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N7878 Sigma-Aldrich

Nitrofurantoin

crystalline

Synonym: N-(5-Nitro-2-furfurylidene)-1-aminohydantoin, Furadoxyl, Nitrofurantoine

  • CAS Number 67-20-9

  • Empirical Formula (Hill Notation) C8H6N4O5

  • Molecular Weight 238.16

  •  Beilstein/REAXYS Number 893207

  •  EC Number 200-646-5

  •  MDL number MFCD00003224

  •  PubChem Substance ID 24897842

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Mechanism of Action,
InChI Key   NXFQHRVNIOXGAQ-YCRREMRBSA-N
form   crystalline
color   yellow
solubility   DMF: soluble 50 mg/mL
Mode of action   DNA synthesis | interferes
  cell wall synthesis | interferes
  protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria

Description

Application

Nitrofurantoin is a nitrofuran antibiotic that is used as a substrate of 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 antibiotic resistance.Nitrofurantoin is suitable for killing L. monocytogenes-persisters in vitro. Studies has described the use of antioxidants to mitigate the toxic effects of nitrofurantoin on human WI-38 fibroblasts in culture. Alterations to the in vitro morphologic features, viability, and phagocytic activity of isolated bovine mammary polymorphonuclear leukocytes caused by various antibiotics, including nitrofurantoin, have been reported.

Packaging

10, 25, 100, 250 g in glass bottle

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Light sensitive.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
1
RTECS 
MU2800000

Documents

Certificate of Analysis

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Certificate of Origin

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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