59-87-0 Usage
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
Different sources of media describe the Uses of 59-87-0 differently. You can refer to the following data:
1. Anti-infective (topical). Antimicrobial.Environmental contaminants; Food contaminants; Heat processing contaminants
2. Anti-infective (topical). Antimicrobial.
3. 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
Different sources of media describe the Definition of 59-87-0 differently. You can refer to the following data:
1. 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.
2. 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.
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.
Biological evaluation of arylsemicarbazone derivatives as potential anticancer agents
da Cruz, Anne Cecília Nascimento,Brondani, Dalci José,de Santana, Temístocles I′Talo,da Silva, Lucas Oliveira,Borba, Elizabeth Fernanda da Oliveira,de Faria, Ant?nio Rodolfo,de Albuquerque, Julianna Ferreira Cavalcanti,Piessard, Sylvie,Ximenes, Rafael Matos,Baratte, Blandine,Bach, Stéphane,Ruchaud, Sandrine,Mendon?a Junior, Francisco Jaime Bezerra,Bazin, Marc-Antoine,Rabello, Marcelo Montenegro,Hernandes, Marcelo Zaldini,Marchand, Pascal,da Silva, Teresinha Gon?alves
, (2019/11/25)
Fourteen arylsemicarbazone derivatives were synthesized and evaluated in order to find agents with potential anticancer activity. Cytotoxic screening was performed against K562, HL-60, MOLT-4, HEp-2, NCI-H292, HT-29 and MCF-7 tumor cell lines. Compounds 3c and 4a were active against the tested cancer cell lines, being more cytotoxic for the HL-60 cell line with IC50 values of 13.08 μμM and 11.38 μμM, respectively. Regarding the protein kinase inhibition assay, 3c inhibited seven different kinases and 4a strongly inhibited the CK1δ/ε kinase. The studied kinases are involved in several cellular functions such as proliferation, migration, cell death and cell cycle progression. Additional analysis by flow cytometry revealed that 3c and 4a caused depolarization of the mitochondrial membrane, suggesting apoptosis mediated by the intrinsic pathway. Compound 3c induced arrest in G1 phase of the cell cycle on HL-60 cells, and in the annexin V assay approximately 50% of cells were in apoptosis at the highest concentration tested (26 μμM). Compound 4a inhibited cell cycle by accumulation of abnormal postmitotic cells at G1 phase and induced DNA fragmentation at the highest concentration (22 μμM).
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.
