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Nitrofurazone

Product Name
Nitrofurazone
CAS No.
59-87-0
Chemical Name
Nitrofurazone
Synonyms
NFS;NF;semicarbazone;NITROFURAL;FURACILIN;5-NITRO-2-FURALDEHYDE SEMICARBAZONE;Actin-N;FURACIN;Furazone;Furfurin
CBNumber
CB0492724
Molecular Formula
C6H6N4O4
Formula Weight
198.14
MOL File
59-87-0.mol
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Nitrofurazone Property

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)
form 
Solid
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)
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Safety

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
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

H341Suspected of causing genetic defects

H351Suspected of causing cancer

H373May cause damage to organs through prolonged or repeated exposure

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0002295
Product name
Nitrofural for peak identification A
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0002295
Price
$161
Updated
2024/03/01
Sigma-Aldrich
Product number
1465004
Product name
Nitrofurazone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
N0200
Product name
Nitrofurazone
Purity
>98.0%(HPLC)(E)
Packaging
25g
Price
$19
Updated
2024/03/01
TCI Chemical
Product number
N0200
Product name
Nitrofurazone
Purity
>98.0%(HPLC)(E)
Packaging
250g
Price
$91
Updated
2024/03/01
Alfa Aesar
Product number
A18593
Product name
5-Nitro-2-furaldehyde semicarbazone, 98+%
Packaging
25g
Price
$27.65
Updated
2024/03/01
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Nitrofurazone Chemical Properties,Usage,Production

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.

Nitrofurazone Preparation Products And Raw materials

Raw materials

Preparation Products

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Nitrofurazone Suppliers

Zouping Mingxing Chemical Co.,Ltd.
Tel
86-13605431940 13605431940
Fax
0086-0543-2240079
Email
zpmxchemical@126.com
Country
China
ProdList
1999
Advantage
62
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Capot Chemical Co., Ltd
Tel
+86 (0) 571 85 58 67 18
Fax
0086-571-85864795
Email
sales@capotchem.com
Country
China
ProdList
18207
Advantage
66
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
XiaoGan ShenYuan ChemPharm co,ltd
Tel
15527768850
Email
1791901229@qq.com
Country
China
ProdList
8836
Advantage
52
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View Lastest Price from Nitrofurazone manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Nitrofurazone 59-87-0
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-30
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Nitrofurazone 59-87-0
Price
US $0.00/Kg/Drum
Min. Order
25KG
Purity
97.0~103.0%; BP2015
Supply Ability
35tons/month
Release date
2021-06-08
Baoji Guokang Bio-Technology Co., Ltd.
Product
Nitrofurazone 59-87-0
Price
US $29.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20T
Release date
2021-06-02

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