73334-05-1

Basic information

• Product Name: 2-(2-methyl-5-nitro-imidazol-1-yl)ethoxyphosphonic acid
• Synonyms: 2-(2-methyl-5-nitro-imidazol-1-yl)ethoxyphosphonic acid;2-Methyl-5-nitro-1H-imidazole-1-ethanol phosphoric acid;Metronidazole phosphate;Metronidazole Phosphoester;Phosphoric acid dihydrogen 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester;U-54555
• CAS NO: 73334-05-1
• Molecular Formula: C₆H₁₀N₃O₆P
• Molecular Weight: 0
• Mol File: 73334-05-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 560.9°C at 760 mmHg
• Flash Point: 293°C
• Appearance: /
• Density: 1.79g/cm³
• Vapor Pressure: 2.04E-13mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-(2-methyl-5-nitro-imidazol-1-yl)ethoxyphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-methyl-5-nitro-imidazol-1-yl)ethoxyphosphonic acid(73334-05-1)
• EPA Substance Registry System: 2-(2-methyl-5-nitro-imidazol-1-yl)ethoxyphosphonic acid(73334-05-1)

Safety Data

• Hazardous Substances Data: 73334-05-1(Hazardous Substances Data)

Usage

Uses

Antibacterial; antiprotozoal.

InChI:InChI=1/C6H10N3O6P/c1-5-7-4-6(9(10)11)8(5)2-3-15-16(12,13)14/h4H,2-3H2,1H3,(H2,12,13,14)

Upstream product

• 443-48-1 metronidazole 

Downstream Products

• 443-48-1 metronidazole 

Relevant articles and documents

Metronidazole phosphate - A water-soluble prodrug for parenteral solutions of metronidazole

To develop a parenteral solution of relatively water-insoluble metronidazole (2-methyl-5-nitro-1H-imidazole-1-ethanol), its phosphate ester was synthesized via two routes. One route utilized 2-cyanoethyl phosphate and the other utilized pyrophosphoryl tetrachloride. The first method used dicyclohexylcarbodiimide as a coupling agent and the cyamoethyl group was removed under mild alkaline conditions. The second method was a one-step procedure in which free acid of metronidazole phosphate was isolated as a crystalline solid. The solubility of metronidazole in various solvents was determined at 25°. From the pH-dependence of its aqueous solubility, the pKa of the conjugate acid of metronidazole was estimated to be 2.62, which agreed well with the pKa values of other nitroimidazoles. Metronidazole phosphate behaved as a zwitterionic compound in an acidic medium with a minimum solubility at pH 2.0. At pH 7, its solubility was ~50 times that of metronidazole. The phosphate ester was so soluble at pH higher than 7 that it was difficult to measure the solubility accurately. In human serum, the hydrolysis of metronidazole phosphate followed zero-order kinetics at an initial concentration of 0.25 mg/ml or higher, presumably due to enzyme saturation (0.035 mg/ml/hr at 37°). A reversed-phase HPLC procedure was adopted to monitor the appearance of metronidazole and the disappearance of metronidazole phosphate. Subcutaneous administration of metronidazole phosphate to rats produced a blood level of bioactivity comparable to that observed after administration of metronidazole.