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Nitrofurazone

CAS No.
59-87-0
Chemical Name:
Nitrofurazone
Synonyms
NFS;NF;semicarbazone;NITROFURAL;FURACILIN;5-NITRO-2-FURALDEHYDE SEMICARBAZONE;Actin-N;FURACIN;Furazone;Furfurin
CBNumber:
CB0492724
Molecular Formula:
C6H6N4O4
Molecular Weight:
198.14
MDL Number:
MFCD00003225
MOL File:
59-87-0.mol
MSDS File:
SDS
Last updated:2024-03-12 17:20:04

Nitrofurazone Properties

Melting point 242-244 °C (lit.)
Boiling point 335.43°C (rough estimate)
Density 1.6031 (rough estimate)
refractive index 1.6500 (estimate)
Flash point 2 °C
storage temp. 2-8°C
solubility Very slightly soluble in water, slightly soluble in ethanol (96 per cent).
pka pKa 9.28± 0.03( EtOH,t =35±0.1,I=0.00) (Uncertain)
color Yellow to Dark Yellow
Water Solubility <0.1 g/100 mL at 19 ºC
Sensitive Light Sensitive
Merck 14,6600
BRN 86403
InChIKey IAIWVQXQOWNYOU-FPYGCLRLSA-N
CAS DataBase Reference 59-87-0(CAS DataBase Reference)
FDA 21 CFR 530.41
EWG's Food Scores 1
FDA UNII X8XI70B5Z6
Proposition 65 List Nitrofurazone
ATC code B05CA03,D08AF01,D09AA03,P01CC02,S01AX04,S02AA02
IARC 3 (Vol. 50) 1990
NIST Chemistry Reference 5-Nitro furfural semicarbazone(59-87-0)
EPA Substance Registry System Nitrofurazone (59-87-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H317-H341-H351-H361fd-H373-H412
Precautionary statements  P202-P273-P280-P301+P312-P302+P352-P308+P313
Hazard Codes  Xn,F
Risk Statements  22-36-20/21/22-11
Safety Statements  36-36/37-26-16
RIDADR  3249
WGK Germany  3
RTECS  LT7700000
8
TSCA  Yes
HazardClass  6.1(b)
PackingGroup  III
HS Code  29321900
Toxicity LD50 in rats (g/kg): 0.59 orally; 3.0 s.c. (Godwin)
NFPA 704
1
2 0

Nitrofurazone price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0002295 Nitrofural for peak identification A European Pharmacopoeia (EP) Reference Standard 59-87-0 Y0002295 $161 2024-03-01 Buy
Sigma-Aldrich 1465004 Nitrofurazone United States Pharmacopeia (USP) Reference Standard 59-87-0 200mg $436 2024-03-01 Buy
TCI Chemical N0200 Nitrofurazone >98.0%(HPLC)(E) 59-87-0 25g $19 2024-03-01 Buy
TCI Chemical N0200 Nitrofurazone >98.0%(HPLC)(E) 59-87-0 250g $91 2024-03-01 Buy
Alfa Aesar A18593 5-Nitro-2-furaldehyde semicarbazone, 98+% 59-87-0 25g $27.65 2024-03-01 Buy
Product number Packaging Price Buy
Y0002295 Y0002295 $161 Buy
1465004 200mg $436 Buy
N0200 25g $19 Buy
N0200 250g $91 Buy
A18593 25g $27.65 Buy

Nitrofurazone Chemical Properties,Uses,Production

Description

Nitrofurazone is an antibacterial agent used in animal feed. Occupational dermatitis was reported in cattle breeders and farmers.

Chemical Properties

white to light yellow crystal powde

Originator

Furacin,Norwich Eaton ,US,1946

Uses

Nitrofurazone is a topical anti-infective and bactericide for most pathogens commonly causing surface infections; in the adjunctive therapy of patients with second and third degree bums when bacterial resistance to other agents is areal or potential problem; in skin grafting where bacterial contamination may cause graft rejection and/or donor-site infection; antibacterial agent for the treatment or prevention of infections in a variety of conditions involving skin, eyes, ears, nose and genito-urinary tract; used on pyodermas, ulcers, and wounds; affects some protozoa and is an effective prophylaxis against nosocomial infections; antiseptic lubricant for trans urethral resection; anti-microbial in veterinary medicine.

Uses

Anti-infective (topical). Antimicrobial.Environmental contaminants; Food contaminants; Heat processing contaminants

Definition

A type of organic compound containing the C:N.NH.CO.NH2 grouping, formed by reaction of an aldehyde or ketone with semicarbazide (H2N.NH.CO.NH2). The compounds are crystalline solids with sharp melting points, which can be used to characterize the original aldehyde or ketone.

