Human Metabolome Database Version 3.5

Showing metabocard for Nitrofurazone (HMDB14480)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:49 -0600
Update Date 2013-02-08 17:31:41 -0700
HMDB ID HMDB14480
Secondary Accession Numbers None
Metabolite Identification
Common Name Nitrofurazone
Description Nitrofurazone 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
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Display: 2D Structure | 3D Structure
Synonyms
  1. NFZ
  2. Nitrofurazan
Chemical Formula C6H6N4O4
Average Molecular Weight 198.1362
Monoisotopic Molecular Weight 198.0389047
IUPAC Name [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
Traditional IUPAC Name (E)-[(5-nitrofuran-2-yl)methylidene]aminourea
CAS Registry Number 59-87-0
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 Key IAIWVQXQOWNYOU-FPYGCLRLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Furans
Sub Class Nitrofurans
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Aldimine
  • Hydrazine Derivative
  • Imine
  • Nitro Compound
  • Organic Oxoazanium
  • Semicarbazide
  • Semicarbazone
Direct Parent Nitrofurans
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 238 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.68e-01 g/L Not Available
LogP 0.2 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.27 g/L ALOGPS
LogP 0.23 ALOGPS
LogP -0.14 ChemAxon
LogS -2.87 ALOGPS
pKa (strongest acidic) 11.79 ChemAxon
pKa (strongest basic) -2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 126.44 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 45.21 ChemAxon
Polarizability 16.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00336
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00336
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00336 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 4566720 Link_out
KEGG Compound ID C08042 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Nitrofurazone Link_out
NuGOwiki Link HMDB14480 Link_out
Metagene Link HMDB14480 Link_out
METLIN ID Not Available
PubChem Compound 5447130 Link_out
PDB ID NFZ Link_out
ChEBI ID 170239 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Xanthine dehydrogenase/oxidase
Reactions: Not Available
Gene Name: XDH
Uniprot ID: P47989 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA