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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 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
Data?1582753217
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 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
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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.36 g/LNot Available
LogP0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+142.34730932474
DeepCCS[M-H]-140.16730932474
DeepCCS[M-2H]-173.73430932474
DeepCCS[M+Na]+148.25830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Furazolidone[O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O2565.3Standard polar33892256
Furazolidone[O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O2132.0Standard non polar33892256
Furazolidone[O-][N+](=O)C1=CC=C(O1)\C=N\N1CCOC1=O2273.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Furazolidone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9610000000-ab960b06286d0ccd8c6c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Furazolidone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Furazolidone 10V, Positive-QTOFsplash10-004i-1390000000-6d4a20ff37556f08e13b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Furazolidone 20V, Positive-QTOFsplash10-004i-1390000000-3c18d9819c68dd1ecba92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Furazolidone 40V, Positive-QTOFsplash10-08mj-9500000000-9e58b2b1f6fd5b9343c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Furazolidone 10V, Negative-QTOFsplash10-00di-2290000000-63a56a073d7d4f4cfd092016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Furazolidone 20V, Negative-QTOFsplash10-0fk9-9670000000-ddd3d4a03c2a3bc6ab9e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Furazolidone 40V, Negative-QTOFsplash10-0fk9-9000000000-58fd85feae000f4153dd2016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00614 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00614 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000957
KNApSAcK IDNot Available
Chemspider ID4481255
KEGG Compound IDC07999
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFurazolidone
METLIN IDNot Available
PubChem Compound5323714
PDB IDNot Available
ChEBI ID5195
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]