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5716
Blood Brain Barrier+0.9214
Caco-2 permeable-0.5694
P-glycoprotein substrateNon-substrate0.7552
P-glycoprotein inhibitor INon-inhibitor0.9271
P-glycoprotein inhibitor IINon-inhibitor0.9278
Renal organic cation transporterNon-inhibitor0.9347
CYP450 2C9 substrateNon-substrate0.769
CYP450 2D6 substrateNon-substrate0.8326
CYP450 3A4 substrateNon-substrate0.6211
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9379
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8418
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9287
Ames testAMES toxic0.9234
CarcinogenicityNon-carcinogens0.692
BiodegradationNot ready biodegradable0.7708
Rat acute toxicity2.5276 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9188
hERG inhibition (predictor II)Non-inhibitor0.9311
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 formsNot Available
Prices
Unit descriptionCostUnit
Nitrofurazone powder0.63USD g
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 Solubility0.268 mg/mLALOGPS
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 Area126.44 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.21 m3·mol-1ChemAxon
Polarizability16.92 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.69 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0pb9-9500000000-c26d5be0126e0a0e8278View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrofurans. These are compounds containing a furan ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassNitrofurans
Direct ParentNitrofurans
Alternative Parents
Substituents
  • 2-nitrofuran
  • Semicarbazone
  • Heteroaromatic compound
  • Semicarbazide
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Thiamine pyrophosphate binding
Specific Function:
Not Available
Gene Name:
poxB
Uniprot ID:
P07003
Molecular Weight:
62010.845 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Nadp binding
Specific Function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
gor
Uniprot ID:
P06715
Molecular Weight:
48772.195 Da
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:17139284 ]
  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:17016423 ]
  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:16275032 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Oxidoreductase activity
Specific Function:
Catalyzes the reversible oxidation of malate to oxaloacetate.
Gene Name:
mdh
Uniprot ID:
P61889
Molecular Weight:
32337.065 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
N-acetyltransferase activity
Specific Function:
Acetylation of prosthetic group (2-(5''-phosphoribosyl)-3'-dephosphocoenzyme-A) of the gamma subunit of citrate lyase.
Gene Name:
citC
Uniprot ID:
P77390
Molecular Weight:
40076.805 Da
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:17139284 ]
  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:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xanthine oxidase activity
Specific Function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular Weight:
146422.99 Da
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:952514 ]
  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:6585203 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23