5079. Ipronidazole

Nomenclature

CAS number: 14885-29-1
1-Methyl-2-(1-methylethyl)-5-nitro-1H-imidazole; 2-isopropyl-1-methyl-5-nitroimidazole; Ro-7-1554; Ipropran (Roche).
C7H11N3O2; mol wt 169.18.
C 49.70%, H 6.55%, N 24.84%, O 18.91%.

Description and references

Prepn: GB 1119636; M. Hoffer, M. Mitrovic, US 3634446 (1968, 1972 both to Hoffmann-La Roche); K. Butler, ZA 6607466 (1968 to Pfizer), C.A. 71, 3384e (1969). Structure-activity relationship: K. Butler et al., J. Med. Chem. 10, 891 (1967). Activity studies as an antihistomonal agent: M. Mitrovic et al., Antimicrob. Agents Chemother. 1968, 445; M. Mitrovic, E. G. Schildknecht, Poult. Sci. 49, 86 (1970); as a growth promotant: W. L. Marusich et al., ibid. 98. Toxicity studies: eidem, ibid. 92.

Chemical structure

Properties

White plates, mp 60°. LD50 orally in poults: 640 ± 25 mg/kg (Marusich, p 92).

Derivative

Hydrochloride.

Properties

mp 177-182°. Water-soluble.

Therapeutic Category (Veterinary)

Antiprotozoal (Histomonas).