Indications

Nitrofurazone (Furacin), a synthetic nitrofuran derivative with a broad antibacterial spectrum. Although its exact mechanism of action is unknown, it is thought to inhibit bacterial enzymes involved in carbohydrate metabolism. It is not effective against fungal or viral organisms. It is used as adjunctive therapy in patients with second- and third-degree burns when bacterial resistance to other antiinfective agents is a potential problem. It is not effective in the treatment ofminor burns or superficial bacterial infections involving wounds, cutaneous ulcers, or various pyodermas. It is rarely used by dermatologists as it carries a high risk of acquired contact sensitivity.

Definition

ChEBI: A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcer , wounds and skin infections.

Manufacturing Process

A mixture of 43 grams of semicarbazide hydrochloride and 31 grams of sodium acetate is dissolved in 150 cc of water. The pH of this solution is approximately 5. Ethyl alcohol (95% by volume) in the amount of 250 cc is added and the mixture is stirred mechanically. A solution of 53.5 grams of carefully purified 2-formyl-5-nitrofuran in 250 cc of the said alcohol is added dropwise to the semicarbazide solution at room temperature. After completing the addition of the aldehyde solution, the mixture is stirred for another hour. The precipitate is removed from the reaction mixture by filtration. It is washed well with ethyl alcohol and dried to constant weight at 70°C in an oven. The product weighs 73 grams, corresponding to a yield of 97%. It is obtained in the form of pale yellow needles, which are not subjected to further purification, according to US Patent 2,416,234.

brand name

Actin-N (Sherwood); Furacin (Shire);Acmor-s;Akutol;Anginofur;Auroid;Beca furazona;Bifuran;Burnazone;Dermobion;Ectofural;Escofuran;Escofuron;Fluorobioptal;Furacilinum;Furacinas;Furacinethin;Furacin-sol;Furacin-streusol;Furacocid;Furacol;Furaseptin;Fura-septin;Fura-vet;Furea;Furesan;Furotalgin;Furovol;Germax;Germex;Ginejuvent;I fomula;Ii formula;Kamfomen;Kindrog;Lifuzol;Mammiject;Mastidol;Muldacin;Neovagon;Nfz 1;Nitocetin;Nitrocol plus;Nitro-rea;Notaba;Sanifur;Scandantin;Sulfamyton-n;Taristop;Tranoxa;Tuocurine;Urafadyn;Uroletten;Viropulver;Yalrocin;Zoppin spray blu.

Therapeutic Function

Topical antiinfective

World Health Organization (WHO)

Nitrofural, a nitrofuran derivative with broad-spectrum antibacterial activity, was introduced in the early 1940s for the topical treatment of various skin conditions. It has also been used systemically for the treatment of African trypasonomiasis. Following recent findings of in vitro mutagenicity and of carcinogenicity in experimental animals, use of topical preparations containing this substance was restricted in Germany. Nitrofural remains registered in several countries and the World Health Organization is not aware of restrictive action having been taken elsewhere.

General Description

Odorless pale yellow needles or yellow powder. pH (saturated aqueous solution) 6.0 - 6.5. Alkaline solutions are dark orange.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Furacilin darkens on prolonged exposure to light. Furacilin can react violently with reducing materials. .

Fire Hazard

Flash point data for Furacilin are not available; however, Furacilin is probably combustible.

Pharmaceutical Applications

A synthetic compound used in the topical treatment of wounds and burns and as an instillation for bladder washout. A nitrofurazone-impregnated urinary catheter is said to reduce infection in catheterized patients. Activity against the common bacterial pathogens is sufficient to cover most pathogens that cause infections of burns and wounds, with the important exception of Ps. aeruginosa. Attention has been drawn to its activity against methicillin-resistant Staphylococcus aureus, and its use in clearing carriage has been suggested. Slight absorption occurs from intact skin (c. 1%) and burned skin (5%). It is neither a primary irritant nor a sensitizer, but some preparations contain polyethylene glycol as a vehicle, and absorption can cause problems in patients with reduced renal function. Of limited availability.

Contact allergens

Nitrofurazone is an antibacterial agent used in animal feeds. Occupational dermatitis was reported in cattle breeders or farmers.

