59-87-0 Usage
Description
Furacilin, also known as Nitrofurazone, is an organic compound containing the C:N.NH.CO.NH2 grouping. It is formed by the reaction of an aldehyde or ketone with semicarbazide and is characterized by its crystalline solid structure and sharp melting points. Furacilin is an odorless pale yellow needle or yellow powder with a pH of 6.0 6.5 in its saturated aqueous solution. Alkaline solutions of Furacilin appear dark orange.
Uses
Used in Pharmaceutical Industry:
Furacilin is used as an anti-infective and antimicrobial agent for various applications, including the treatment or prevention of infections in skin, eyes, ears, nose, and genito-urinary tract. It is effective against most pathogens commonly causing surface infections and is particularly useful in the adjunctive therapy of patients with second and third-degree burns when bacterial resistance to other agents is a real or potential problem.
Used in Veterinary Medicine:
Furacilin is used as an antibacterial agent in animal feed, helping to prevent and treat infections in livestock. It is also used as an antiseptic lubricant for transurethral resection and as an anti-microbial agent in veterinary medicine.
Used in Environmental and Food Contaminant Control:
Furacilin is employed to combat environmental contaminants and food contaminants, helping to maintain hygiene and prevent the spread of infections in various settings.
Used in Skin Graft Procedures:
Furacilin is used in skin grafting procedures to prevent bacterial contamination, which may cause graft rejection and/or donor-site infection.
Used in Topical Applications:
Furacilin is used topically for the treatment of pyodermas, ulcers, and wounds, as well as for its effects on some protozoa. It also serves as an effective prophylaxis against nosocomial infections.
Brand Names:
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, Furaseptin, Fura-septin, Fura-vet, Furea, Furesan, Furotalgin, Furovol, Germax, Ginejuvent, I fomula, Ii formula, Kamfomen, Kindrog, Lifuzol, Mammiject, Mastidol, Muldacin, Novagon, Nfz 1, Nitocetin, Nitrocol plus, Nitro-rea, Notaba, Sanifur, Scandantin, Sulfamyton-n, Taristop, Tranoxa, Tuocurine, Urafadyn, Uroletten, Viropulver, Yalrocin, and Zoppin spray blu.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 59-87-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 59-87:
(4*5)+(3*9)+(2*8)+(1*7)=70
70 % 10 = 0
So 59-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+
59-87-0Relevant articles and documents
Pharmacokinetics of hydroxymethylnitrofurazone, a promising new prodrug for chagas' disease treatment
Serafim, Eliana Ometto Pavan,De Albuquerque E Silva, Antonio Tavora,De Haro Moreno, Andreia,De Oliveira Vizioli, Ednir,Ferreira, Elizabeth Igne,Peccinini, Rosangela Goncalves,Ribeiro, Maria Lucia,Chung, Man Chin
, p. 6106 - 6109 (2013)
Hydroxymethylnitrofurazone (NFOH) is a trypanocidal prodrug of nitrofurazone (NF), devoid of mutagenic toxicity. The purpose of this work was to study the chemical conversion of NFOH into NF in sodium acetate buffer (pH 1.2 and 7.4) and in human plasma and to determine preclinical pharmacokinetic parameters in rats. At pH 1.2, the NFOH was totally transformed into NF, the parent drug, after 48 h, while at pH 7.4, after the same period, the hydrolysis rate was 20%. In human plasma, 50% of NFOH was hydrolyzed after 24 h. In the investigation of kinetic disposition, the concentration of drug in serum versus time curve was used to calculate the pharmacokinetic parameters after a single-dose regimen. NFOH showed a time to maximum concentration of drug in serum (Tmax) as 1 h, suggesting faster absorption than NF (4 h). The most important results observed were the volume of distribution (V) of NFOH through the tissues, which showed a rate that is 20-fold higher (337.5 liters/kg of body weight) than that of NF (17.64 liters/kg), and the concentration of NF obtained by in vivo metabolism of NFOH, which was about four times lower (maximum concentration of drug in serum [Cmax]=0.83 μg/ml; area under the concentration-time curve from 0 to 12 h [AUC0-12]=5.683 μg/ml · h) than observed for administered NF (Cmax=2.78 μg/ml; AUC0-12=54.49 μg/ml · h). These findings can explain the superior activity and lower toxicity of the prodrug NFOH in relation to its parent drug and confirm NFOH as a promising anti-Chagas' disease drug candidate. Copyright
-
Sanders et al.
