Identification

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Name
Furazolidone
Accession Number
DB00614  (APRD00988)
Type
Small Molecule
Groups
Experimental, Vet approved
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
  • 3-(5'-Nitrofurfuralamino)-2-oxazolidone
  • 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone
  • 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidone
  • 3-[(5-Nitrofurylidene)amino]-2-oxazolidone
  • 3-{[(5-nitro-2-furanyl)methylene]amino}-2-oxazolidinone
  • 5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimine
  • Furazolidona
  • Furazolidonum
  • FZL
  • N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone
  • N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-one
  • Nitrofurazolidone
  • Nitrofurazolidonum
External IDs
USAF EA-1
International/Other Brands
Dependal-M (GlaxoSmithKline) / Furoxone (Roberts Laboratories)
Categories
UNII
5J9CPU3RE0
CAS number
67-45-8
Weight
Average: 225.1583
Monoisotopic: 225.038570349
Chemical Formula
C8H7N3O5
InChI Key
PLHJDBGFXBMTGZ-UHFFFAOYSA-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
IUPAC Name
3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one
SMILES
[H]C(=NN1CCOC1=O)C1=CC=C(O1)[N+]([O-])=O

Pharmacology

Indication

For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.

Pharmacodynamics

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.

TargetActionsOrganism
ADNA
cross-linking/alkylation
Humans
Absorption

Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration

Volume of distribution
Not Available
Protein binding
Not 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.

Route of elimination
Not Available
Half life

10 minutes

Clearance
Not Available
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.

Affected organisms
  • Microbes (bacteria, parasites)
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Furazolidone is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Furazolidone is combined with 1-benzylimidazole.
2,4-thiazolidinedioneFurazolidone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineFurazolidone may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineFurazolidone may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineFurazolidone may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineFurazolidone may increase the hypertensive activities of 4-Methoxyamphetamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0014752
KEGG Drug
D00830
KEGG Compound
C07999
PubChem Compound
3435
PubChem Substance
46507291
ChemSpider
3317
ChEBI
5195
ChEMBL
CHEMBL1374738
Therapeutic Targets Database
DAP000993
PharmGKB
PA164746760
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Furazolidone
ATC Codes
G01AX06 — Furazolidone
MSDS
Download (74.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Ulcer / Gastritis / Gastritis Chronic / Malignant Neoplasm of Stomach1
4CompletedTreatmentFunctional Dyspepsia / Scarred Peptic Ulcer1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Triple Therapy1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)5
4RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentDuodenal Ulcer Due to Helicobacter Pylori1
4RecruitingTreatmentHelicobacter Pylori1
Not AvailableCompletedTreatmentTreatment of Helicobacter Pylori1

Pharmacoeconomics

Manufacturers
  • Shire development inc
Packagers
  • Professional Co.
Dosage forms
Not Available
Prices
Unit descriptionCostUnit
Furazolidone powder2.04USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)254-256Drake, 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 Solubility0.364 mg/mLALOGPS
logP0.15ALOGPS
logP0.87ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area98.18 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.08 m3·mol-1ChemAxon
Polarizability19.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9038
Blood Brain Barrier+0.9117
Caco-2 permeable-0.5736
P-glycoprotein substrateNon-substrate0.7829
P-glycoprotein inhibitor INon-inhibitor0.7761
P-glycoprotein inhibitor IINon-inhibitor0.9597
Renal organic cation transporterNon-inhibitor0.8351
CYP450 2C9 substrateNon-substrate0.8117
CYP450 2D6 substrateNon-substrate0.8415
CYP450 3A4 substrateSubstrate0.5984
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9134
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.928
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8828
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.9097
BiodegradationReady biodegradable0.8978
Rat acute toxicity2.1639 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7889
hERG inhibition (predictor II)Non-inhibitor0.9057
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Furans
Sub Class
Nitrofurans
Direct Parent
Nitrofurans
Alternative Parents
Nitroaromatic compounds / Oxazolidinones / Heteroaromatic compounds / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Organic oxoazanium compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
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
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
oxazolidines, nitrofuran antibiotic (CHEBI:5195)

Targets

Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Cross-linking/alkylation
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.
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:17139284]
  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:17016423]
  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:10694929]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase 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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin binding
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
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]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 05:29