Nitrofurazone

CAS# 59-87-0

Nitrofurazone

2D Structure

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Nitrofurazone

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Chemical Properties of Nitrofurazone

Cas No. 59-87-0 SDF Download SDF
PubChem ID 5447130 Appearance Powder
Formula C6H6N4O4 M.Wt 198.14
Type of Compound N/A Storage Desiccate at -20°C
Synonyms NFZ; Nitrofural
Solubility DMSO : ≥ 155 mg/mL (782.28 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name [(E)-(5-nitrofuran-2-yl)methylideneamino]urea
SMILES C1=C(OC(=C1)[N+](=O)[O-])C=NNC(=O)N
Standard InChIKey IAIWVQXQOWNYOU-FPYGCLRLSA-N
Standard 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+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Nitrofurazone

DescriptionNitrofural is a bactericidal compound used as an antibiotic most commonly in the form of ointments. Target: Antibacterial Nitrofurazone, a nitroaromatic drug, is a broad spectrum antibiotic which has until now been considered as activated in bacteria by nitroreductases. Its use in medicine has become less frequent as safer and more effective products have become available, and it has been discontinued in the US. 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.

References:
[1]. Ryan A, et al. Activation of nitrofurazone by azoreductases: multiple activities in one enzyme. Sci Rep. 2011;1:63.

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Background on Nitrofurazone

Anti-infective (topical) and antimicrobial.

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References on Nitrofurazone

Comparison of the Effect of Aloe Vera Gel and Nitrofurazone 2% on Epithelialization and Granulation Tissue Formation Regarding Superficial Second-Degree Burns.[Pubmed:27840469]

Iran J Med Sci. 2016 May;41(3 Suppl):S3.

BACKGROUND: Therapeutic effects of various treatment options in burn wound healing have been one of the most controversial issues in wound care. Aloe Vera is an herbal medicine, which has wound healing effects on chronic wound. The present study was carried out to examine and compare the effect of Aloe Vera gel and Nitrofurazone 2% on epithelialization and granulation tissue formation with respect to superficial second-degree burns. METHODS: This is a randomized clinical trial and the sampling method was used based on pre-defined inclusion criteria. The sample size was 30 patients that were admitted to Kerman burn center, including patients that had superficial burn in the symmetry limb, who were chosen based on depth burn and the qualifications needed for the study. One part of the burned area was dressed using ointment Nitrofurazone 2% (according to routine care in the hospital) and the symmetry part was dressed using Aloe Vera gel. The tools for data collection included a demographic questionnaire, tools of bats-joints for checking epithelialization and granulation tissue. The burn wound epithelialization and granulation at the beginning of patient's admission and the first, second and third weeks after dressing were assessed and recorded. RESULTS: In patients treated with Aloe Vera gel, epithelialization and granulation tissue of burn wounds were remarkably earlier than those patients treated with Nitrofurazone 2% (P<0.05). CONCLUSION: In conclusion, Aloe Vera gel enhanced epithelialization and granulation tissue of burn wounds in superficial second-degree burn patients better than Nitrofurazone 2%. The mechanism of the remarkable efficacy of Aloe Vera gel in the epithelialization and granulation tissue of burn injuries may be explained by its hydrocolloid and moisturizing and anti-inflammatory effects.

Identification and quantification of nitrofurazone metabolites by ultraperformance liquid chromatography-quadrupole time-of-flight high-resolution mass spectrometry with precolumn derivatization.[Pubmed:28124755]

Anal Bioanal Chem. 2017 Mar;409(9):2255-2260.

An ultraperformance liquid chromatography-quadrupole time-of-flight high-resolution mass spectrometry method was developed and validated for the determination of Nitrofurazone metabolites. Precolumn derivatization with 2,4-dinitrophenylhydrazine and p-dimethylaminobenzaldehyde as an internal standard was used successfully to determine the biomarker 5-nitro-2-furaldehyde. In negative electrospray ionization mode, the precise molecular weights of the derivatives were 320.0372 for the biomarker and 328.1060 for the internal standard (relative error 1.08 ppm). The matrix effect was evaluated and the analytical characteristics of the method and derivatization reaction conditions were validated. For comparison purposes, spiked samples were tested by both internal and external standard methods. The results show high precision can be obtained with p-dimethylaminobenzaldehyde as an internal standard for the identification and quantification of Nitrofurazone metabolites in complex biological samples. Graphical Abstract A simplified preparation strategy for biological samples.

Foot contact dermatitis: nitrofurazone as the main cause in a retrospective, cross-sectional study over a 16-year period from Turkey.[Pubmed:27496199]

Int J Dermatol. 2016 Dec;55(12):1345-1350.

BACKGROUND: The major causative agents in allergic contact dermatitis of the foot may differ from country to country. Sufficient data on foot eczema in patients from Turkey are lacking. OBJECTIVE: To identify the clinically relevant contact allergens in foot eczema and determine the role of patch test series and patients' own materials in the detection of the responsible allergens. METHODS: Among 1753 patients patch tested between 1996 and 2012 in our clinic, 53 with suspected allergic foot eczema were enrolled in this retrospective, cross-sectional study. Forty nine patients were patch tested with the extended European baseline series, 49 with supplemental series including rubber, leather, topical drugs, textile, cosmetic series containing preservatives and emulgators and varnish/plastic/glue series, and 37 with their own substances. RESULTS: Thirty of the 53 patch tested patients showing sensitization to at least one clinically relevant allergen were diagnosed with allergic foot eczema. The main eliciting agent was Nitrofurazone (n = 8), followed by leather shoe allergens, ie, potassium dichromate (n = 6), p-tert-butylphenol formaldehyde resin and formaldehyde, in the second range. Rubber shoe allergens were less frequently observed (n = 3). In more than 1/3 of the patients, the causative agent could only be identified by testing the patient's own substances and/or supplemental series. CONCLUSION: Nitrofurazone was the leading causative agent followed by leather shoe allergens. Pediatric patients were frequently sensitized with shoe allergens. Patch testing with patient's own substances had a critical value in the detection of the causative agent in a significant number of patients.

Description

Nitrofurazone (NFZ;Nitrofural) is a bactericidal compound used as an antibiotic most commonly in the form of ointments.

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