3-methyl-4-[2-(5-nitrofuran-2-yl)diazen-1-yl]-1λ6-thiane-1,1-dione

• ChemBase ID: 154931
• Molecular Formular: C10H13N3O5S
• Molecular Mass: 287.29232
• Monoisotopic Mass: 287.05759153
• SMILES: CC1CS(=O)(=O)CCC1/N=N/c1ccc(o1)[N+](=O)[O-]
• Canonical SMILES: CC1CS(=O)(=O)CCC1/N=N/c1ccc(o1)[N+](=O)[O-]
• InChI: InChI=1S/C10H13N3O5S/c1-7-6-19(16,17)5-4-8(7)11-12-9-2-3-10(18-9)13(14)15/h2-3,7-8H,4-6H2,1H3
• InChIKey: FQPFGLOLUUUBIH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-4-[2-(5-nitrofuran-2-yl)diazen-1-yl]-1λ^6-thiane-1,1-dione
• IUPAC Traditional name: 3-methyl-4-[2-(5-nitrofuran-2-yl)diazen-1-yl]-1λ^6-thiane-1,1-dione
• Synonyms: (±)-Nifurtimox; (RS)-3-methyl-N-[(1E)-(5-nitro-2-furyl)methylene]thiomorpholin-4-amine 1,1-dioxide; 3-Methyl-4-(5′-nitrofurylidene-amino)-tetrahydro-4H-1,4-thiazine-1,1-dioxide; 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine 1,1-dioxide; BAY 2502; Thiomorpholine, 3-methyl-4-((5-nitrofurfurylidene)amino)-,1,1-dioxide; Nifurtimox

Database IDs

• CAS Number: 23256-30-6
• EC Number: 245-531-0
• PubChem SID: 162249069
• PubChem CID: 71312029

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.86543316
• LogD (pH = 7.4): 0.86546963
• Log P: 0.8654701
• Molar Refractivity: 67.1763 cm^3
• Polarizability: 25.498873 Å^3
• Polar Surface Area: 117.82 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥13 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C10H13N3O5S

DETAILS

Sigma Aldrich - N3415

Biochem/physiol Actions
Nifurtimox is a nitrofurane derivative used to treat diseases caused by trypanosomes. Nifurtimox was discovered empirically and its mechanism of action is unclear. It is believed that nifurtimox exerts its biological activity through the bioreduction of the nitro-group to a nitro-anion radical which undergoes redox-cycling with molecular oxygen.