Clinical Use

5-Nitro-2-furaldehyde semicarbazone (Furacin) occurs asa lemon-yellow crystalline solid that is sparingly solublein water and practically insoluble in organic solvents.Nitrofurazone is chemically stable, but moderately lightsensitive.It is used topically in the treatment of burns, especiallywhen bacterial resistance to other agents may be a concern.It may also be used to prevent bacterial infection associatedwith skin grafts. Nitrofurazone has a broad spectrumof activity against Gram-positive and Gram-negative bacteria,but it is not active against fungi. It is bactericidalagainst most bacteria commonly causing surface infections,including S. aureus, Streptococcus spp., E. coli,Clostridium perfringens, Enterobacter (Aerobacter) aerogenes,and Proteus spp.; however, P. aeruginosa strainsare resistant.Nitrofurazone is marketed in solutions, ointments, andsuppositories in a usual concentration of 0.2%.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Questionable carcinogen with experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data, Experimental reproductive effects. A human sensitizer. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Nitrofurazone is the semicarbazone 5-nitrofurfurol (33.3.1). It is synthesized by reacting 5-nitrofurfurol with semicarbazide.

Synthesis_59-87-0

Veterinary Drugs and Treatments

Nitrofurazone can be used topically as an antibacterial for treating or preventing superficial infections. It is a nitrofuran antibacterial that is bactericidal for many bacteria, including E. Coli, Staph aureus, etc. Nitrofurazone’s mechanism of action is thought to be associated with inhibiting bacterial enzymes that primarily degrade glucose and pyruvate.

Nitrofurazone Preparation Products And Raw materials

Global( 398)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
+8613288715578 sales@hbmojin.com China 12452 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5990 58
Zibo Shiji Zhonglian Medical Technology Co., Ltd.
15069388126 15069388126 sales@sjzlpharm.com China 61 58
Anhui Yiao New Material Technology Co., Ltd
+86-199-55145978 +8619955145978 sales8@anhuiyiao.com China 253 58
Sigma Audley
+86-18336680971 +86-18126314766 nova@sh-teruiop.com China 524 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 - 03@ sales03@shyrchem.com CHINA 738 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682 bruce@xrdchem.cn CHINA 566 55
Anhui Royal Chemical Co., Ltd.
+86-25-86655873 +8613962173137 marketing@royal-chem.com China 535 55
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679 +86-18949832763 info@tnjchem.com China 2989 55

View Lastest Price from Nitrofurazone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Nitrofurazone pictures 2024-03-12 Nitrofurazone
59-87-0
US $35.00-25.00 / kg 1kg 99.8% 200tons/year Sigma Audley
Nitrofural pictures 2023-11-02 Nitrofural
59-87-0
US $0.00 / kg 1kg 99% 1 tons Anhui Yiao New Material Technology Co., Ltd
Nitrofural pictures 2023-11-02 Nitrofural
59-87-0
US $0.00 / kg 1kg 99% 1 tons Anhui Yiao New Material Technology Co., Ltd
  • Nitrofural pictures
  • Nitrofural
    59-87-0
  • US $0.00 / kg
  • 99%
  • Anhui Yiao New Material Technology Co., Ltd
  • Nitrofural pictures
  • Nitrofural
    59-87-0
  • US $0.00 / kg
  • 99%
  • Anhui Yiao New Material Technology Co., Ltd
2-Furaldehyde, 5-nitro-, semicarbazone 2-Furancarboxaldehyde, 5-nitro-, semicarbazone 5-Nitro-2-furaldehyde semicarbazole 5-nitro-2-furaldehydsemicarbazone 5-Nitro-2-furancarboxaldehyde semicarbazone 5-nitro-2-furancarboxaldehydesemicarbazone 5-Nitro-2-furfuraldehyde semicarbazone 5-nitro-2-furfuraldehydesemicarbazone 5-Nitrofuraldehyde semicarbazide 5-nitrofuraldehydesemicarbazide 5-Nitrofuran-2-aldehyde semicarbazone Fedacin Flavazone Fracine Furacine furacin-e Furacinetten Furacin-Hc Furacoccid Furacort Furacycline Furaderm Furagent Furalcyn Furaldon Furalone Furametral Furan-Ofteno Furaplast Furaseptyl Furaskin Furatsilin Furaziline Furazin Furazina Furazol W furazolw Furazyme Furesol Furosem Fuvacillin Hemofuran Hydrazinecarboxamide, 2-[(5-nitro-2-furanyl)methylene]- Ibiofural Mammex Mastofuran Monafuracin Monafuracis Monofuracin NCI-C56064 Nefco NF-7 Nfz mix Nifucin Nifurid Nifuzon Nitrofuraldehyde semicarbazone nitrofuraldehydesemicarbazone