Nitrofurazone Chemical 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)

NIST Chemistry Reference

5-Nitro furfural semicarbazone(59-87-0)

IARC

3 (Vol. 50) 1990

EPA Substance Registry System

Nitrofurazone (59-87-0)

Safety Information

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

F 

8

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29321900

Hazardous Substances Data

59-87-0(Hazardous Substances Data)

Toxicity

LD50 in rats (g/kg): 0.59 orally; 3.0 s.c. (Godwin)

MSDS

• Language:English Provider:Furacilin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Nitrofurazone Usage And Synthesis

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

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

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.

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

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.

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.

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.

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