{[(5-nitrofuran-2-yl)methylidene]amino}urea

• ChemBase ID: 220
• Molecular Formular: C6H6N4O4
• Molecular Mass: 198.13624
• Monoisotopic Mass: 198.03890469
• SMILES: o1c(ccc1[N+](=O)[O-])/C=N/NC(=O)N
• Canonical SMILES: NC(=O)N/N=C/c1ccc(o1)[N+](=O)[O-]
• 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+
• InChIKey: IAIWVQXQOWNYOU-FPYGCLRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(5-nitrofuran-2-yl)methylidene]amino}urea; [(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
• IUPAC Traditional name: 5-nitrofurfural semicarbazone; nitrofurazone
• Brand Name: Actin-N; Aldomycin; Alfucin; Amifur; Babrocid; Becafurazone; Biofuracina; Biofurea; Chemofuran; Chixin; Cocafurin; Coxistat; Dermofural; Dymazone; Dynazone; Eldezol; Eldezol F-6; Fedacin; Flavazone; Fracine; Furacilin; Furacillin; Furacin; Furacin Soluble Dressing; Furacin Topical Cream; Furacin Topical Solution; Furacin-E; Furacin-HC; Furacine; Furacinetten; Furacoccid; Furacort; Furacycline; Furaderm; Furagent; Furalcyn; Furaldon; Furalone; Furametral; Furan-Ofteno; Furaplast; Furaseptyl; Furaskin; Furatsilin; Furaziline; Furazin; Furazina; Furazol W; Furazone; Furazyme; Furesol; Furfurin; Furosem; Fuvacillin; Hemofuran; Ibiofural; Mammex; Mastofuran; Monafuracin; Monafuracis; Monofuracin; NF-7; NFS; Nefco; Nifucin; Nifurid; Nifuzon; Nitrofural; Nitrofuran; Nitrofurane; Nitrofurol; Nitrozone; Otofural; Otofuran; Sanfuran; Spray-Dermis; Spray-Foral; Vabrocid; Vadrocid; Yatrocin
• Synonyms: Nitrofurazone solution; 5-Nitro-2-furaldehyde semicarbazone; 5-Nitro-2-furfural semicarbazone; Furacin; 2-[(5-Nitro-2-furanyl)methylene]hydrazinecarboxamide; (5-Nitro-2-furfurylidenamino)urea; 1-(5-Nitro-2-furfurylidene)semicarbazide; Aldomycin; Alfucin; Amifur; Babrocid; Chemofuran; Coxistat; Furesol; Mammex; Mastofuran; Nitrozone; Otofural; Vabrocid; Nitrofural; Nitrofurazone; 5-NITRO-2-FURALDEHYDE SEMICARBAZONE; 5-NITROFURFURALSEMICARBAZONE; NF; NFZ; Nitrofurazan; Nitrofurazone; Nitrofural; Furacilin; ACTIN-N; Otofuran; 5-硝基-2-亚糠基半卡巴腙; 呋喃西林 溶液; 5-硝基-2-呋喃甲醛半卡腙; 呋喃西林; 硝呋醛; 5-硝基-2-糠醛半卡巴腙

Database IDs

• CAS Number: 59-87-0
• EC Number: 200-443-1; 200-835-2
• MDL Number: MFCD00003225
• Beilstein Number: 86403; 1347298
• Merck Index: 146600
• PubChem SID: 24886543; 160963683; 46506509; 24869937
• PubChem CID: 5447130
• ATC CODE: D08AF01; QG01AX90; QP51AC02; D09AA03; S01AX04; S02AA02; P01CC02; B05CA03
• CHEMBL: 869
• Chemspider ID: 4566720
• DrugBank ID: DB00336
• KEGG ID: C08042
• Unique Ingredient Identifier: X8XI70B5Z6
• Wikipedia Title: Nitrofural

CALCULATED PROPERTIES

JChem

• LogD (pH = 5.5): -0.13506359
• LogD (pH = 7.4): -0.13507833
• Log P: -0.13506338
• Molar Refractivity: 44.2064 cm^3
• Polarizability: 16.137276 Å^3
• Polar Surface Area: 123.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 11.794831
• H Acceptors: 4
• H Donor: 2

ALOGPS 2.1

• Log P: 0.23
• LOG S: -2.87
• Solubility (Water): 2.68e-01 g/l

PROPERTIES

Physical Property

• Solubility: 210 mg/L (Approximately 50%); DMSO
• Apperance: Yellow Solid
• Melting Point: 235-237°C; 242-244 °C(lit.); 242-244°C; ca 240°C dec.
• Flash Point: 2 °C; 35.6 °F
• Hydrophobicity(logP): 0.2

Safety Information

• Storage Condition: -20°C; 2-8°C, Protect from light; Refrigerator
• Storage Warning: Light Sensitive
• RTECS: LT7700000
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 1648
• German water hazard class: 2; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 22; 22-40-62-68; R:22
• Safety Statements: 16-36/37; 36; 36/37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H302-H312-H319-H332; H301-H341-H351-H361; H302-H317
• GHS Precautionary statements: P210-P280-P305 + P351 + P338; P280; P281-P301+P310-P321-P308+P313-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1648 3/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Pregnancy Category: C (US)

Product Information

• Purity: ≥97.0% (HPLC); 97%; 98+%
• Concentration: 100 ng/μL in acetonitrile
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C6H6N4O4

DETAILS

MP Biomedicals - 02155880

(Nitrofurazone)

MP Biomedicals - 05216984

MP Biomedicals Rare Chemical collection

DrugBank - DB00336

• Drug Groups: approved
• Description: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis. [PubChem]
• Indication: For the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.
• Pharmacology: 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.
• Toxicity: Rat LD₅₀ = 590 mg/kg; Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated.
• Affected Organisms: Gram negative and gram positive bacteria
• Biotransformation: 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).
• Absorption: Well absorbed.
• Half Life: 5 hours
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1644

Research Area: Infection
Biological Activity:
Nitrofurazone is a topical anti-infective agent with an IC50 of 22.83 ± 1.2 µM, and effective against gram-negative and gram-positive bacteria. (Rat LD50 = 590 mg/kg)[1] Nitrofurazone (NF) and its derivative, hydroxymethylnitrofurazone (NFOH), have presented antichagasic activity. In vitro cruzain inhibition tests were performed for both compounds, and the 50% inhibitory concentration (IC50) for NF and NFOH presented values of 22.83 ± 1.2 µM and 10.55 ± 0.81 µM, respectively. AM1 semi-empirical molecular modeling studies were performed to understand the activity of the compounds, corroborating the observed cruzain inhibitory activity. [2]

Sigma Aldrich - 73340

Packaging
100, 500 g in poly bottle

Sigma Aldrich - 31706

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - N493880

Anti-infective (topical). Antimicrobial.

REFERENCES

• http://en.wikipedia.org/wiki/Nitrofurazone
• Morris, et al.: Cancer Res., 29, 2145 (1969)
• Sanderson, H., et al.: Toxicol. Lett., 144, 383 (1969)