| Identification | More | [Name]
Furacilin | [CAS]
59-87-0 | [Synonyms]
2-[(5-nitro-2-furanyl)methylene]-hydrazinecarboxamide
5-NITRO-2-FURALDEHYDE SEMICARBAZONE
5-NITRO-2-FURFURAL SEMICARBAZONE
5-NITRO-2-FURFURYLIDENE SEMICARBAZONE
5-NITROFURFURAL SEMICARBAZONE
AKOS B004247
FURACILIN
FURACIN
LABOTEST-BB LT00134617
NFZ
NITROFURAL
NITROFURAZONE
(5-Nitro-2-furfurylidenamino)urea
(5-Nitro-2-furfurylideneamino)urea
1-(5-Nitro-2-furfurylidene)semicarbazide
1-(5-Nitrofurfurylidene)semicarbazide
2-((5-nitro-2-furanyl)methylene)-hydrazinecarboxamid
2-[(5-nitro-2-furanyl)methylene]-hydrazinecarboxamid
2-Furaldehyde, 5-nitro-, semicarbazone
2-Furancarboxaldehyde, 5-nitro-, semicarbazone | [EINECS(EC#)]
200-443-1 | [Molecular Formula]
C6H6N4O4 | [MDL Number]
MFCD00003225 | [Molecular Weight]
198.14 | [MOL File]
59-87-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
242-244 °C(lit.)
| [Boiling point ]
335.43°C (rough estimate) | [density ]
1.6031 (rough estimate) | [refractive index ]
1.6500 (estimate) | [Fp ]
2 °C | [storage temp. ]
2-8°C
| [solubility ]
Very slightly soluble in water, slightly soluble in ethanol (96 per cent). | [form ]
neat | [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 | [Contact allergens]
Nitrofurazone is an antibacterial agent used in animal
feeds. Occupational dermatitis was reported in cattle
breeders or farmers. | [InChIKey]
IAIWVQXQOWNYOU-FPYGCLRLSA-N | [CAS DataBase Reference]
59-87-0(CAS DataBase Reference) | [IARC]
3 (Vol. 50) 1990 | [NIST Chemistry Reference]
5-Nitro furfural semicarbazone(59-87-0) | [EPA Substance Registry System]
59-87-0(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
Anti-infective (topical). Antimicrobial. | [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. | [General Description]
Odorless pale yellow needles or yellow powder. pH (saturated aqueous solution) 6.0-6.5. Alkaline solutions are dark orange. | [Reactivity Profile]
NITROFURAZONE(59-87-0) darkens on prolonged exposure to light. This chemical can react violently with reducing materials. . | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this chemical are not available; however, NITROFURAZONE is probably combustible. | [Description]
Nitrofurazone is an antibacterial agent used in animal
feed. Occupational dermatitis was reported in cattle
breeders and farmers.
| [Originator]
Furacin,Norwich Eaton ,US,1946 | [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. | [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. | [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. | [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%. | [Synthesis]
Nitrofurazone is the semicarbazone 5-nitrofurfurol (33.3.1). It is synthesized by reacting 5-nitrofurfurol with semicarbazide.
| [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. | [storage]
Store at -20°C |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,F | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
LT7700000
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29321900 | [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. | [Hazardous Substances Data]
59-87-0(Hazardous Substances Data) | [Toxicity]
LD50 in rats (g/kg): 0.59 orally; 3.0 s.c. (Godwin) |
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