Identification
- Summary
Nitrofural is a topical antibacterial for the prevention and treatment of bacterial infections of the skin.
- Generic Name
- Nitrofural
- DrugBank Accession Number
- DB00336
- Background
Nitrofural or nitrofurazone is a topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofural has also been administered orally in the treatment of trypanosomiasis.
Except for topical drug products formulated for dermatologic application, the FDA withdrew its approval for the use of drug products containing nitrofurazone.1
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved, Withdrawn
- Structure
Structure for Nitrofural (DB00336)
- Weight
- Average: 198.1362
Monoisotopic: 198.0389047 - Chemical Formula
- C6H6N4O4
- Synonyms
- 5-Nitro-2-furaldehyde semicarbazone
- Furacilin
- Nitrofural
- Nitrofurazone
Pharmacology
- Indication
For the treatment of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Skin infections •••••••••••• •••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Nitrofurazone is a topical antibacterial agent indicated as an adjunctive therapy for second and third degree burns when resistance to other agents is a real or potential problem. Nitrofurazone is also indicated in skin grafting when bacterial contamination may cause graft rejection or donor site infection, especially in hospitals with a history of resistant bacteria.
- Mechanism of action
The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.
Target Actions Organism AGlutathione reductase inhibitorEscherichia coli (strain K12) - Absorption
Well absorbed.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules (Polnaszek et al., 1984; Kutcher & McCalla, 1984; McCalla 1979; McCalla et al., 1975).
- Route of elimination
Not Available
- Half-life
5 hours
- Clearance
Not Available
- Adverse Effects
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Rat LD50 = 590 mg/kg; Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Furacin / Furaderm / Nitrofurazone
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ขี้ผึ้งแบ็คตาซิน Ointment 0.2 %w/w Topical บริษัท โอสถ อินเตอร์ แลบบอราทอรีส์ จำกัด จำกัด 1988-08-09 Not applicable Thailand 
ขี้ผึ้งโพลีซิน Ointment 0.2 %w/w Topical บริษัท แอดวานซ์ ฟาร์มาซูติคอล แมนูเฟคเจอริ่ง จำกัด 2014-02-06 Not applicable Thailand ฟูโซน ออยเมนท์ Ointment 0.2 %w/w Topical บริษัท เอเชี่ยนยูเนี่ยนแล็บบอราตอรี่ จำกัด จำกัด 1987-05-22 Not applicable Thailand เดนซ่า ครีม Cream 0.2 %w/w บริษัท สยามเภสัช จำกัด 2010-03-30 Not applicable Thailand ไมโตรซิน Ointment 0.2 %w/w Topical บริษัท โรงงานเภสัชกรรม เกร๊ทเตอร์ฟาร์ม่า จำกัด จำกัด 2013-10-30 2020-09-29 Thailand - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image FURADERM % 0,2 56 GR POMAD Nitrofural (0.2 %) Ointment Topical TOPRAK İLAÇ VE KİMYEVİ MADDELER SAN.VE TİC. A.Ş. 2013-01-29 Not applicable Turkey 
Categories
- ATC Codes
- B05CA03 — Nitrofural
- B05CA — Antiinfectives
- B05C — IRRIGATING SOLUTIONS
- B05 — BLOOD SUBSTITUTES AND PERFUSION SOLUTIONS
- B — BLOOD AND BLOOD FORMING ORGANS
- D08AF — Nitrofuran derivatives
- D08A — ANTISEPTICS AND DISINFECTANTS
- D08 — ANTISEPTICS AND DISINFECTANTS
- D — DERMATOLOGICALS
- D09AA — Medicated dressings with antiinfectives
- D09A — MEDICATED DRESSINGS
- D09 — MEDICATED DRESSINGS
- D — DERMATOLOGICALS
- Drug Categories
- Agents Against Leishmaniasis and Trypanosomiasis
- Anti-Infective Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Antiseptics and Disinfectants
- Blood and Blood Forming Organs
- Blood Substitutes and Perfusion Solutions
- Dermatologicals
- Furans
- Irrigating Solutions
- Medicated Dressings
- Medicated Dressings With Antiinfectives
- Nitro Compounds
- Nitrofuran Derivatives
- Nitrofurans
- Ophthalmologicals
- Otologicals
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- 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 / Semicarbazones / Heteroaromatic compounds / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Organic oxoazanium compounds / Organopnictogen compounds / Organic zwitterions / Organic oxides show 2 more
- Substituents
- 2-nitrofuran / Allyl-type 1,3-dipolar organic compound / Aromatic heteromonocyclic compound / C-nitro compound / Carbonic acid derivative / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / Nitroaromatic compound / Organic 1,3-dipolar compound show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Gram negative and gram positive bacteria
Chemical Identifiers
- UNII
- X8XI70B5Z6
- CAS number
- 59-87-0
- InChI Key
- IAIWVQXQOWNYOU-FPYGCLRLSA-N
- InChI
- InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+
- IUPAC Name
- [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
- SMILES
- NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O
References
- General References
