Nitrofurantoin

Empirical Formula (Hill Notation):	C8H6N4O5
CAS Number:	67-20-9
Molecular Weight:	238.16
Beilstein/REAXYS Number:	893207
EC Number:	200-646-5
MDL number:	MFCD00003224
PubChem Substance ID:	24897842
NACRES:	NA.85

Кат. номер

N7878-250G

N7878-25G

N7878-10G

N7878-100G

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.
10, 25, 100, 250 g in glass bottle
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.
Keep container tightly closed in a dry and well-ventilated place.Light sensitive.

Quality Level	200,
assay	98.0-102.0% (EP, UV)
form	(Crystalline Powder or crystals)
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
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

pictograms	GHS07,GHS08
signalword	Danger
hcodes	H302 - H317 - H334
pcodes	P280 - P301 + P312 + P330 - P302 + P352
Personal Protective Equipment	dust mask type N95 (US),, Eyeshields,, Faceshields,, Gloves,
RIDADR	NONH for all modes of transport
WGK Germany	WGK 1
Flash Point F	Not applicable
Flash Point C	Not applicable