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Nitrofurantoin

Catalog No. N7878 Name Sigma Aldrich
CAS Number 67-20-9 Website http://www.sigmaaldrich.com
M. F. C8H6N4O5 Telephone 1-800-521-8956
M. W. 238.15704 Fax
Purity Email
Storage Chembase ID: 104426

SYNONYMS

Title
呋喃妥因
IUPAC name
1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
IUPAC Traditional name
nitrofurantoin sodium
Synonyms
硝基呋喃妥因
呋喃坦啶
N-(5-硝基-2-呋喃亚甲基)-1-氨基海因

DATABASE IDS

MDL Number MFCD00003224
CAS Number 67-20-9
PubChem SID 24897842
Beilstein Number 893207
EC Number 200-646-5

PROPERTIES

Apperance yellow crystalline
GHS Pictograms GHS07
GHS Pictograms GHS08
GHS Signal Word Danger
GHS Hazard statements H302-H317-H334
European Hazard Symbols Harmful Harmful (Xn)
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
GHS Precautionary statements P261-P280-P342 + P311
Risk Statements 22-42/43
RTECS MU2800000
Safety Statements 22-36/37-45
German water hazard class 3

DETAILS

Description (English)
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 antiobiotic resistance2.
Biochem/physiol Actions
Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced 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 death3. 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 2O 2. 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 stress1.

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