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- External Links
- Human Metabolome Database
- HMDB0014480
- KEGG Drug
- D00862
- KEGG Compound
- C08042
- PubChem Compound
- 5447130
- PubChem Substance
- 46506509
- ChemSpider
- 4566720
- BindingDB
- 50420350
- 7455
- ChEMBL
- CHEMBL869
- ZINC
- ZINC000000897369
- PharmGKB
- PA164754877
- PDBe Ligand
- NFZ
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Nitrofurazone
- PDB Entries
- 1yki / 3r6w
- MSDS
- Download (73.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Recruiting Treatment Amyotrophic Lateral Sclerosis (ALS) 1 0 Terminated Treatment Osteomyelitis 1
Pharmacoeconomics
- Manufacturers
- Shire development inc
- Sherwood medical co
- Ambix laboratories div organics corp america
- Lannett co inc
- Perrigo new york inc
- Taro pharmaceuticals usa inc
- Wendt laboratories inc
- Packagers
- Gallipot
- Pharmedix
- Taro Pharmaceuticals USA
- Dosage Forms
Form Route Strength Insert Vaginal Ointment Topical Solution Topical 0.2 g Ointment Topical 0.2 % Ointment Topical 0.2 g Solution / drops Auricular (otic) 20 ml Solution Ophthalmic 0.02 % Suppository Vaginal Insert Vaginal 6 mg Ointment Topical 2 % Ointment Topical 200 mg Insert Vaginal 6.000 mg Ointment Topical 0.2 %w/w Liquid Auricular (otic) 2 mg/1g Cream 0.2 %w/w - Prices
Unit description Cost Unit Nitrofurazone powder 0.63USD 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) 238 dec °C PhysProp water solubility 210 mg/L (at 25 °C) BEILSTEIN logP 0.23 HANSCH,C ET AL. (1995) pKa 10 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.268 mg/mL ALOGPS logP 0.23 ALOGPS logP -0.14 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 11.79 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 123.76 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 44.21 m3·mol-1 Chemaxon Polarizability 16.97 Å3 Chemaxon Number of Rings 1 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 - 0.5716 Blood Brain Barrier + 0.9214 Caco-2 permeable - 0.5694 P-glycoprotein substrate Non-substrate 0.7552 P-glycoprotein inhibitor I Non-inhibitor 0.9271 P-glycoprotein inhibitor II Non-inhibitor 0.9278 Renal organic cation transporter Non-inhibitor 0.9347 CYP450 2C9 substrate Non-substrate 0.769 CYP450 2D6 substrate Non-substrate 0.8326 CYP450 3A4 substrate Non-substrate 0.6211 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9379 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8418 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9287 Ames test AMES toxic 0.9234 Carcinogenicity Non-carcinogens 0.692 Biodegradation Not ready biodegradable 0.7708 Rat acute toxicity 2.5276 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9188 hERG inhibition (predictor II) Non-inhibitor 0.9311
Spectra
- Mass Spec (NIST)
- Download (8.69 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00dl-6900000000-ab197de8a008fa662f84 Mass Spectrum (Electron Ionization) MS splash10-0pb9-9500000000-c26d5be0126e0a0e8278 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.7348122 predictedDarkChem Lite v0.1.0 [M-H]- 143.8774222 predictedDarkChem Lite v0.1.0 [M-H]- 145.0733122 predictedDarkChem Lite v0.1.0 [M-H]- 129.65858 predictedDeepCCS 1.0 (2019) [M+H]+ 144.6188122 predictedDarkChem Lite v0.1.0 [M+H]+ 148.9267434 predictedDarkChem Lite v0.1.0 [M+H]+ 144.6238122 predictedDarkChem Lite v0.1.0 [M+H]+ 132.91862 predictedDeepCCS 1.0 (2019) [M+Na]+ 144.3505122 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.3073122 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.2137122 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.05367 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nadp binding
- Specific Function
- Maintains high levels of reduced glutathione in the cytosol.
- Gene Name
- gor
- Uniprot ID
- P06715
- Uniprot Name
- Glutathione reductase
- Molecular Weight
- 48772.195 Da
References
- Vega-Teijido M, Caracelli I, Zukerman-Schpector J: Conformational analyses and docking studies of a series of 5-nitrofuran- and 5-nitrothiophen-semicarbazone derivatives in three possible binding sites of trypanothione and glutathione reductases. J Mol Graph Model. 2006 Mar;24(5):349-55. Epub 2005 Nov 7. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xanthine oxidase activity
- Specific Function
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- Tatsumi K, Kitamura S, Yoshimura H: Reduction of nitrofuran derivatives by xanthine oxidase and microsomes. Isolation and identification of reduction products. Arch Biochem Biophys. 1976 Jul;175(1):131-7. [Article]
- Kutcher WW, McCalla DR: Aerobic reduction of 5-nitro-2-furaldehyde semicarbazone by rat liver xanthine dehydrogenase. Biochem Pharmacol. 1984 Mar 1;33(5):799-805. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:40