N7878

Nitrofurantoin

98.0-102.0% (EP, UV)

• Synonym(s): N-(5-Nitro-2-furfurylidene)-1-aminohydantoin, Furadoxyl, Nitrofurantoine
• Empirical Formula (Hill Notation): C₈H₆N₄O₅
• CAS Number: 67-20-9
• Molecular Weight: 238.16
• Beilstein: 893207
• EC Number: 200-646-5
• MDL number: MFCD00003224
• UNSPSC Code: 51102829
• PubChem Substance ID: 24897842
• NACRES: NA.85

Properties

• Assay: 98.0-102.0% (EP, UV)
• form: (Crystalline Powder or crystals)
• color: yellow
• solubility: DMF: soluble 50 mg/mL
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria
• Mode of action: DNA synthesis | interferes; cell wall synthesis | interferes; protein synthesis | interferes
• SMILES string: [O-][N+](=O)c1ccc(\C=N\N2CC(=O)NC2=O)o1
• InChI: 1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
• InChI key: NXFQHRVNIOXGAQ-YCRREMRBSA-N

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.

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 Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H317,H334
• Precautionary Statements: P280 - P301 + P312 + P330 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves