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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:10:17 UTC
HMDB IDHMDB0014752
Secondary Accession Numbers
  • HMDB0029753
  • HMDB14752
  • HMDB29753
Metabolite Identification
Common NameFurazolidone
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 Furoxone and by GlaxoSmithKline as Dependal-M. Furoxone 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.
Structure
Thumb
Synonyms
ValueSource
3-(5'-nitrofurfuralamino)-2-OxazolidoneChEBI
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinoneChEBI
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidoneChEBI
3-[(5-Nitrofurylidene)amino]-2-oxazolidoneChEBI
3-{[(5-nitro-2-furanyl)methylene]amino}-2-oxazolidinoneChEBI
5-nitro-N-(2-oxo-3-Oxazolidinyl)-2-furanmethanimineChEBI
FurazolidonaChEBI
FurazolidonumChEBI
FuroxoneChEBI
FZLChEBI
N-(5-nitro-2-Furfurylidene)-3-amino-2-oxazolidoneChEBI
N-(5-nitro-2-Furfurylidene)-3-aminooxazolidine-2-oneChEBI
NitrofurazolidoneChEBI
NitrofurazolidonumChEBI
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
FurazolMeSH
Chemical FormulaC8H7N3O5
Average Molecular Weight225.16
Monoisotopic Molecular Weight225.038570337
IUPAC Name3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one
Traditional Namefurazolidone
CAS Registry Number67-45-8
SMILES
[O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of organic compounds known as nitrofurans. These are compounds containing a furan ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassNitrofurans
Direct ParentNitrofurans
Alternative Parents
Substituents
  • 2-nitrofuran
  • Oxazolidinone
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Oxacycle
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic cation
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.36 g/LNot Available
LogP0.9Not 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9610000000-ab960b06286d0ccd8c6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1390000000-6d4a20ff37556f08e13bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1390000000-3c18d9819c68dd1ecba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mj-9500000000-9e58b2b1f6fd5b9343c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2290000000-63a56a073d7d4f4cfd09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-9670000000-ddd3d4a03c2a3bc6ab9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-9000000000-58fd85feae000f4153ddView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00614 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00614 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00614
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000957
KNApSAcK IDNot Available
Chemspider ID4481255
KEGG Compound IDC07999
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5323714
PDB IDNot Available
ChEBI ID5195
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:1476092 ]
  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. [PubMed:6651278 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
References
  1. Timperio AM, Kuiper HA, Zolla L: Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases. Xenobiotica. 2003 Feb;33(2):153-67. [PubMed:12623758 ]
  2. Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. [PubMed:10543364 ]
  3. Hoogenboom LA, Tomassini O, Oorsprong MB, Kuiper HA: Use of pig hepatocytes to study the inhibition of monoamine oxidase by furazolidone. Food Chem Toxicol. 1991 Mar;29(3):185-91. [PubMed:2032659 ]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. Timperio AM, Kuiper HA, Zolla L: Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases. Xenobiotica. 2003 Feb;33(2):153-67. [PubMed:12623758 ]
  2. Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. [PubMed:10543364 ]
  3. Hoogenboom LA, Tomassini O, Oorsprong MB, Kuiper HA: Use of pig hepatocytes to study the inhibition of monoamine oxidase by furazolidone. Food Chem Toxicol. 1991 Mar;29(3):185-91. [PubMed:2032659 ]