This product is soluble in dimethylformamide (DMF, 50 mg/mL), with heat as needed, yielding a clear, yellow/green solution. It is also soluble in water (0.19 mg/mL), ethanol (0.51 mg/mL), acetone (5.1 mg/mL), glycerol (0.6 mg/mL), and polyethylene glycol (15 mg/mL). Nitrofurantoin is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, dissolve first in DMSO and then dilute with the buffer of choice. It has a solubility of ~0.5 mg/mL in a 1:2 solution of DMSO:PBS (pH 7.2) using this method. It is not recommended to store the aqueous solution for longer than a day.
N7878
Nitrofurantoin
98.0-102.0% (EP, UV), meets EP testing specifications
Synonym(s):
N-(5-Nitro-2-furfurylidene)-1-aminohydantoin, Furadoxyl, Nitrofurantoine
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About This Item
Empirical Formula (Hill Notation):
C8H6N4O5
CAS Number:
Molecular Weight:
238.16
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
EC Number:
200-646-5
Beilstein/REAXYS Number:
893207
MDL number:
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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
Quality Level
agency
meets EP testing specifications
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 bacteria, Gram-positive bacteria
mode of action
DNA synthesis | interferes, cell wall synthesis | interferes, protein synthesis | interferes
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1 of 4
This Item | 46502 | PHR1191 | S6256 |
|---|---|---|---|
| mode of action DNA synthesis | interferes, protein synthesis | interferes, cell wall synthesis | interferes | mode of action DNA synthesis | interferes, cell wall synthesis | interferes, protein synthesis | interferes | mode of action - | mode of action DNA synthesis | interferes, enzyme | inhibits |
| antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum - | antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria |
| Quality Level 200 | Quality Level 200 | Quality Level 300 | Quality Level 200 |
| form (Crystalline Powder or crystals) | form - | form - | form powder or crystals |
| assay 98.0-102.0% (EP, UV) | assay - | assay - | assay 99.0-101.0% (on dried basis) |
| solubility DMF: soluble 50 mg/mL | solubility - | solubility - | solubility - |
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Mutations to Nitrofurantoin and Nitrofurazone Resistance in Escherichia coli K12
Anthony S. Breeze and EMMANUEL E. OBASEIKI-EBOR
Microbiology, 129, 99-103 (1983)
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
Martindale: The Extra Pharmacopoeia
Martindale: The Extra Pharmacopoeia, 1529-1531 (1996)
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
S C Nickerson et al.
American journal of veterinary research, 46(11), 2259-2265 (1985-11-01)
Effects of antibiotics and antibiotic vehicles on polymorphonuclear leukocytes (PMNL) isolated from bovine mammary glands were studied in vitro. Amikacin, dicloxacillin, erythromycin, gentamicin, lincomycin, nitrofurantoin, novobiocin-penicillin, polymyxin B, rifampin, tetracycline, or tiamulin was added to culture medium at 1 mg/ml
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Product Information Sheet
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I purchased Nitrofurantoin (N7878). It dissolves in DMSO, but precipitates immediately when water or medium is added, even below 1–3% DMSO. What is the recommended solvent and how can I prepare a stable stock solution?”
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How can I determine the shelf life / expiration / retest date of this product?
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If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdfHelpful?
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How is shipping temperature determined? And how is it related to the product storage temperature?
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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