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.NH
2 grouping, formed by reaction of an aldehyde or ketone with semicarbazide (H2N.NH.CO.NH
2). 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.
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.
