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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2013-02-09 00:31:41 UTC
HMDB IDHMDB14480
Secondary Accession NumbersNone
Metabolite Identification
Common NameNitrofurazone
DescriptionNitrofurazone is only found in individuals that have used or taken this drug. It 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. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis. [PubChem]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.
Structure
Thumb
Synonyms
  1. NFZ
  2. Nitrofurazan
Chemical FormulaC6H6N4O4
Average Molecular Weight198.1362
Monoisotopic Molecular Weight198.0389047
IUPAC Name[(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
Traditional IUPAC Name(E)-[(5-nitrofuran-2-yl)methylidene]aminourea
CAS Registry Number59-87-0
SMILES
NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O
InChI Identifier
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+
InChI KeyIAIWVQXQOWNYOU-FPYGCLRLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassFurans
Sub ClassNitrofurans
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Aldimine
  • Hydrazine Derivative
  • Imine
  • Nitro Compound
  • Organic Oxoazanium
  • Semicarbazide
  • Semicarbazone
Direct ParentNitrofurans
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Anti-Infective Agents, Urinary
  • Trypanocidal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point238 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.68e-01 g/LNot Available
LogP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.27 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
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00336
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00336
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00336
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4566720
KEGG Compound IDC08042
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitrofurazone
NuGOwiki LinkHMDB14480
Metagene LinkHMDB14480
METLIN IDNot Available
PubChem Compound5447130
PDB IDNFZ
ChEBI ID170239
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase 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
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
General function:
Involved in monooxygenase 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
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: 19934256