14885-29-1 Usage
Description
Ipronidazole, also known by the brand name Ipropran, is a veterinary drug that belongs to the class of nitroimidazoles. It is an off-white solid with potent antiprotozoal and antihistomonal properties, making it a valuable compound in the treatment and control of specific parasitic infections in animals.
Uses
Used in Veterinary Medicine:
Ipronidazole is used as an antiprotozoal agent for the control and treatment of histomoniasis in turkeys. Histomoniasis, also known as blackhead disease, is a parasitic infection caused by the protozoan Histomonas meleagridis, which can lead to significant economic losses in the poultry industry. Ipronidazole effectively targets and eliminates the parasite, reducing the prevalence and severity of the disease in affected flocks.
Used in Analytical Chemistry:
Ipronidazole is also utilized as a reference standard in the determination of its concentration in tissue samples. High-performance liquid chromatography (HPLC) coupled with an ultraviolet detector and thermospray tandem mass spectrometry (HPLC-MS/MS) are employed to accurately measure and analyze ipronidazole levels. This application is crucial for ensuring the proper dosage and efficacy of the drug in veterinary medicine, as well as for monitoring its presence and potential residues in animal products for food safety purposes.
Originator
Ipropran,Roche,W. Germany,1981
Manufacturing Process
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.
Therapeutic Function
Antiprotozoal
Check Digit Verification of cas no
The CAS Registry Mumber 14885-29-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,8,8 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 14885-29:
(7*1)+(6*4)+(5*8)+(4*8)+(3*5)+(2*2)+(1*9)=131
131 % 10 = 1
So 14885-29-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H11N3O2/c1-5(2)7-8-4-6(9(7)3)10(11)12/h4-5H,1-3H3
14885-29-1Relevant articles and documents
Crystal and molecular structure of imidazole derivatives with different substituents
Devarajegowda,Prasad, J. Shashidhara,Sridhar,Abdoh
, p. 317 - 330 (2007/10/03)
The crystal and molecular structures of 1-Methyl-2-Isopropyl-5-Nitroimidazole (A) and 1-Methyl-2(Thiophenyl)-Methyl-5-Nitroimidazole (B) derivatives were determined by X-ray diffraction methods. The compound A, C7H11N3O2, crystallises in the monoclinic space group P21/c with a = 9.9582(2) angstrom, b = 6.5240(4) angstrom, c = 13.5560(3) angstrom, β = 99.8930(17)°, V = 867.6(5) angstrom3, Z = 4, Dcalc = 1.295 Mg/m3, μ = 0.813 mm-1, F000 = 360, CuKα = 1.5406 angstrom and R = 0.09. The five membered ring with two nitrogen atoms is planar. Layering is observed down a and b axes. The compound B, C11H11N3O2S, crystallises in the triclinic space group P1 with a = 6.270(10) angstrom, b = 27.874(12) angstrom, c = 12.960(3) angstrom, α = 90°, β = 89.90°, γ = 90°, V = 2266(35) angstrom3, Z = 8, Dcalc = 1.461 Mg/m3, μ = 2.504 mm-1, F000 = 1040, CuKα = 1.5406 angstrom and R = 0.11.
Production of 1-alkyl-5-nitroimidazoles
-
, (2008/06/13)
1-Alkyl-5-nitroimidazoles are prepared by reacting a 5-nitroimidazole with an alkylating agent in the presence of an aliphatic carboxylic acid. The products are intermediates for the production of dyes, textiles auxiliaries and insecticides.
