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Merck

N7878

Sigma-Aldrich

Nitrofurantoin

98.0-102.0% (EP, UV)

Synonym(e):

N-(5-Nitro-2-furfuryliden)-1-aminohydantoin, Furadantin, Nitrofurantoin

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About This Item

Empirische Formel (Hill-System):
C8H6N4O5
CAS-Nummer:
Molekulargewicht:
238.16
Beilstein:
893207
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
51102829
PubChem Substanz-ID:
NACRES:
NA.85

Qualitätsniveau

Assay

98.0-102.0% (EP, UV)

Form

(Crystalline Powder or crystals)

Farbe

yellow

Löslichkeit

DMF: soluble 50 mg/mL

Wirkungsspektrum von Antibiotika

Gram-negative bacteria
Gram-positive bacteria

Wirkungsweise

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+

InChIKey

NXFQHRVNIOXGAQ-YCRREMRBSA-N

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Anwendung

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. Wirkung

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.

Sonstige Hinweise

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

Piktogramme

Health hazardExclamation mark

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

J Pourahmad et al.
Advances in experimental medicine and biology, 500, 261-265 (2002-01-05)
1. The enzymes responsible for the reductive activation of NFT are not known. We have now shown that under aerobic conditions, inhibitors of cytochrome P450 or P450 reductase but not DT diaphorase prevented NFT induced cytotoxicity and reactive oxygen species
W Shen et al.
Human & experimental toxicology, 15(5), 428-434 (1996-05-01)
1. Nitrofurantoin is an antimicrobial agent which produces hepatotoxicity caused by the redox cycling of the nitro group and its radical anion. This futile cycling triggers a complex series of events known collectively as oxidative stress. 2. Our goal was
C Michiels et al.
Biochimica et biophysica acta, 967(3), 341-347 (1988-12-15)
The toxicity of nitrofurantoin was studied on human WI-38 fibroblasts: this chemical was lethal when added at concentrations higher than 5.10(-5) M in the culture medium. The protection afforded by antioxidants was then tested: alpha-tocopherol gave at 10(-4) M a
Mutations to Nitrofurantoin and Nitrofurazone Resistance in Escherichia coli K12
Anthony S. Breeze and EMMANUEL E. OBASEIKI-EBOR
Microbiology, 129, 99-103 (1983)
Gitte M Knudsen et al.
Applied and environmental microbiology, 79(23), 7390-7397 (2013-09-24)
Listeria monocytogenes can cause the serious infection listeriosis, which despite antibiotic treatment has a high mortality. Understanding the response of L. monocytogenes to antibiotic exposure is therefore important to ensure treatment success. Some bacteria survive antibiotic treatment by formation of

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