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Identification
NameFurazolidone
Accession NumberDB00614  (APRD00988)
Typesmall molecule
Groupsapproved
Description

A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone binds bacterial DNA which leads to the gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)

Structure
Thumb
Synonyms
SynonymLanguageCode
5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimineNot AvailableNot Available
FZLNot AvailableNot Available
NitrofurazolidoneNot AvailableNot Available
NitrofurazolidonumNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Dependal-MGlaxoSmithKline
FuroxoneRoberts Laboratories
Brand mixturesNot Available
Categories
CAS number67-45-8
WeightAverage: 225.1583
Monoisotopic: 225.038570349
Chemical FormulaC8H7N3O5
InChI KeyInChIKey=PLHJDBGFXBMTGZ-WEVVVXLNSA-N
InChI
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+
IUPAC Name
3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one
SMILES
[O-][N+](=O)C1=CC=C(O1)C=NN1CCOC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassFurans
SubclassNitrofurans
Direct parentNitrofurans
Alternative parentsOxazolidinediones; Hydrazones; Aldimines; Nitro Compounds; Nitronic Acids; Organic Oxoazanium Compounds; Polyamines
Substituentsoxazolidinedione; hydrazone; nitro compound; nitronic acid; aldimine; polyamine; organic oxoazanium; imine; organonitrogen compound; amine
Classification descriptionThis compound belongs to the nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Pharmacology
IndicationFor the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.
PharmacodynamicsFuroxone 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 actionFurazolidone 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.
AbsorptionRadiolabeled drug studies indicate that furazolidone is well absorbed following oral administration
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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.

SubstrateEnzymesProduct
Furazolidone
    beta-HydroxyethylhydrazineDetails
    Furazolidone
      3-amino-2-oxazolidoneDetails
      Route of eliminationNot Available
      Half life10 minutes
      ClearanceNot Available
      ToxicityReactions 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.
      Affected organisms
      • Microbes (bacteria, parasites)
      PathwaysNot Available
      SNP Mediated EffectsNot Available
      SNP Mediated Adverse Drug ReactionsNot Available
      ADMET
      Predicted ADMET features
      Property Value Probability
      Human Intestinal Absorption + 0.9038
      Blood Brain Barrier + 0.9117
      Caco-2 permeable - 0.5736
      P-glycoprotein substrate Non-substrate 0.7829
      P-glycoprotein inhibitor I Non-inhibitor 0.7761
      P-glycoprotein inhibitor II Non-inhibitor 0.9597
      Renal organic cation transporter Non-inhibitor 0.8351
      CYP450 2C9 substrate Non-substrate 0.8117
      CYP450 2D6 substrate Non-substrate 0.8415
      CYP450 3A4 substrate Substrate 0.5984
      CYP450 1A2 substrate Inhibitor 0.9107
      CYP450 2C9 substrate Non-inhibitor 0.907
      CYP450 2D6 substrate Non-inhibitor 0.9134
      CYP450 2C19 substrate Non-inhibitor 0.9026
      CYP450 3A4 substrate Non-inhibitor 0.928
      CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8828
      Ames test AMES toxic 0.9108
      Carcinogenicity Non-carcinogens 0.9097
      Biodegradation Ready biodegradable 0.8978
      Rat acute toxicity 2.1639 LD50, mol/kg Not applicable
      hERG inhibition (predictor I) Weak inhibitor 0.7889
      hERG inhibition (predictor II) Non-inhibitor 0.9057
      Pharmacoeconomics
      Manufacturers
      • Shire development inc
      Packagers
      • Professional Co.
      Dosage forms
      FormRouteStrength
      LiquidOral
      TabletOral
      Prices
      Unit descriptionCostUnit
      Furazolidone powder2.04USDg
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      PatentsNot Available
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      melting point255 °CPhysProp
      water solubility40 mg/L (at 25 °C)MERCK INDEX (1996); pH 6
      logP-0.04DEBNATH,AK ET AL. (1991)
      Predicted Properties
      PropertyValueSource
      water solubility3.64e-01 g/lALOGPS
      logP0.15ALOGPS
      logP0.87ChemAxon
      logS-2.8ALOGPS
      pKa (strongest basic)-2.4ChemAxon
      physiological charge0ChemAxon
      hydrogen acceptor count4ChemAxon
      hydrogen donor count0ChemAxon
      polar surface area100.86ChemAxon
      rotatable bond count3ChemAxon
      refractivity51.09ChemAxon
      polarizability19.74ChemAxon
      number of rings2ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterYesChemAxon
      Veber's ruleNoChemAxon
      MDDR-like ruleNoChemAxon
      Spectra
      SpectraNot Available
      References
      Synthesis Reference

      DrugSyn.org

      US2742462
      General ReferenceNot Available
      External Links
      ResourceLink
      KEGG DrugD00830
      KEGG CompoundC07999
      PubChem Compound5323714
      PubChem Substance46507291
      ChemSpider3317
      ChEBI5195
      ChEMBLCHEMBL1103
      Therapeutic Targets DatabaseDAP000993
      PharmGKBPA164746760
      Drug Product Database674761
      RxListhttp://www.rxlist.com/cgi/generic2/furazol.htm
      Drugs.comhttp://www.drugs.com/cons/furazolidone.html
      WikipediaFurazolidone
      ATC CodesG01AX06
      AHFS CodesNot Available
      PDB EntriesNot Available
      FDA labelNot Available
      MSDSshow(74.1 KB)
      Interactions
      Drug Interactions
      Drug
      MilnacipranIncrease serotonin levels. Combination therapy is contraindicated.
      TetrabenazineTetrabenazine may increase the adverse/toxic effects of Furazolidine. Concomitant therapy is contraindicated.
      TolcaponeTolcapone and Furazolidone decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
      TramadolTramadol increases the risk of serotonin syndrome and seizure induction by the MAO inhibitor, Furazolidone.
      TranylcypromineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
      TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
      TrimipramineIncreased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
      VenlafaxineIncreased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
      ZolmitriptanThe MAO inhibitor, furazolidine, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing furazolidine are contraindicated.
      Food InteractionsNot Available

      1. DNA

      Kind: nucleotide

      Organism: Human

      Pharmacological action: yes

      Actions: cross-linking/alkylation

      Components

      Name UniProt ID Details

      References:

      1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. 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
      3. Meng J, Mangat SS, Grudzinski IP, Law FC: Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout. Drug Metabol Drug Interact. 1998;14(4):209-19. Pubmed

      1. Amine oxidase [flavin-containing] B

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Amine oxidase [flavin-containing] B P27338 Details

      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
      2. Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. Pubmed
      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

      2. Amine oxidase [flavin-containing] A

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Amine oxidase [flavin-containing] A P21397 Details

      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
      2. Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. Pubmed
      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

      Comments
      Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:23