Furazolidon

Furazolidone Struktur
67-45-8
CAS-Nr.
67-45-8
Bezeichnung:
Furazolidon
Englisch Name:
Furazolidone
Synonyma:
Furazolidon;Furoxane;3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone;Furoxone;Furazolidine;N-(5-NITRO-2-FURFURYLIDENE)-3-AMINO-2-OXAZOLIDIN-2-ONE;3-[[(5-Nitrofuran-2-yl)methylene]amino]oxazolidin-2-one;Furox;Neftin;NF 180
CBNumber:
CB8452405
Summenformel:
C8H7N3O5
Molgewicht:
225.16
MOL-Datei:
67-45-8.mol

Furazolidon Eigenschaften

Schmelzpunkt:
254-256°C (dec.)
Siedepunkt:
366.66°C (rough estimate)
Dichte
1.5406 (rough estimate)
Brechungsindex
1.7180 (estimate)
Flammpunkt:
2 °C
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit
formic acid: soluble50mg/mL
pka
-1.98±0.20(Predicted)
Aggregatzustand
powder
Farbe
yellow
maximale Wellenlänge (λmax)
365nm(DMSO)(lit.)
Sensitive 
Light Sensitive
Merck 
14,4300
BRN 
8317414
Stabilität:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
PLHJDBGFXBMTGZ-UITAMQMPSA-N
IARC
3 (Vol. 31, Sup 7) 1987
NIST chemische Informationen
Furazolidone(67-45-8)
EPA chemische Informationen
Furazolidone (67-45-8)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,F
R-Sätze: 62-40-36-20/21/22-11-68
S-Sätze: 36-22-36/37-16
WGK Germany  3
RTECS-Nr. RQ3675000
TSCA  Yes
HS Code  29349990
Giftige Stoffe Daten 67-45-8(Hazardous Substances Data)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

Furazolidon Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R62:Kann möglicherweise die Fortpflanzungsfähigkeit beeinträchtigen.
R40:Verdacht auf krebserzeugende Wirkung.

S-Sätze Betriebsanweisung:

S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S22:Staub nicht einatmen.

Beschreibung

Furazolidone belongs to the group of nitro furans. This antimicrobal (antibacterial and antiprotozoal) agent is used in veterinary medicine both topically and orally, particularly in animal feed. Reactions have been reported in workers exposed to it by contact with animal feed. Cross reactions with other nitrofuran derivatives are rare.

Chemische Eigenschaften

solid

Verwenden

The minimum inhibitory concentration of furazolidone was assessed to study the nonreplicating persistence of M. tuberculosis in aerobic and anaerobic conditions using luminescence-based low-oxygen-recovery assay.

Definition

ChEBI: A member of the class of oxazolidines that is 1,3-oxazolidin-2-one in which the hydrogen attached to the nitrogen is replaced by an N-{[(5-nitro-2-furyl)methylene]amino} group. It has antibacterial and antiprotozoal properties, and is us d in the treatment of giardiasis and cholera.

Weltgesundheitsorganisation (WHO)

Furazolidone, a nitrofuran derivative with antibacterial and antiprotozoal activity, was introduced in 1954. In the 1970s it was shown to have a carcinogenic potential following long-term administration to experimental animals. However, the relevance of this to short-term therapy in man has not been established. The risk-benefit assessment varies and furazolidone remains widely available in many countries for the treatment of diarrhoea and enteritis.

Antimicrobial activity

It is active against a wide range of enteric pathogens, including Salmonella enterica, Shigella spp., enterotoxigenic Escherichia coli, Campylobacter jejuni, Aeromonas hydrophila, Plesiomonas shigelloides, Vibrio cholerae and V. parahaemolyticus. Yersinia enterocolitica is intrinsically resistant. Furazolidone is also active against the protozoa Giardia lamblia and Trichomonas vaginalis.

Acquired resistance

Acquired resistance has been observed in V. cholerae O1 and O139, S. enterica serotypes Typhi and Enteritidis, A. hydrophila and Shigella spp. Such resistance may be transferable, and there is cross-resistance with nitrofurantoin. Many of these reports come from the Indian subcontinent, where furazolidone is used widely for treating diarrheal diseases.

Allgemeine Beschreibung

Furazolidone is an effective antiprotozoal and antibacterial agent.

Hazard

A questionable carcinogen, use has been restricted.

Pharmazeutische Anwendungen

A non-ionic synthetic compound, available for oral use only. It is poorly soluble in water (40 mg/L) and ethanol (90 mg/L), but dissolves well in dimethylformamide (10 g/L). It decomposes in the presence of alkali.

