1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione

• ChemBase ID: 104426
• Molecular Formular: C8H6N4O5
• Molecular Mass: 238.15704
• Monoisotopic Mass: 238.03381931
• SMILES: [O-][N+](=O)c1ccc(o1)/C=N/N1CC(=O)NC1=O
• Canonical SMILES: O=C1NC(=O)N(C1)/N=C/c1ccc(o1)[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)
• InChIKey: NXFQHRVNIOXGAQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione; 1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• IUPAC Traditional name: macrodantin; nitrofurantoin sodium; 1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• Synonyms: N-[5-Nitro-2-furfurylidene]-1-aminohydantoin; NITROFURANTOIN; Nitrofurantoin; N-(5-Nitro-2-furfurylidene)-1-aminohydantoin; Furadoxyl; Nitrofurantoine; 1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione; 1-((5-nitrofurfurylidene)amino)hydantoin; Furadantin; Macrodantin; Urantoin; 1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; 1-(5-Nitro-2-furfurylideneamino)hydantoin; 5-Nitrofurantoin; Berkfurin; Chemiofuran; Cyantin; Cystit; Furadantoin; Furadoin; Furadoine; Nifurantin; Nitoin; Nitrofurantoin; Novofuran; Orafuran; Urodin; Zoofurin; N-(5-硝基-2-呋喃亚甲基)-1-氨基海因; 呋喃坦啶; 硝基呋喃妥因; 呋喃妥因

Database IDs

• CAS Number: 67-20-9
• EC Number: 200-646-5
• MDL Number: MFCD00003224
• Beilstein Number: 893207
• PubChem SID: 24870238; 162091898; 24897842
• PubChem CID: 6604200

CALCULATED PROPERTIES

• Acid pKa: 8.2330885
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.22224307
• LogD (pH = 7.4): -0.28023475
• Log P: -0.22144999
• Molar Refractivity: 52.1099 cm^3
• Polarizability: 19.238554 Å^3
• Polar Surface Area: 118.05 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow crystalline
• Melting Point: 268°C

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• RTECS: MU2800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-42/43; R:22-40-60
• Safety Statements: 22-36/37-45; S:38-46-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Mechanism of Action: Damaging bacterial DNA, ribosomal proteins, DNA, effecting respiration, pyruvate metabolism and other macromolecules within the cell

Product Information

• Purity: 98%
• Grade: VETRANAL™, analytical standard
• Application(s): activity against: Escherichia coli; Enterococcus; Antibacterial agent used to treat urinary-tract infections and Staphylococcus aureus; Antiseptic; bactericidal at high-dose; some strains of Klebsiella; some strains of Enterobacter.; Staphylococcus saprophyticus
• Empirical Formula (Hill Notation): C8H6N4O5

DETAILS

MP Biomedicals - 02155881

(N-[5-Nitro-2-furfurylidene]-1-aminohydantoin) Yellow crystals.

Sigma Aldrich - N7878

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.

Sigma Aldrich - 46502

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - N493850

A nitrofuran antibiotic with low resistance potential that is rapidly metabolized by mammals. Active against both Gram-positive and Gram-negative bacteria. Nitrofurantoin is also a prooxidant that is cytotoxic due to the generation of intracellular H2O2.

REFERENCES

• Rogers, R.G., et al.: Am. J. Obstr. Gynecol., 191, 182 (1976)
• Cadwallader, D.E., et al.: Anal. Profiles Drug Subs., 5, 345 (1976)
• U.S. Pat., 1952, 2 610 181; CA, 47, 6980i, (synth)
• Swirska, A. et al., CA, 1958, 52, 14079, (synth)
• U.S. Pat., 1959, 2 898 335; CA, 54, 2356i, (synth)
• Cadwallader, D.E. et al., Anal. Profiles Drug Subst., 1976, 5, 345, (rev)
• Chamberlain, R.E., J. Antimicrob. Chemother., 1976, 2, 325, (pharmacol, rev)
• Bryan, G.T., Carcinog. - Compr. Surv., (Ed. Bryan, G.T.), Vol 4. Nitrofurans, Raven Press, N.Y., 1978, (book)
• Gleckman, R. et al., Am. J. Hosp. Pharm., 1979, 36, 342, (rev)
• Baeva, V. et al., CA, 1983, 98, 125968, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 824, (synonyms)
• IARC Monog., 1990, 50, 211, (rev, tox)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 187
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NGE000