Nitrofurantoin
SIGMA/N7878 - 98.0-102.0% (EP, UV)
Synonym: N-
CAS Number: 67-20-9
Empirical Formula (Hill Notation): C8H6N4O5
Molecular Weight: 238.16
EC Number: 200-646-5
MDL Number: MFCD00003224
Linear Formula: C8H6N4O5
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: N7878-250G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: N7878-100G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: N7878-25G
| antibiotic activity spectrum | Gram-negative bacteria |
| Gram-positive bacteria | |
| assay | 98.0-102.0% (EP, UV) |
| color | yellow |
| form | (Crystalline Powder or crystals) |
| InChI | 1S/C8H6N4O5/c13-6-4-11(8( |
| InChI key | NXFQHRVNIOXGAQ-YCRREMRBSA |
| mode of action | cell wall synthesis | interferes |
| DNA synthesis | interferes | |
| protein synthesis | interferes | |
| Quality Level | 200  |
| SMILES string | [O-][N+](=O)c1ccc(C=NN2 |
| solubility | DMF: soluble 50 mg/mL |
| 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. |
| Packaging: | 10, 25, 100, 250 g in glass bottle |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H302 - H317 - H334 |
| Precautionary statements | P280 - P301 + P312 + P330 - P302 + P352 |
| Hazard Codes | Xn |
| Risk Statements | 22-42/43 |
| Safety Statements | 22-36/37-45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 1 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | 98.0-102.0% (EP, UV) |
| UNSPSC | 51102829 |