1-(((5-Nitro-2-furanyl)methylen)-amino)-2,4-imidazolidindion 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
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.
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.
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.
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.
Clinical Use
Acute dysuria and frequency
Bacteriuria in pregnancy
Prophylaxis of recurrent cystitis (reduced dosage)
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.
1-(((5-Nitro-2-furanyl)methylen)-amino)-2,4-imidazolidindion Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
