F9505

Furazolidone

• Synonym(s): 3-(5-Nitrofurfurylideneamino)-2-oxazolidinone
• Empirical Formula (Hill Notation): C₈H₇N₃O₅
• CAS Number: 67-45-8
• Molecular Weight: 225.16
• Beilstein: 8317414
• EC Number: 200-653-3
• MDL number: MFCD00010550
• UNSPSC Code: 51102829
• PubChem Substance ID: 24894997
• NACRES: NA.85

Properties

• biological source: synthetic
• form: powder
• color: yellow
• mp: 256-256 °C
• solubility: formic acid: 50 mg/mL
• antibiotic activity spectrum: Gram-positive bacteria; parasites
• Mode of action: enzyme | inhibits
• SMILES string: [O-][N+](=O)c1ccc(\C=N\N2CCOC2=O)o1
• InChI: 1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2/b9-5+
• InChI key: PLHJDBGFXBMTGZ-WEVVVXLNSA-N

Description

Application

Furazolidone is a nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone binds bacterial DNA, which leads to the gradual inhibition of monoamine oxidase. It is used to treat anorexia and antagonism of thiamin utilization in poultry. Furazolidone increases thapsigargin-sensitive Ca²⁺-ATPase in chick cardiac myocytes.

Biochem/physiol Actions

Furazolidone and its generated free radicals, may bind to DNA and induce cross-links. Bacterial DNA is particularly susceptible to this drug, which results in high levels of mutations (transitions and transversions) in the bacterial chromosome. Its mechanism of action minimizes the development of resistant organisms. Furazolidone is a monoamine oxidase (MAO) inhibitor and is used as a DNA interstrand cross-linking agent.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H361fd
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves