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Showing drug card for Furazolidone (DB00614)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:54
Primary Accession Number DB00614
Secondary Accession Number
  • APRD00988
Name Furazolidone
Drug Type
  • Approved
  • Small Molecule
Description A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone acts by gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)
Synonyms
  1. Nitrofurazolidone
  2. Nitrofurazolidonum
  3. USAF EA-1
Brand Names
  1. Bifuron
  2. Corizium
  3. Coryzium
  4. Diafuron
  5. Enterotoxon
  6. Fiurox aerosol powder
  7. Furall
  8. Furaxon
  9. Furaxone
  10. Furazol
  11. Furazolidine
  12. Furazolidon
  13. Furazon
  14. Furidon
  15. Furovag
  16. Furox
  17. Furoxal
  18. Furoxane
  19. Furoxon
  20. Furoxone
  21. Furoxone Liquid
  22. Furoxone Swine Mix
  23. Furozolidine
  24. Giardil
  25. Giarlam
  26. Medaron
  27. Neftin
  28. Nicolen
  29. Nifulidone
  30. Nifuran
  31. Nifurazolidone
  32. Nitrofuroxon
  33. Optazol
  34. Ortazol
  35. Puradin
  36. Roptazol
  37. Sclaventerol
  38. Tikofuran
  39. Topazone
  40. Trichofuron
  41. Tricofuron
  42. Tricoron
  43. Trifurox
  44. Viofuragyn
Brand Mixtures Not Available
Chemical IUPAC Name 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
Chemical Formula C8H7N3O5
Chemical Structure Structure
CAS Registry Number 67-45-8
InChI Identifier InChI=1/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2
InChI Key PLHJDBGFXBMTGZ-UHFFFAOYAA
KEGG Drug D00830 Link Image
KEGG Compound C07999 Link Image
PubChem Compound 3435 Link Image
PubChem Substance 10200 Link Image
ChEBI ID Not Available
PharmGKB ID PA449718 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00674761 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/furazol.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Furazolidone Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 225.1583
Monoisotopic Molecular Weight 225.0386
State Solid
Melting Point 255 oC
Experimental Water Solubility 40 mg/L Source: PhysProp
Predicted Water Solubility 3.64e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.9 Source: PhysProp
Predicted LogP 0.15 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.79 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES [O-][N+](=O)C1=CC=C(O1)/C=N/N1CCOC1=O
Canonical SMILES [O-][N+](=O)C1=CC=C(O1)C=NN1CCOC1=O
Drug Category
  • Anti-Infective Agents, Local
  • Anti-Infective Agents, Urinary
  • Antitrichomonal Agents
  • Monoamine Oxidase Inhibitors
ATC Codes
AHFS Codes Not Available
Indication For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.
Pharmacology 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; this antimicrobial action minimizes the development of resistant organisms.
Mechanism of Action 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.
Absorption Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration
Toxicity Reactions to Furoxone have been reported including a fall in blood pressure, urticaria, fever, arthralgia, and a vesicular morbilliform rash. Other adverse effects can include a brown discoloration of the urine; hemolysis can occur in G6PDH-deficient patients. The drug has a monoamine oxidase (MAO) inhibitory effect and should never be given concurrently to individuals already taking MAO inhibitors.
Protein Binding Not Available
Biotransformation Furazolidone is rapidly and extensively metabolized; the primary metabolic pathway identified begins with nitro-reduction to the aminofuran derivative. Two major metabolites are produced: 3-amino-2-oxazolidone (AOZ) or beta-hydroxyethylhydrazine (HEH). AOZ is responsible for monoamine oxidase inhibition. Detoxification and elimination of the drug is done primarily by conjugation with glutathione.
Half Life 10 minutes
Dosage Forms
Form Route
Liquid Oral
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Microbes (bacteria, parasites)
Phase 1 Metabolizing Enzymes
  1. Monoamine oxidase type B (MAO-B)
Targets
  1. DNA
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Monoamine oxidase type B (MAO-B)
Enzyme 1 Gene Name MAOB
Enzyme 1 SwissProt ID P27338 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P27338|AOFB_HUMAN Amine oxidase B 
SNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQKVKYVDLGGSYV
GPTQNRILRLAKELGLETYKVNEVERLIHHVKGKSYPFRGPFPPVWNPITYLDHNNFWRT
MDDMGREIPSDAPWKAPLAEEWDNMTMKELLDKLCWTESAKQLATLFVNLCVTAETHEVS
ALWFLWYVKQCGGTTRIISTTNGGQERKFVGGSGQVSERIMDLLGDRVKLERPVIYIDQT
RENVLVETLNHEMYEAKYVISAIPPTLGMKIHFNPPLPMMRNQMITRVPLGSVIKCIVYY
KEPFWRKKDYCGTMIIDGEEAPVAYTLDDTKPEGNYAAIMGFILAHKARKLARLTKEERL
KKLCELYAKVLGSLEALEPVHYEEKNWCEEQYSGGCYTTYFPPGILTQYGRVLRQPVDRI
YFAGTETATHWSGYMEGAVEAGERAAREILHAMGKIPEDEIWQSEPESVDVPAQPITTTF
LERHLPSVPGLLRLIGLTTIFSATALGFLAHKRGLLVRV
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.