6539. Nifurtoinol

Nomenclature

CAS number: 1088-92-2
3-(Hydroxymethyl)-1-[[(5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; 3-(hydroxymethyl)-1-[(5-nitrofurfurylidene)amino]hydantoin; 1-[(5-nitrofurfurylidene)amino]-3-(hydroxymethyl)hydantoin; Urfadyn (Zambon).
C9H8N4O6; mol wt 268.18.
C 40.31%, H 3.01%, N 20.89%, O 35.80%.

Description and references

Prepn: Michels, BE 611941 corresp to US 3446802 (1962, 1969 to Norwich Pharmacal); Spencer, Michels, J. Org. Chem. 29, 3416 (1964).

Chemical structure

Properties

Yellow crystals from aq formaldehyde. When heated on a melting-point block, loses formaldehyde, then further decomposes at same temp as nitrofurantoin. uv max (2% in dimethylformamide): 367.5, 265 nm (ε 17900, 12800).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Nitrofurans