6599. Nitrofurantoin

Nomenclature

CAS number: 67-20-9
1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; N-(5-nitro-2-furfurylidene)-1-aminohydantoin; 1-(5-nitro-2-furfurylideneamino)hydantoin; Berkfurin (Berk); Chemiofuran (Italfarmaco); Cyantin (Lederle); Cystit (BMS); Fua-Med (Med. Fabrik); Furachel (Rachelle); Furalan (Lannett); Furadantin (Dura Pharm.); Furadantine MC (Procter & Gamble); Furadoin (Eaton); Furantoina (Uriach); Furobactina (Esteve); Furophen T-Caps (Krewel); Ituran (Promonta); Macrodantin (Eaton); Parfuran (Parke-Davis); Trantoin (McKesson); Urantoin (DDSA); Urizept (RPR); Urodin (Streuli); Urolong (Thiemann); Uro-Tablinen (Sanorania); Welfurin (GAP).
C8H6N4O5; mol wt 238.16.
C 40.34%, H 2.54%, N 23.52%, O 33.59%.

Description and references

Prepn from 1-aminohydantoin sulfate and 5-nitro-2-furaldehyde diacetate: K. J. Hayes, US 2610181 (1952 to Eaton Labs.); Swirska et al., Przem. Chem. 11 (34), 306 (1955), C.A. 52, 14079b (1958). Alternate routes: J. G. Michels, US 2898335; G. Gever, C. J. O'Keefe, US 2927110 (1959, 1960 both to Norwich Pharmacal). LC-MS/MS determn of residues in meat: P. Mottier et al., J. Chromatogr. A 1067, 85 (2005). Clinical trial in urinary tract infection: R. G. Rogers et al., Am. J. Obstet. Gynecol. 191, 182 (2004). Comprehensive description: D. E. Cadwallader, H. W. Jun, Anal. Profiles Drug Subs. 5, 345-373 (1976).

Chemical structure

Properties

Orange-yellow needles from dil acetic acid, dec 270-272°. pKa 7.2. uv max: 370 nm (E1%1cm 776). Soly (mg/100 ml): water (pH 7) 19.0; 95% ethanol 51.0; acetone 510; DMF 8000; peanut oil 2.1; glycerol 60; polyethylene glycol 1500.

Derivative

Monohydrate.

Nomenclature

CAS number: 17140-81-7
Macrobid (Procter & Gamble).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Nitrofurans