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targets (4) enzymes (2)
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Identification
Name Nitrofurazone
Accession Number DB00336 (APRD00050)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
NFZ
Nitrofurazan
Salts Not Available
Brand names
Name Company
Actin-N
Aldomycin
Alfucin
Amifur
Babrocid
Becafurazone
Biofuracina
Biofurea
Chemofuran
Chixin
Cocafurin
Coxistat
Dermofural
Dymazone
Dynazone
Eldezol
Eldezol F-6
Fedacin
Flavazone
Fracine
Furacilin
Furacillin
Furacin
Furacin Soluble Dressing
Furacin Topical Cream
Furacin Topical Solution
Furacin-E
Furacin-HC
Furacine
Furacinetten
Furacoccid
Furacort
Furacycline
Furaderm
Furagent
Furalcyn
Furaldon
Furalone
Furametral
Furan-Ofteno
Furaplast
Furaseptyl
Furaskin
Furatsilin
Furaziline
Furazin
Furazina
Furazol W
Furazone
Furazyme
Furesol
Furfurin
Furosem
Fuvacillin
Hemofuran
Ibiofural
Mammex
Mastofuran
Monafuracin
Monafuracis
Monofuracin
Nefco
NF-7
Nifucin
Nifurid
Nifuzon
Nitrofural
Nitrofuran
Nitrofurane
Nitrofurol
Nitrozone
Otofural
Otofuran
Sanfuran
Spray-Dermis
Spray-Foral
Vabrocid
Vadrocid
Yatrocin
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Brand mixtures Not Available
Categories
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Trypanocidal Agents
  • Anti-Infective Agents, Urinary
CAS number 59-87-0
Weight Average: 198.1362
Monoisotopic: 198.0389047
Chemical Formula C6H6N4O4
InChI Key InChIKey=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+
Plain Text
IUPAC Name
[(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
SMILES
NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O
Plain Text
Mass Spec show (8.69 KB)
Taxonomy
Kingdom Not Available
Classes
  • Nitrofurans
Substructures
  • Semicarbazones
  • Oxoazaniums
  • Nitro compounds
  • Carbamates and Derivatives
  • Nitrofurans
  • Heterocyclic compounds
  • Aromatic compounds
  • Semicarbazides
  • Hydrazine Derivatives
  • Furans
  • Imines
Pharmacology
Indication For the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
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.
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
Toxicity Rat 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
Pathways Not Available
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
Form Route Strength
Capsule Oral
Dressing Topical
Liquid Intramuscular
Ointment Topical
Powder Oral
Powder Topical
Powder, for solution Oral
Solution Intrauterine
Solution Intravenous
Solution Oral
Solution Topical
Tablet Oral
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Prices
Unit description Cost Unit
Nitrofurazone powder 0.63 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 238 dec °C PhysProp
water solubility 210 mg/L (at 25 °C) BEILSTEIN
logP 0.23 HANSCH,C ET AL. (1995)
pKa 10 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 2.68e-01 g/l ALOGPS
logP 0.23 ALOGPS
logP -0.14 ChemAxon
logS -2.9 ALOGPS
pKa (strongest acidic) 11.79 ChemAxon
pKa (strongest basic) -2 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 126.44 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 45.21 ChemAxon
polarizability 16.92 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00862 Link_out
KEGG Compound C08042 Link_out
PubChem Compound 5447130 Link_out
PubChem Substance 46506509 Link_out
ChemSpider 4566720 Link_out
PharmGKB PA164754877 Link_out
HET NFZ Link_out
Drug Product Database 575011 Link_out
Drugs.com http://www.drugs.com/cons/nitrofurazone-topical.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Nitrofurazone Link_out
ATC Codes
  • B05CA03
  • D08AF01
  • P01CC02
  • S02AA02
  • S01AX04
  • D09AA03
AHFS Codes
  • 08:36.00
  • 40:28.08
PDB Entries Not Available
FDA label Not Available
MSDS show (73.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Pyruvate dehydrogenase [cytochrome]

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P07003 Link_out
Gene: poxB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor

Maintains high levels of reduced glutathione in the cytosol

Organism class: bacterial
UniProt ID: P06715 Link_out
Gene: gor
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor

Catalyzes the reversible oxidation of malate to oxaloacetate

Organism class: bacterial
UniProt ID: P61889 Link_out
Gene: mdh
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor

Acetylation of prosthetic group (2-(5''-phosphoribosyl)- 3'-dephosphocoenzyme-A) of the gamma subunit of citrate lyase

Organism class: bacterial
UniProt ID: P77390 Link_out
Gene: citC
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

This enzyme can be converted from the dehydrogenase form (D) to the oxidase form (O) irreversibly by proteolysis or reversibly through the oxidation of sulfhydryl groups

UniProt ID: P47989 Link_out
Gene: XDH Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19