Kontakt-Allergie

Furazolidone belongs to the group of nitrofurans. This antimicrobial (antibacterial and antiprotozoal) agent is used in veterinary medicine both topically and orally, particularly in animal feed. Reactions are reported in workers exposed to it in animal feeds. Cross-reactions with other nitrofuran derivatives are rare.

Pharmakokinetik

There is substantial absorption (65–70%) after oral administration, but the drug is heavily metabolized, so that only about 5% of the material excreted is microbiologically active. A dose of 5 mg/kg achieves a maximum plasma concentration of around 1 mg/L. Protein binding is about 30%. Intact drug can be found in various body fluids in concentrations approximating to the minimum inhibitory concentration (MIC) for various intestinal pathogens. Less than 1% of the drug is excreted into urine.

Clinical Use

Furazolidone is used in gastrointestinal infections and vaginitis. It is mainly used in developing countries to treat diarrheal diseases of varying etiology, but it is not the drug of choice if a specific pathogen has been identified. Use as a secondline agent in giardiasis and as part of multidrug regimens in Helicobacter infection has been advocated.

Nebenwirkungen

Most reported side effects are mild and only rarely cause discontinuation of treatment. Nausea and vomiting are experienced by around 8% of patients. Other adverse events include neurological reactions (mainly headache; 1.3% of patients), ‘systemic’ reactions such as fever and malaise (0.6%) and skin rashes (0.54%). Administration of furazolidone may give rise to inhibition of monoamine oxidase, and disulfiram-like reactions have been reported.

Sicherheitsprofil

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: dyspnea, respiratory depression, and eosinophilta. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NOx.

Furazolidon Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Furazolidon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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67-45-8(Furazolidon)Verwandte Suche:


  • 2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)-
  • 2-Oxazolidinone, 3-((5-nitrofurfurylidene)amino)-
  • 2-Oxazolidinone, 3-((5-nitrofurfurylidine)amino)-
  • 2-Oxazolidinone, 3-[[(5-nitro-2-furanyl)methylene]amino]-
  • 2-Oxazolidinone,3-[[(5-nitro-2-furanyl)methylene]amino]-
  • 3-(((5-nitro-2-furanyl)methylene)amino)-2-oxazolidinon
  • Furaxon
  • Furaxone
  • Furazol
  • furazolidone(notsubjectto
  • furazolidone(notsubjecttofifra:8709-e
  • furazolidone(notsubjecttofifra:8709-epm24)
  • Furazon
  • Furidon
  • Furovag
  • Furox
  • Furoxal
  • Furoxon
  • Furoxone Swine Mix
  • furoxoneswinemix
  • Furozolidine
  • Giardil
  • Giarlam
  • Medaron
  • N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone
  • N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-one
  • Neftin
  • NF 180
  • NF 180 custom mix ten
  • nf-180
  • FURAZOLIDONE BP / USP
  • FURAZOLIDONE BP 98
  • foroxone
  • 3-(5-Nitrofurfurylideneamino)-2-oxazolidione
  • FURAZOLIDONE VETRANAL, 250 MG
  • Furazolidone,98%
  • FURAZOLIDONE,USP
  • 3-(5-NITROFURFURYLIDENEAMINO)OXAZOLIDIN-2-ONE(FURAZOLIDONE)
  • FURAZIDIN(FURAGIN)
  • 3-(5-Nitrofurfurylideneamino)oxazolidin-2-one
  • Furanzolidone
  • 3-(5-Nitrofurfurylideneamino)-4,5-dihydrooxazol-2(3H)-one
  • 3-[[(5-Nitrofuran-2-yl)methylene]amino]oxazolidine-2-one
  • Furazolidone,3-(5-Nitrofurfurylideneamino)-2-oxazolidinone
  • Furazolidone (200 mg)
  • 1-(furan-2-yl)pyrrolidin-2-one
  • Furazolldone
  • 3-((5-nitrofurfurylidene)amino)-2-oxazolidinon
  • 3-((5-Nitrofurfurylidene)amino)-2-oxazolidone
  • 3-((5-Nitrofurylidene)amino)-2-oxazolidone
  • 3-([(E)-(5-Nitro-2-furyl)methylidene]amino)-1,3-oxazolidin-2-one
  • Furazolidone solution,100ppm
  • Furazolidone Vetec(TM) reagent grade
  • FurazolidoneUSP, 97-103% (Assay)
  • 3-(5-NITROFURFURYLIDENEAMINO)-2-OXAZOLIDINONE
  • 3-(5-NITROFURYLIDENEAMINO)-2-OXAZOLIDINONE
  • LABOTEST-BB LT00244769
  • 3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinon
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