Nitrofurantoin, gelbes Pulver
Lieferant: ICN Biomedicals
Synonyms:
1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione
, 1-[(5-Nitrofurfurylidene)amino]hydantoin
Nitrofurantoin is an antibactericidal compound that has been historically prepared by the reaction of 1-aminohydantoin sulphate and 5-nitro-2-furaldehyde diacetate.
It shows activity against many gram positive and gram-negative bacteria. Nitrofurantoin is effective against enterococci, staphylococci, streptococci, corney bacteria, many strains of escherichia coli. By contrast, most strains of proteus spp. and pseudomonas aeurginosa are more resistant to this compound. Other microbial species whose susceptibility to nitrofurantoin has been studied include plesiomonas shigelloide, campylobacter, and providencia.
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 metabolised 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 H2O2. 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.
Soluble in dimethylformamide (50 mg/ml - clear yellow to yellow-green solution), water, ethanol, acetone, peanut oil, glycerol, polyethylene glycol.
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Formel:
C₈H₆N₄O₅ MW: 238,16 g/mol Lager Temperatur: Raumtemperatur |
MDL Number:
MFCD00003224 CAS-Nummer: 67-20-9 |
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