Nitrofurantoin
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| Category | Antibiotics |
| Catalog number | BBF-04623 |
| CAS | 67-20-9 |
| Molecular Weight | 238.16 |
| Molecular Formula | C8H6N4O5 |
| Purity | ≥98.0% |
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Description
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 treat urinary tract infections. It is active against both Gram-positive and Gram-negative bacteria.
Specification
| Related CAS | 17140-81-7 (monohydrate) 54-87-5 (hydrochloride) |
| Synonyms | N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; Furadoxyl; 1-(((5-nitro-2-furanyl)methylene)amino)-2,4-imidazolidinedione; 1-(5-Nitro-2-furfurylideneamino)hydantoin; 5-Nitrofurantoin; Berkfurin; Chemiofuran; Cyantin; Cystit; Furadantoin; Furadoine; Nifuranti |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Store at -20°C |
| IUPAC Name | 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione |
| Canonical SMILES | C1C(=O)NC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-] |
| InChI | 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 |
| Source | Synthetic |
Properties
| Appearance | Yellow Crystalline Powder or Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Melting Point | >213°C (dec.) |
| Density | 0.915 g/cm3 at 20°C |
| Solubility | Soluble in DMSO, Methanol |
| LogP | -0.47 |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced reactive intermediates that are thought to modulate and damage ribosomal proteins or other macromolecules, especially DNA, causing inhibition of DNA, RNA, protein, and cell wall synthesis. Nitrofurantoin inhibits bacterial acetyl-coenzyme A, interfering with the organism's carbohydrate metabolism. The drug also can disrupt bacterial cell wall formation. The overall effect is inhibition of bacterial growth or cell death. |
Reference Reading
1.Evaluation of the Risk of Nitrofurantoin Lung Injury and Its Efficacy in Diminished Kidney Function in Older Adults in a Large Integrated Healthcare System: A Matched Cohort Study.
Santos JM1, Batech M2, Pelter MA1, Deamer RL1. J Am Geriatr Soc. 2016 Apr;64(4):798-805. doi: 10.1111/jgs.14072.
OBJECTIVES: To determine the risk to older adults of lung injury associated with treatment of cystitis using nitrofurantoin and the risk of treatment failure in the presence of diminished creatinine clearance (CrCl).
2.Oxidative bioactivation of nitrofurantoin in rat liver microsomes.
Li H1, Lin D1, Peng Y1, Zheng J2,3. Xenobiotica. 2016 Apr 19:1-9. [Epub ahead of print]
1. Nitrofurantoin (NFT), a 5-nitrofuran derivative, has been widely used for the treatment of specific urinary tract infections. It has been reported that exposure to NFT was associated with various adverse effects, particularly hepatotoxicity and pneumotoxicity. The objective of the study was to identify reactive metabolites of NFT and explore the mechanisms of the toxicities. 2. An epoxide intermediate generated in microsomal incubations was trapped by glutathione (GSH) and 4-bromobenzyl mercaptan (BBM), and the resulting GSH and BBM conjugates were characterized by LC-MS/MS. A spontaneous denitration took place in the trapping reaction. 2-Nitrofuran and 2-hydroxyfuran as model compounds were employed to probe the mechanism of the denitration. 3. The oxidative activation of NFT was P450-dependent, and P450 3A5 and P450 2A6 were the principal enzymes responsible for the bioactivation. The findings facilitate the understanding of the mechanisms of NFT-induced toxicities.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6N4O5
Molecular Weight (Monoisotopic Mass): 238.0338 Da
Molecular Weight (Avergae Mass): 238.157 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6N4O5
Molecular Weight (Monoisotopic Mass): 238.0338 Da
Molecular Weight (Avergae Mass): 238.157 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6N4O5
Molecular Weight (Monoisotopic Mass): 238.0338 Da
Molecular Weight (Avergae Mass): 238.157 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6N4O5
Molecular Weight (Monoisotopic Mass): 238.0338 Da
Molecular Weight (Avergae Mass): 238.157 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
