12-06621. Nifuradene [Archived]

Nomenclature

CAS number: 555-84-0
1-[[(5-Nitro-2-furanyl)methylene]amino]-2-imidazolidinone; oxafuradene (rescinded); NF-246; NSC-6470; Renafur (Eaton).
C8H8N4O4; mol wt 224.17.
C 42.86%, H 3.60%, N 24.99%, O 28.55%.

Description and references

Prepn: Gever, Michels, US 2746960 (1956 to Norwich Pharm.); eidem, J. Am. Chem. Soc. 78, 5349 (1956); Michels, US 2776979 (1957 to Norwich Pharm.). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Chemical structure

Properties

Lemon-yellow solid from nitromethane, mp 261.5-263° (dec). Turns orange on standing, on washing with ethanol or on heating at 75-85°. uv max (water): 387.5, 273 nm (ε 17550, 13200). Soly in water: 88-109 mg/l. LD50 orally in rats: 1681 mg/kg (Goldenthal).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Nitrofurans

Status

This monograph has been retired and is no longer subject to revision or update.