• Product NameNitrofurazone
  • CasNo. 59-87-0
  • MFC6H6N4O4
  • MW198.138
  • Purity
  • Appearancewhite to light yellow crystal powder
  • Packing
  • Contact usInquiry

Product Details

CasNo: 59-87-0

MF: C6H6N4O4

Appearance: white to light yellow crystal powder

Offer Chemical Raw Material Nitrofurazone 59-87-0 In Stock

  • Molecular Formula:C6H6N4O4
  • Molecular Weight:198.138
  • Appearance/Colour:white to light yellow crystal powder 
  • Melting Point:242-244 °C(lit.) 
  • Refractive Index:1.674 
  • Boiling Point:236-240oC 
  • PKA:pKa 9.28± 0.03( EtOH,t =35±0.1,I=0.00) (Uncertain) 
  • Flash Point:2 °C 
  • PSA:126.44000 
  • Density:1.7 g/cm3 
  • LogP:1.80440 

Furacilin(Cas 59-87-0) Usage

Description

Nitrofurazone is an antimicrobial organic compound belonging to the nitrofuran class. It is a broad-spectrum antibacterial agent effective against both gram-positive and gram-negative bacteria.

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.

Contact allergens

Nitrofurazone is an antibacterial agent used in animal feeds. Occupational dermatitis was reported in cattle breeders or farmers.

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.

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.

Mechanism of action While the exact mechanism is not fully known, nitrofurazone is thought to work by inhibiting several bacterial enzymes, especially those involved in the breakdown of glucose and pyruvate. It does this by generating reactive intermediates through metabolic reduction of the nitro group which then bind to cellular macromolecules, interfering with essential bacterial processes like DNA synthesis.

Who Evaluation

Evaluation year: 1993

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+

59-87-0 Relevant articles

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 t...

ESR SPECTRA OF ELECTROCHEMICALLY GENERATED ANION RADICALS OF THE NITROFURAN SERIES

Gavars, R.,Stradins, J.,Baumane, L.,Baider, L.

, p. 183 - 198 (1983)

ESR spectra of anion radicals for 29 der...

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)

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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 unknow...

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 w...

Method for synthesizing furacilin under catalysis of supported catalyst

-

, (2018/06/26)

The invention discloses a method for syn...

59-87-0 Process route

5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

nitrofurazone
59-87-0

nitrofurazone

Conditions
Conditions Yield
semicarbazide hydrochloride; With sodium hydride; In dimethyl sulfoxide; for 5h;
5-nitrofurane-2-carboxaldehyde; In dimethyl sulfoxide; at 20 ℃; for 18h; Further stages.;
55%
With sodium acetate; In ethanol; water;
 
5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

nitrofurazone
59-87-0

nitrofurazone

Conditions
Conditions Yield
With methanol; 5-nitro-furfural semicarbazone of mp: 232 degree;
 
With ethanol; 5-nitro-furfural semicarbazone of mp: 232 degree;
 

59-87-0 Upstream products

  • 624-46-4
    624-46-4

    butan-2-one semicarbazone

  • 92-55-7
    92-55-7

    5-nitro-2-furfuraldehyde diacetate

  • 563-41-7
    563-41-7

    semicarbazide hydrochloride

  • 4426-72-6
    4426-72-6

    hydrazine carboxamide

59-87-0 Downstream products

  • 112537-96-9
    112537-96-9

    5-nitro-2-furaldehyde azine

  • 112574-40-0
    112574-40-0

    syn isomer of nitrofurazone

  • 518052-13-6
    518052-13-6

    Hydroxymethylnitrofurazone

  • 563-41-7
    563-41-7

    semicarbazide hydrochloride

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