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Kluczowe dokumenty
N7878
Nitrofurantoin
98.0-102.0% (EP, UV)
Synonim(y):
N-(5-Nitro-2-furfurylidene)-1-aminohydantoin, Furadoxyl, Nitrofurantoine
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About This Item
Wzór empiryczny (zapis Hilla):
C8H6N4O5
Numer CAS:
Masa cząsteczkowa:
238.16
Beilstein:
893207
Numer WE:
Numer MDL:
Kod UNSPSC:
51102829
Identyfikator substancji w PubChem:
NACRES:
NA.85
Polecane produkty
Poziom jakości
Próba
98.0-102.0% (EP, UV)
Formularz
(Crystalline Powder or crystals)
kolor
yellow
rozpuszczalność
DMF: soluble 50 mg/mL
spektrum działania antybiotyku
Gram-negative bacteria
Gram-positive bacteria
Tryb działania
DNA synthesis | interferes
cell wall synthesis | interferes
protein synthesis | interferes
ciąg SMILES
[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+
Klucz InChI
NXFQHRVNIOXGAQ-YCRREMRBSA-N
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Zastosowanie
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.
Działania biochem./fizjol.
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.
Inne uwagi
Keep container tightly closed in a dry and well-ventilated place.Light sensitive.
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Hasło ostrzegawcze
Danger
Zwroty wskazujące rodzaj zagrożenia
Zwroty wskazujące środki ostrożności
Klasyfikacja zagrożeń
Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1
Kod klasy składowania
11 - Combustible Solids
Klasa zagrożenia wodnego (WGK)
WGK 1
Temperatura zapłonu (°F)
Not applicable
Temperatura zapłonu (°C)
Not applicable
Środki ochrony indywidualnej
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Klienci oglądali również te produkty
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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