, p. 358,359 (1955)
-
Nitrofuran drugs beyond redox cycling: Evidence of Nitroreduction-independent cytotoxicity mechanism
Gallardo-Garrido,Cho,Cortés-Rios,Vasquez,Pessoa-Mahana,Araya-Maturana,Pessoa-Mahana,Faundez
, (2020/06/23)
Nitrofurans (5-nitro-2-hydrazonylfuran as pharmacophore) are a group of widely used antimicrobial drugs but also associated to a variety of side effects. The molecular mechanisms that underlie the cytotoxic effects of nitrofuran drugs are not yet clearly understood. One-electron reduction of 5-nitro group by host enzymes and ROS production via redox cycling have been attributed as mechanisms of cell toxicity. However, the current evidence suggests that nitrofuran ROS generation by itself is uncapable to explain the whole toxic effects associated to nitrofuran consumption, proposing a nitro-reduction independent mechanism of toxicity. In the present work, a series of nitrated and non-nitrated derivatives of nitrofuran drugs were synthesized and evaluated in vitro for their cytotoxicity, ROS-producing capacity, effect on GSH-S-transferase and antibacterial activity. Our studies showed that in human cells non-nitrated derivatives were less toxic than parental drugs but, unexpectedly preserved the ability to generate intracellular ROS in similar amounts to nitrofurans despite not entering into a redox cycle mechanism. In addition, some non-nitrated derivatives although being uncapable to generate ROS exhibited the highest cell toxicity among all derivatives. Inhibition of cytosolic glutathione-S-transferase activity by some derivatives was also observed. Finally, only nitrofuran derivatives displayed antibacterial effect. Results suggest that the combined 2-hydrazonylfuran moiety, redox cycling of 5-nitrofuran, and inhibitory effects on antioxidant enzymes, would be finally responsible for the toxic effects of the studied nitrofurans on mammalian cells.
A general and convenient synthesis of 4-(tosylmethyl)semicarbazones and their use in amidoalkylation of hydrogen, heteroatom, and carbon nucleophiles
Fesenko, Anastasia A.,Yankov, Alexander N.,Shutalev, Anatoly D.
, (2019/10/14)
A general synthesis of previously unknown semicarbazone-based α-amidoalkylating reagents, 4-(tosylmethyl)semicarbazones, has been developed. The synthesis involved three-component condensation of semicarbazones of aliphatic or aromatic aldehydes with the same or other aldehydes and p-toluenesulfinic acid. The scope and limitations of this reaction were investigated. The compounds obtained were demonstrated to be an efficient α-(4-semicarbazono)alkylating agents. They were reacted with H- (sodium borohydride), O- (sodium methylate), S- (sodium phenylthiolate), N- (pyrrolidine, sodium succinimide), P- (trialkyl phosphites), and C-nucleophiles (sodium diethyl malonate) to give the corresponding products of the tosyl group substitution, 4-substituted semicarbazones, including analogues of nitrofurazone. Among the prepared compounds tested in vitro for antibacterial and antifungal activity, three nitrofuryl-containing semicarbazones exhibited high biological activities with minimum inhibitory concentration (MIC) values of 8–32 μg/mL.
Synthesis, properties, and application of 4-nitrosemicarbazones
Glukhacheva,Il’yasov,Sakovich,Tolstikova,Bryzgalov,Pleshkova
, p. 550 - 560 (2017/03/08)
The studies of the condensation of 4-nitrosemicarbazide (4-NSC) with various aldehydes and ketones resulted in the development of an approach to the synthesis of N-nitrosemicarbazones, promising high-energy and biologically active compounds. Subsequent treatment with amines and alkalis led to the synthesis of water-soluble salts of nitrosemicarbazones, as well as the corresponding semicarbazones. The reaction of N,N′-diisopropyl- or N,N′-di-tert-butyl-1,2-ethanediimine with 4-nitrosemicarbazide led to the synthesis of glyoxal bis(nitrosemicarbazone) derivatives. A computer-aided screening using the PASS software showed a probability of high biological activity for the compounds obtained, whereas antiarrhythmic properties of camphor nitrosemicarbazone potassium salt were confirmed in experiments in rats.