1-[(E)-[(2E)-3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino]imidazolidine-2,4-dione

• ChemBase ID: 169502
• Molecular Formular: C10H8N4O5
• Molecular Mass: 264.19432
• Monoisotopic Mass: 264.04946938
• SMILES: c1(/C=C/C=N/N2C(=O)NC(=O)C2)oc(cc1)[N+](=O)[O-]
• Canonical SMILES: O=C1NC(=O)N(C1)/N=C/C=C/c1ccc(o1)[N+](=O)[O-]
• InChI: InChI=1S/C10H8N4O5/c15-8-6-13(10(16)12-8)11-5-1-2-7-3-4-9(19-7)14(17)18/h1-5H,6H2,(H,12,15,16)/b2-1+,11-5+
• InChIKey: DECBQELQORZLLP-UAIOPKHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(E)-[(2E)-3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino]imidazolidine-2,4-dione
• IUPAC Traditional name: 1-[(E)-[(2E)-3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino]imidazolidine-2,4-dione
• Synonyms: 1-[[3-(5-Nitro-2-furanyl)-2-propen-1-ylidene]amino]-2,4-imidazolidinedione; 1-[3-(5-Nitro-2-furyl)allylidenamino]hydantoin; Akritoin; F 35; Furazidin; Furazidine; NF 416; Furagin

Database IDs

• CAS Number: 1672-88-4
• PubChem SID: 162263634
• PubChem CID: 6870646

CALCULATED PROPERTIES

• Acid pKa: 9.233764
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.07018938
• LogD (pH = 7.4): 0.06402241
• Log P: 0.07027186
• Molar Refractivity: 62.6066 cm^3
• Polarizability: 22.652895 Å^3
• Polar Surface Area: 120.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 267-270°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F863000

Furagin (a nitrofurantoin analog) has the same efficacy in treating acute cystitis as Ciprofloxacin, however the duration of therapy is longer. Antibacterial.

REFERENCES

• Agace, W., et al.: J. Clin. Invest., 92, 780 (1993)
• Lawrenson, R., et al.: J. Antimicrob. Chemother., 48, 895 (1993)
• Dalhoff, A., et al.: Lancet Infect. Dis., 3, 359 (1993)
• Thumbikat, P., et al.: J. Immunol., 176, 3080 (1993)