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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
3-(5'-Nitrofurfuralamino)-2-oxazolidoneNot AvailableNot Available
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinoneNot AvailableNot Available
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidoneNot AvailableNot Available
3-[(5-Nitrofurylidene)amino]-2-oxazolidoneNot AvailableNot Available
3-{[(5-nitro-2-furanyl)methylene]amino}-2-oxazolidinoneNot AvailableNot Available
5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimineNot AvailableNot Available
FurazolidonaNot AvailableNot Available
FurazolidoneNot AvailableNot Available
FurazolidonumNot AvailableNot Available
FuroxoneNot AvailableNot Available
FZLNot AvailableNot Available
N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidoneNot AvailableNot Available
N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-oneNot 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 KeyPLHJDBGFXBMTGZ-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
Not Available
beta-HydroxyethylhydrazineDetails
Furazolidone
Not Available
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 point254-256Drake, G.D., Gever, G. and Hayes, K.J.; U.S. Patent 2,759,931; August 21, 1956; assigned to The Norwich Pharmacal Company. Gever, G. and O'Keefe, C.J.; U.S. Patent 2,927,l IO; March 1, 1960; assigned to The Norwich Pharmacal Company
water solubility40 mg/L (at 25 °C)MERCK INDEX (1996); pH 6
logP-0.04DEBNATH,AK ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility0.364ALOGPS
logP0.15ALOGPS
logP0.87ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area100.86 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.09 m3·mol-1ChemAxon
Polarizability19.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Drake, G.D., Gever, G. and Hayes, K.J.; U.S. Patent 2,759,931; August 21, 1956; assigned to The Norwich Pharmacal Company.
Gever, G. and O’Keefe, C.J.; U.S. Patent 2,927,l IO; March 1, 1960; assigned to The Norwich Pharmacal Company.

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

Targets

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

Enzymes

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

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Drug created on June 13, 2005 07:24 / Updated on April 24, 2014 13:53