14885-29-1

Off-White Solid

Ipropran,Roche,W. Germany,1981

An antihistomonal agent. Antiprotozoal (Histomonas).

Ipronidazole may be used as a reference standard in the determination of ipronidazole in tissue samples using high-performance liquid chromatography coupled with an ultraviolet detector (HPLC) and thermospray tandem mass spectrometry (HPLC-MS/MS).

ChEBI: Ipronidazole is a C-nitro compound and a member of imidazoles.

2-Isopropyl-4 (or 5-nitroimidazole) (31 g = 0.2 mol), dioxane (70 g) and dimethylsulfate (28 g = 0.22 mol) were heated on a steam bath under reflux for 45 minutes. The solvent was removed in vacuo on a steam bath, the residue dissolved in 20 ml of water and the product precipitated by the gradual addition of 80 g of 25% sodium hydroxide solution at 0°C. A small additional amount was obtained by extraction of the mother liquor with methylene chloride. The product melted at 60°C.
The product was purified as follows. 60 g of product was dissolved in 3N aqueous hydrochloric acid, the solution was treated with charcoal and filtered. The filtrate was neutralized by the gradual addition of aqueous concentrated ammonia at 0°C to 5°C under stirring whereupon the product precipitated in white plates as the neutralization proceeded. The precipitate was filtered by suction, washed on the filter with 50 ml of ice cold water and dried at room temperature, MP 60°C.
The hydrochloride salt was formed by reacting the product, dissolved in isopropanol, with 25% ethanolic hydrochloric acid, whereupon the salt precipitated and was isolated. It has a melting point of 177°C to 182°C (dec). Similarly, the bisulfate salt was formed using 96% sulfuric acid. It has a MP of 151.5°C to 152.5°C.

Ipropran [Veterinary] (Hoffmann-LaRoche).

Antiprotozoal

Ipronidazole is a veterinary drug, which is widely used in controlling histomoniasis in turkeys.