Furazolidone (CHEM016013)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:10:41 UTC
Update Date2016-11-09 01:15:19 UTC
Accession NumberCHEM016013
Identification
Common NameFurazolidone
ClassSmall Molecule
DescriptionFurazolidone is a nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone has been shown to exhibit antibiotic and anti-microbial functions (PMID 1476092, 6651278). Furazolidone is also used as a poultry food additive. It is marketed by Roberts Laboratories under the brand name Furazolidone and by GlaxoSmithKline as Dependal-M. Furazolidone has a broad antibacterial spectrum covering the majority of gastrointestinal tract pathogens including E. coli, staphylococci, Salmonella, Shigella, Proteus, Aerobacter aerogenes, Vibrio cholerae and Giardia lamblia. Its bactericidal activity is based upon its interference with DNA replication and protein production. Furazolidone binds bacterial DNA which leads to the gradual inhibition of monoamine oxidase (From Martindale, The Extra Pharmacopoeia, 30th ed, p514). Furazolidone and its related free radical products are believed to bind DNA and induce cross-links. Bacterial DNA is particularly susceptible to this drug leading to high levels of mutations (transitions and transversions) in the bacterial chromosome. Furazolidone belongs to the family of Nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
FuroxoneKegg
3-(5'-Nitrofurfuralamino)-2-oxazolidoneHMDB
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinoneHMDB
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidoneHMDB
3-[(5-Nitrofurylidene)amino]-2-oxazolidoneHMDB
3-{[(5-nitro-2-furanyl)methylene]amino}-2-oxazolidinoneHMDB
5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimineHMDB
FurazolidonaHMDB
FurazolidonumHMDB
FZLHMDB
N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidoneHMDB
N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-oneHMDB
NitrofurazolidoneHMDB
NitrofurazolidonumHMDB
3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinoneHMDB
3-((5-Nitrofurfurylidene)amino)-2-oxazolidinoneHMDB
3-((5-Nitrofurfurylidene)amino)-2-oxazolidoneHMDB
3-((5-Nitrofurfurylidine)amino)-2-oxazolidinoneHMDB
3-((5-Nitrofurylidene)amino)-2-oxazolidoneHMDB
3-(5-Nitrofurfurylideneamino)-2-oxazolidinoneHMDB
3-[(5-Nitrofurfurylidine)amino]-2-oxazolidinoneHMDB
3-[(e)-(5-Nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-oneHMDB
3-[[(5-Nitro-2-furanyl)methylene]-amino]-2-oxazolidinoneHMDB
3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinoneHMDB
3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone, 9ciHMDB
BifuronHMDB
CoriziumHMDB
CoryziumHMDB
DiafuronHMDB
EnterotoxonHMDB
Fiurox aerosol powderHMDB
FurallHMDB
FuraxonHMDB
FuraxoneHMDB
FurazolidineHMDB
FurazonHMDB
FuridonHMDB
FurovagHMDB
FuroxHMDB
FuroxalHMDB
FuroxaneHMDB
FuroxonHMDB
Furoxone swine mixHMDB
FurozolidineHMDB
GiardilHMDB
GiarlamHMDB
MedaronHMDB
NeftinHMDB
NicolenHMDB
NifulidoneHMDB
NifuranHMDB
NifurazolidoneHMDB
NitrofuroxonHMDB
OptazolHMDB
OrtazolHMDB
PuradinHMDB
RoptazolHMDB
SclaventerolHMDB
TikofuranHMDB
TopazoneHMDB
TrichofuronHMDB
TricofuronHMDB
TricoronHMDB
TrifuroxHMDB
USAF ea-1HMDB
ViofuragynHMDB
FurazolHMDB
Chemical FormulaC8H7N3O5
Average Molecular Mass225.160 g/mol
Monoisotopic Mass225.039 g/mol
CAS Registry Number67-45-8
IUPAC Name3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one
Traditional Namefurazolidone
SMILES[O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O
InChI IdentifierInChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2/b9-5+
InChI KeyPLHJDBGFXBMTGZ-WEVVVXLNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrofurans. Nitrofurans are compounds containing a furan ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassNitrofurans
Direct ParentNitrofurans
Alternative Parents
Substituents
  • Nitroaromatic compound
  • 2-nitrofuran
  • Oxazolidinone
  • Oxazolidine
  • Heteroaromatic compound
  • C-nitro compound
  • Carbonic acid derivative
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP0.15ALOGPS
logP0.87ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area98.18 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.08 m³·mol⁻¹ChemAxon
Polarizability19.78 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9610000000-ab960b06286d0ccd8c6cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1390000000-6d4a20ff37556f08e13bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1390000000-3c18d9819c68dd1ecba9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mj-9500000000-9e58b2b1f6fd5b9343c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2290000000-63a56a073d7d4f4cfd09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-9670000000-ddd3d4a03c2a3bc6ab9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9000000000-58fd85feae000f4153ddSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0014752
FooDB IDFDB000957
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFurazolidone
Chemspider ID4481255
ChEBI ID5195
PubChem Compound ID5323714
Kegg Compound IDC07999
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ivanics E, Glavits R, Bodi T, Toth E: Demonstration of Clostridium septicum infection in a goose flock. Acta Vet Hung. 1992;40(1-2):71-4.
2. Carlson JR, Thornton SA, DuPont HL, West AH, Mathewson JJ: Comparative in vitro activities of ten antimicrobial agents against bacterial enteropathogens. Antimicrob Agents Chemother. 1983 Oct;24(4):509-13.