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Nitrofurantoin is a nitrofuran antibiotic that is used as a substrate for bacterial nitrofuran reductase to study the interactions of active metabolites with DNA, ribosomal proteins and metabolic and pro-oxidant processes. It is used to study nitrofurantoin - induced toxicity and antiobiotic resistance.
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|Alternate Names||N-(5-Nitro-2-furfurylidene)-1-aminohydantoin;Furadoxyl; Nitrofurantoine|
|Application Notes||Nitrofurantoin is a nitrofuran antibiotic that is used as a substrate for bacterial nitrofuran reductase to study the interactions of active metabolites with DNA, ribosomal proteins and metabolic and pro-oxidant processes. It is used to study nitrofurantoin - induced toxicity and antiobiotic resistance.|
|Base Catalog Number||155881|
|Beilstein Registry Number||893207|
|Biochemical Physiological Actions||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 H2O 2. 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.|
|Extinction Coefficient||E1% = 776 (H2O) (Lit.)|
|Melting Point||514° F (decomposes) (NTP, 1992)|
|Molecular Weight||238.159 g/mol|
|Personal Protective Equipment||Dust mask, Eyeshields, Faceshields, Gloves|
|Safety Symbol||GHS07, GHS08|