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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyFurazolidone
Identification
- 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
Structure for Furazolidone (DB00614)
- 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
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Anti-Infective Agents, Urinary
- Antiparasitic Agents
- Antiprotozoals
- Antitrichomonal Agents
- Central Nervous System Depressants
- Enzyme Inhibitors
- Furans
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Monoamine Oxidase Inhibitors
- Nitro Compounds
- Nitrofurans
- Oxazoles
- Oxazolidinones
- Renal Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- 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.
Target Actions Organism ADNA cross-linking/alkylationHuman - 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
Drug Interaction (R)-warfarin The risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with (S)-Warfarin. 2,4-thiazolidinedione Furazolidone may increase the hypoglycemic activities of 2,4-thiazolidinedione. 2,5-Dimethoxy-4-ethylamphetamine Furazolidone may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine Furazolidone may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylthioamphetamine. 3,4-Methylenedioxyamphetamine Furazolidone may increase the hypertensive activities of 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine Furazolidone may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine. 4-hydroxycoumarin The risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with 4-hydroxycoumarin. 4-Methoxyamphetamine Furazolidone may increase the hypertensive activities of 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Furazolidone. - 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
Phase Status Purpose Conditions Count 4 Completed Treatment Functional Dyspepsia / Scarred Peptic Ulcer 1 4 Not Yet Recruiting Treatment Antimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori) 1 4 Not Yet Recruiting Treatment Antimicrobial Susceptibility Testing / Triple Therapy 1 4 Not Yet Recruiting Treatment Bacterial Infection Due to Helicobacter Pylori (H. Pylori) 2 4 Not Yet Recruiting Treatment Bacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Ulcer (GU) / Gastritis / Gastritis Chronic / Malignant Neoplasm of Stomach 1 4 Recruiting Treatment Antimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori) 1 4 Recruiting Treatment Bacterial Infection Due to Helicobacter Pylori (H. Pylori) 1 4 Recruiting Treatment Duodenal Ulcer Due to Helicobacter Pylori 1 Not Available Completed Treatment Treatment of Helicobacter Pylori 1
Pharmacoeconomics
- Manufacturers
- Shire development inc
- Packagers
- Professional Co.
- Dosage forms
- Not Available
- Prices
Unit description Cost Unit Furazolidone powder 2.04USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 254-256 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 water solubility 40 mg/L (at 25 °C) MERCK INDEX (1996); pH 6 logP -0.04 DEBNATH,AK ET AL. (1991) - Predicted Properties
Property Value Source Water Solubility 0.364 mg/mL ALOGPS logP 0.15 ALOGPS logP 0.87 ChemAxon logS -2.8 ALOGPS pKa (Strongest Basic) -2.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 100.86 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 51.09 m3·mol-1 ChemAxon Polarizability 19.74 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9134 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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
1. DNA
Yes
Cross-linking/alkylation
- General Function:
- Used for biological information storage.
- Specific Function:
- DNA contains the instructions needed for an organism to develop, survive and reproduce.
- Molecular Weight:
- 2.15 x 1012 Da
References
- 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]
- 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]
- 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
- Human
- 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
- 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]
- Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. [PubMed:10543364]
- 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
- Human
- 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
- 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]
- Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. [PubMed:10543364]
- 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 October 01, 2018 12:51