1-(((5-Nitro-2-furanyl)methylen)-amino)-2,4-imidazolidindion

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H317：Kann allergische Hautreaktionen verursachen.

  H334：Kann bei Einatmen Allergie, asthmaartige Symptome oder Atembeschwerden verursachen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

Nitrofurantoin Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

• Chemische Eigenschaften

  lemon yellow crystalline powder

• Originator

  Furadantin,Norwich Eaton ,US,1953

• Verwenden

  counterirritant

• Verwenden

  A nitrofuran antibiotic with low resistance potential that is rapidly metabolized by mammals. Active against both Gram-positive and Gram-negative bacteria. Nitrofurantoin is also a prooxidant that is cytotoxic due to the generation of intracellular H2O2. Antibacterial.Environmental contaminants; Food contaminants; Heat processing contaminants

• Indications

  Like nitrofurazone, nitrofurantoin is an effective drug that acts on a number of Grampositive and Gram-negative microorganisms (staphylococci, streptococci, dysentery bacillus, colon bacillus, paratyphoid bacillus, and others). It is primarily used for treating infectious diseases of the urinary tract (pyelitis, pyelonephritis, cystitis, urethritis). Synonyms of this drug are furadonin, ituran, phenurin, urolong, cistofuran, nitrofurin, and many others.

• Definition

  ChEBI: An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.

• Manufacturing Process

  To a solution of 18.9 grams (0.166 mol) n-heptaldehyde in 25 ml of isopropanol is added, with stirring, a solution of 19.1 grams (0.166 mol) of 1aminohydantoin in 110 ml water acidified with concentrated HCl. The heavy white precipitate formed is filtered and washed, until acid free, with small amounts of water and ether. The yield of N-(n-heptylidene)-1-aminohydantoin is 14 grams of MP 150°C (with decomposition). This may be recrystallized from dimethylformamide.
  A mixture of 2.5 grams (0.016 mol) of 5-nitro-2-furaldoxime, 3.9 grams (0.018 mol) of N-(n-heptylidene)-1-aminohydantoin and 5 cc of sulfuric acid (density 1.84) is placed in a 250 cc beaker. It is heated with stirring at steam bath temperature for about 1.5 hours. Upon cooling, a solid precipitates which is collected by filtration, washed with water, isopropanol and ether in turn and dried at 110°C for 4 hours. There is obtained N-(5-nitro-2-furfurylidene)-1aminohydantoin in 96 to 98% yield, according to US Patent 2,927,110.

• Trademarks

  Ivadantin (Procter & Gamble);Furan;Nitrofan.

• Therapeutic Function

  Antibacterial (urinary)

• Antimicrobial activity

  It is active against almost all the common urinary pathogens, except Proteus mirabilis. It is bactericidal.
  It antagonizes the activity of nalidixic acid and other quinolones in vitro, but this combination is unlikely to be used clinically.

• Acquired resistance

  Surprisingly for an agent that has been used for so long, resistance remains uncommon. R-factor-mediated resistance has been reported, but this appears to be very unusual. The mechanism of resistance seems to be a decreased nitroreductase activity in the target organism.
  There is cross-resistance within the nitrofuran group, but none with antibiotics of other chemical classes.

• Allgemeine Beschreibung

  Odorless lemon yellow crystals or fine yellow powder. Bitter taste.

• Air & Water Reaktionen

  Insoluble in water.

• Reaktivität anzeigen

  Nitrofurantoin is sensitive to light. Nitrofurantoin is incompatible with alkalis. Nitrofurantoin is also incompatible with strong oxidizers and strong acids. Nitrofurantoin decomposes on contact with metals other than stainless steel and aluminum.

• Hazard

  Questionable carcinogen.

• Brandgefahr

  Flash point data for Nitrofurantoin are not available; however, Nitrofurantoin is probably combustible.

• Pharmazeutische Anwendungen

  A synthetic compound available only for oral administration. There are three formulations, differing in their crystalline nature: microcrystalline, macrocrystalline, and a delayedrelease preparation containing a combination of the two. The macrocrystalline form is said to be less liable to give rise to the most common adverse event, nausea. However, pharmacokinetic and clinical trial evidence for this assertion is not very strong.
  It is slightly soluble in water (c. 200 mg/L) but more so in dilute alkali. Solubility in ethanol is modest (500 mg/L), but the compound dissolves very well in dimethylformamide (80 g/L). If packaged in light-resistant containers and kept at room temperature, it is stable for more than 5 years. The yellow solution should be kept in the dark.

• Biochem/physiol Actions

  Nitrofurantoin is an antibactericidal compound that has been historically prepared by the reaction of 1-aminohydantoin sulfate and 5-nitro-2-furaldehyde diacetate. It shows activity against many Gram-positive and Gram-negative bacteria. Nitrofurantoin is effective against enterococci, staphylococci, streptococci, corneybacteria, many strains of Escherichia coli. Most strains of Proteus spp. and Pseudomonas aeurginosa are more resistant to this compound. Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to actively reduce reactive intermediates that modulate and damage ribosomal proteins or other macromolecules, such as DNA. This inhibits DNA, RNA, protein, and cell wall synthesis which causes cell death. Nitrofurantoin has a low resistance potential that is rapidly metabolized by mammals and is active against both Gram-positive and Gram-negative bacteria. It is also a pro-oxidant that is cytotoxic due to the generation of intracellular H 2O2. It is an inhibitor of glutathione reductase. Nitrofurantoin produces hepatotoxicity caused by the redox cycling of the nitro group and its radical anion which leads to oxidative stress.

