Nitrofural

Identification

Summary

Nitrofural is a topical antibacterial for the prevention and treatment of bacterial infections of the skin.

Generic Name
Nitrofural
DrugBank Accession Number
DB00336
Background

Nitrofural or nitrofurazone is a topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofural has also been administered orally in the treatment of trypanosomiasis.

Except for topical drug products formulated for dermatologic application, the FDA withdrew its approval for the use of drug products containing nitrofurazone.1

Type
Small Molecule
Groups
Approved, Investigational, Vet approved, Withdrawn
Structure
Weight
Average: 198.1362
Monoisotopic: 198.0389047
Chemical Formula
C6H6N4O4
Synonyms
  • 5-Nitro-2-furaldehyde semicarbazone
  • Furacilin
  • Nitrofural
  • Nitrofurazone

Pharmacology

Indication

For the treatment of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofSkin infections•••••••••••••••••• ••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Nitrofurazone 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 action

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.

TargetActionsOrganism
AGlutathione reductase
inhibitor
Escherichia coli (strain K12)
Absorption

Well absorbed.

Volume of distribution

Not Available

Protein binding

Not 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 elimination

Not Available

Half-life

5 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Rat LD50 = 590 mg/kg; Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Furacin / Furaderm / Nitrofurazone
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ขี้ผึ้งแบ็คตาซินOintment0.2 %w/wTopicalบริษัท โอสถ อินเตอร์ แลบบอราทอรีส์ จำกัด จำกัด1988-08-09Not applicableThailand flag
ขี้ผึ้งโพลีซินOintment0.2 %w/wTopicalบริษัท แอดวานซ์ ฟาร์มาซูติคอล แมนูเฟคเจอริ่ง จำกัด2014-02-06Not applicableThailand flag
ฟูโซน ออยเมนท์Ointment0.2 %w/wTopicalบริษัท เอเชี่ยนยูเนี่ยนแล็บบอราตอรี่ จำกัด จำกัด1987-05-22Not applicableThailand flag
เดนซ่า ครีมCream0.2 %w/wบริษัท สยามเภสัช จำกัด2010-03-30Not applicableThailand flag
ไมโตรซินOintment0.2 %w/wTopicalบริษัท โรงงานเภสัชกรรม เกร๊ทเตอร์ฟาร์ม่า จำกัด จำกัด2013-10-302020-09-29Thailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FURADERM % 0,2 56 GR POMADNitrofural (0.2 %)OintmentTopicalTOPRAK İLAÇ VE KİMYEVİ MADDELER SAN.VE TİC. A.Ş.2013-01-29Not applicableTurkey flag

Categories

ATC Codes
B05CA03 — NitrofuralS02AA02 — NitrofuralD08AF01 — NitrofuralD09AA03 — NitrofuralS01AX04 — NitrofuralP01CC02 — Nitrofural
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Furans
Sub Class
Nitrofurans
Direct Parent
Nitrofurans
Alternative Parents
Nitroaromatic compounds / Semicarbazones / Heteroaromatic compounds / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Organic oxoazanium compounds / Organopnictogen compounds / Organic zwitterions / Organic oxides
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Substituents
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
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Gram negative and gram positive bacteria

Chemical Identifiers

UNII
X8XI70B5Z6
CAS number
59-87-0
InChI Key
IAIWVQXQOWNYOU-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

References

General References
  1. Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
Human Metabolome Database
HMDB0014480
KEGG Drug
D00862
KEGG Compound
C08042
PubChem Compound
5447130
PubChem Substance
46506509
ChemSpider
4566720
BindingDB
50420350
RxNav
7455
ChEMBL
CHEMBL869
ZINC
ZINC000000897369
PharmGKB
PA164754877
PDBe Ligand
NFZ
Drugs.com
Drugs.com Drug Page
Wikipedia
Nitrofurazone
PDB Entries
1yki / 3r6w
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
0TerminatedTreatmentOsteomyelitis1

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
  • Gallipot
  • Pharmedix
  • Taro Pharmaceuticals USA
Dosage Forms
FormRouteStrength
InsertVaginal
OintmentTopical
SolutionTopical0.2 g
OintmentTopical0.2 %
OintmentTopical0.2 g
Solution / dropsAuricular (otic)20 ml
SolutionOphthalmic0.02 %
SuppositoryVaginal
InsertVaginal6 mg
OintmentTopical2 %
OintmentTopical200 mg
InsertVaginal6.000 mg
OintmentTopical0.2 %w/w
LiquidAuricular (otic)2 mg/1g
Cream0.2 %w/w
Prices
Unit descriptionCostUnit
Nitrofurazone powder0.63USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)238 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 Area123.76 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity44.21 m3·mol-1Chemaxon
Polarizability16.97 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (8.69 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00dl-6900000000-ab197de8a008fa662f84
Mass Spectrum (Electron Ionization)MSsplash10-0pb9-9500000000-c26d5be0126e0a0e8278
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-144.7348122
predicted
DarkChem Lite v0.1.0
[M-H]-143.8774222
predicted
DarkChem Lite v0.1.0
[M-H]-145.0733122
predicted
DarkChem Lite v0.1.0
[M-H]-129.65858
predicted
DeepCCS 1.0 (2019)
[M+H]+144.6188122
predicted
DarkChem Lite v0.1.0
[M+H]+148.9267434
predicted
DarkChem Lite v0.1.0
[M+H]+144.6238122
predicted
DarkChem Lite v0.1.0
[M+H]+132.91862
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.3505122
predicted
DarkChem Lite v0.1.0
[M+Na]+144.3073122
predicted
DarkChem Lite v0.1.0
[M+Na]+144.2137122
predicted
DarkChem Lite v0.1.0
[M+Na]+141.05367
predicted
DeepCCS 1.0 (2019)

Targets

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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
Uniprot Name
Glutathione reductase
Molecular Weight
48772.195 Da
References
  1. 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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:24