6872. Ornidazole

Nomenclature

CAS number: 16773-42-5
α-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol; 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole; Ro-7-0207; Madelen (Finadiet); Ornidal (Selvi); Tiberal (Roche).
C7H10ClN3O3; mol wt 219.63.
C 38.28%, H 4.59%, Cl 16.14%, N 19.13%, O 21.85%.

Description and references

Prepn: NL 6606853; M. Hoffer, US 3435049 and US 3493582 (1966, 1969 and 1970, all to Hoffmann-La Roche). Activity studies: E. Grunberg et al., Proc. Soc. Exp. Biol. Med. 133, 490 (1970). Synthesis and antiprotozoal activity: M. Hoffer, E. Grunberg, J. Med. Chem. 17, 1019 (1974). Pharmacokinetics: D. E. Schwartz, F. Jeunet, Chemotherapy 22, 19 (1976).

Chemical structure

Properties

Crystals from toluene, mp 77-78°. uv max (2-propanol): 288, 312 nm (ε 3720, 9150). pKa: 2.4 ± 0.1. LD50 in rats, mice (mg/kg): 1780, 1420 orally (Grunberg). Also reported as LD50 in mice (mg/kg): >2000 orally, >2000 i.p. (Hoffer, Grunberg).

Therapeutic Category

Anti-infective.

Keywords

Antiseptic/Disinfectant