• Pharmakokinetik

  Oral absorption:>95%
  C_max 100 mg oral: <2 mg/L after 1–4 h
  Plasma half-life:0.5–1 h
  Volume of distribution: 0.6 L/kg
  Plasma protein binding: 60–70%
  Absorption
  It is absorbed mainly from the proximal small intestine and the plasma peak concentration may not be achieved for as long as 4 h. The recommendation to take the drug with food may be motivated by reducing the incidence of nausea rather than increasing bioavailability.
  Bioavailability varies widely between different brands and this may not be apparent from results of standard in-vitro pharmaceutical tests. Therefore, different brands should not be substituted unless therapeutic equivalence has been formally established.
  Distribution
  Serum levels are low, owing to extensive metabolism and the short plasma half-life. Tissue concentrations are too low for adequate treatment of systemic infection, including pyelonephritis. Negligible concentrations are found in breast milk and only a small amount crosses the placenta.
  Metabolism and excretion
  About 20% of the dose is excreted in microbiologically active form in the urine, sufficient to give inhibitory concentrations against urinary pathogens for up to 6 h. With reduced renal function (creatinine clearance <60 mL/min), urinary excretion falls, and virtually ceases when creatinine clearance is below 20 mL/min. This gives rise to the risk of accumulation in the blood and inadequate urine levels. With this proviso, it can be given to elderly patients. Infants over the age of 3 months may also be treated, but in the absence of a suitable suspension, and at the recommended dosage, a 6-month baby would need to be given one-tenth of a standard 50 mg tablet.

• Clinical Use

  Acute dysuria and frequency
  Bacteriuria in pregnancy
  Prophylaxis of recurrent cystitis (reduced dosage)

• Nebenwirkungen

  Nausea, which may be combined with anorexia or vomiting, or both, occurs in about 30% of patients taking the microcrystalline form, causing about 10% to stop treatment. The frequency of nausea is approximately halved with the macrocrystalline formulation. Nausea is due to a direct effect on the vomiting center; it occurs early in the course, and its incidence may be reduced by taking the medication with food or milk.
  Pulmonary, hepatic, neurological and hematological side effects have been reported, but are very uncommon. There are two kinds of pulmonary reaction. Acute reactions are the more common, starting within 5–10 days of the first dose, or within a few hours on re-challenge. Symptoms may resemble those found in asthma, tracheobronchitis or pneumonia, and usually resolve permanently within 2 days. There may be an eosinophilia. Subacute or chronic reactions, often referred to as pneumonitis, are of more gradual onset, and resolve only slowly when the drug is stopped. Prolonged dyspnea and cough may be accompanied by fibrosis.
  Hepatic reactions follow prolonged drug usage and usually manifest as chronic active hepatitis, sometimes with cirrhosis. The prognosis is good, but recovery may take months. Peripheral neuropathy has been reported mainly in patients with pre-existing impaired renal function. The prognosis depends upon the severity of the symptoms. Unlike hepatic and pulmonary effects, for which immunological phenomena seem to be responsible, neurological events have been attributed to a direct toxic effect of the drug, one of its metabolites or the superoxide generated in vivo.
  In common with other nitrofurans, nitrofurantoin may cause hemolysis in patients who lack glucose-6-phosphate dehydrogenase.

• Sicherheitsprofil

  Poison by ingestion and intraperitoneal routes. Human systemic effects: peripheral motor nerve recording changes, ataxia, changes in urine composition, and hemolysis with or without anemia. Human reproductive effects by ingestion: spermatogenesis. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

• Synthese

  Nitrofurantoin, 1-(5-nitrofurfurylidenamino)hydantoin (33.3.5), is synthesized from hydrazinoacetic acid (33.3.2), which is synthesized by reacting chloroacetic acid with hydrazine. Reacting hydrazinoacetic acid with potassium cyanate gives the semicarbazidoacetic acid (33.3.3), which upon heating cyclizes into 1-aminoidantoin (33.3.4). Reacting this with diacetylacetal of 5-nitrofurfurol gives the desired nitrofurantoin.

  

• Veterinary Drugs and Treatments

  Considered a urinary tract antiseptic, nitrofurantoin is used primarily in small animals, but also occasionally in horses in the treatment of lower urinary tract infections caused by susceptible bacteria. It is not effective in treating renal cortical or perinephric abscesses or other systemic infections.

• Stoffwechsel

  Nitrofurantoin is metabolised in the liver and most body tissues, while about 30-40% of a dose is excreted rapidly in the urine as unchanged nitrofurantoin. Some tubular reabsorption may occur in acid urine.

Nitrofurantoin Upstream-Materialien And Downstream Produkte

1-(((5-Nitro-2-furanyl)methylen)-amino)-2,4-imidazolidindion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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