N7878

Nitrofurantoin

98.0-102.0% (EP, UV)

Manufacturer: Sigma Aldrich

CAS Number: 67-20-9

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

Select a Size

Pack Size SKU Availability Price
10 G N7878-10-G In Stock ₹ 4,070.20
25 G N7878-25-G In Stock ₹ 4,167.63
100 G N7878-100-G In Stock ₹ 14,722.00

N7878 - 10 G

₹ 4,070.20

In Stock

Quantity

1

Base Price: ₹ 4,070.20

GST (18%): ₹ 732.636

Total Price: ₹ 4,802.836

Quality Level

200

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 bacteriaGram-positive bacteria

Mode of action

DNA synthesis | interferescell wall synthesis | interferesprotein 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

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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[1] and antibiotic resistance[2].Nitrofurantoin is suitable for killing L. monocytogenes-persisters in vitro.[3] Studies has described the use of antioxidants to mitigate the toxic effects of nitrofurantoin on human WI-38 fibroblasts in culture.[4] 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.[5]
  • 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.[6] 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[7]. 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[1].
  • 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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves