5-Nitro-2-furfurolsemicarbazon

Bezeichnung:5-Nitro-2-furfurolsemicarbazon

CAS-Nr59-87-0

Englisch Name:Nitrofurazone

CBNumberCB0492724

SummenformelC6H6N4O4

Molgewicht198.14

MOL-Datei59-87-0.mol

Synonyma

5-Nitro-2-furfurolsemicarbazon

Nitrofural

5-Nitro-2-furfurolsemicarbazon physikalisch-chemischer Eigenschaften

Schmelzpunkt	242-244 °C (lit.)
Siedepunkt	335.43°C (rough estimate)
Dichte	1.6031 (rough estimate)
Brechungsindex	1.6500 (estimate)
Flammpunkt	2 °C
storage temp.	2-8°C
Löslichkeit	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)
Aggregatzustand	Solid
Farbe	Yellow to Dark Yellow
Wasserlöslichkeit	<0.1 g/100 mL at 19 ºC
Sensitive	Light Sensitive
Merck	14,6600
BRN	86403
InChIKey	IAIWVQXQOWNYOU-FPYGCLRLSA-N
CAS Datenbank	59-87-0(CAS DataBase Reference)
IARC	3 (Vol. 50) 1990
NIST chemische Informationen	5-Nitro furfural semicarbazone(59-87-0)
EPA chemische Informationen	Nitrofurazone (59-87-0)

Sicherheit

Kennzeichnung gefährlicher	Xn,F
R-Sätze:	22-36-20/21/22-11
S-Sätze:	36-36/37-26-16
RIDADR	3249
WGK Germany	3
RTECS-Nr.	LT7700000
F	8
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29321900
Giftige Stoffe Daten	59-87-0(Hazardous Substances Data)
Toxizität	LD50 in rats (g/kg): 0.59 orally; 3.0 s.c. (Godwin)

Gefahreninformationscode (GHS)

Nitrofurazone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Nitrofurazone is an antibacterial agent used in animal feed. Occupational dermatitis was reported in cattle breeders and farmers.
Chemische Eigenschaften
white to light yellow crystal powde
Originator
Furacin,Norwich Eaton ,US,1946
Verwenden
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.
Verwenden
Anti-infective (topical). Antimicrobial.Environmental contaminants; Food contaminants; Heat processing contaminants
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.
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.
Trademarks
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
Weltgesundheitsorganisation (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.
Allgemeine Beschreibung
Odorless pale yellow needles or yellow powder. pH (saturated aqueous solution) 6.0 - 6.5. Alkaline solutions are dark orange.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Furacilin darkens on prolonged exposure to light. Furacilin can react violently with reducing materials. .
Brandgefahr
Flash point data for Furacilin are not available; however, Furacilin is probably combustible.
Pharmazeutische Anwendungen
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.
Kontakt-Allergie
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%.
Sicherheitsprofil
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.
Synthese
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.

Nitrofurazone Upstream-Materialien And Downstream Produkte

5-Nitro-2-furfurolsemicarbazon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

59-87-0, Nitrofurazone Verwandte Suche:

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