Iopamidol

Chemical properties

White Crystalline Powder

Originator

Iopamiro,Bracco,Italy,1981

The Uses of Iopamidol

Iopamidol is an organic iodine compound and used as a nonionic radiocontrast medium. Diagnostic aid (radiopaque medium). Iopamidol blocks x-rays as they pass through the body, thereby allowing body structures not containing iodine to be visualized. The degree of opacity produced by iopamidol is directly proportional to the total amount of the iodinated contrast agent in the path of the x-rays. The visualization of body structures is dependent upon the distribution and elimination of iopamidol. (NCI05)

Background

Iopamidol is a contrast agent developed by Bracco with nonionic, low-osmolar properties.

What are the applications of Application

Iopamidol is a nonionic radiocontrast medium

Definition

ChEBI: Iopamidol is a benzenedicarboxamide compound having N-substituted carbamoyl groups at the 1- and 3-positions, iodo substituents at the 2-, 4- and 6-positions and a (2S)-2-hydroxypropanamido group at the 5-position. It has a role as a radioopaque medium, an environmental contaminant and a xenobiotic. It is a benzenedicarboxamide, an organoiodine compound and a pentol.

Manufacturing Process

400 g (0.72 mol) 5-amino-2,4,6-triiodo-isophthalic acid was added to 200 ml thionyl chloride, the mixture was stirred at a boil for 6 hours, and the resulting solution was evaporated. The residue was dissolved in anhydrous ethyl acetate, and the solution was again evaporated to dryness. The solid material was dissolved in 4,000 ml ethyl acetate, and the solution was stirred into an ice-cold solution of 500 g sodium chloride and 200 g sodium bicarbonate in 2.5 liters water. The organic phase was separated from the aqueous solution, washed with aqueous sodium solution, dried by contact with anhydrous calcium chloride, and evaporated to dryness.
The residue of 420 g 5-amino-2,4,6-triiodo-isophthalyl chloride (97.5% yield) had a melting point above 300°C when recrystallized from toluene.
300 g (0.503 mol) 5-amino-2,4,6-triiodo-isophthalyl chloride was dissolved in 1,200 ml dimethylacetamide, and 187 g (126 mol) DL-2-acetoxypropionyl chloride was added dropwise to the solution with agitation. The mixture was permitted to stand overnight at ambient temperature and was then evaporated in a vacuum to approximately 400 ml. The oily residue was stirred into ice water to precipitate 353 g crystalline DL-5-(α-acetoxypropionylamino)- 2,4,6-triiodo-isophthalyl chloride (98% yield) which was purified by suspension in warm chloroform free alcohol.
The purified intermediate melted at 210°C. 70.9 g (0.10 mol) of the intermediate was dissolved in 150 ml dimethylacetamide, and 15 g (0.08 mol) tributylamine was added. The mixture was heated to 50°C, and 56.6 g (0.62 mol) 1,3-dihydroxyisopropylamine (2-amino-1,3-propanediol) dissolved in 80 ml dimethylacetamide was added drop by drop. The reaction went to completion within a few hours, and the reaction mixture was evaporated to dryness in a vacuum. The oily residue was added to 350 ml methylene chloride with vigorous agitation, and the resulting precipitate was filtered off and purified by repeated suspension of warm methylene chloride.
Work-up of the reaction mixture yielded 56.5 g (73.5%) DL-5-α- hydroxypropionylamino-2,4,6-triiodo-isophthalic acid di-(1,3- dihydroxyisopropylamide) which was recrystallized from aqueous ethanol and melted with decomposition above 300°C.

brand name

Isovue (Bracco).

Therapeutic Function

Diagnostic aid (radiopaque medium)

General Description

Iopamidol is a low-osmolar, nonionicmonomer with 49% organically bound iodine. It is indicatedfor use in angiography, excretory urography, andnumerous CT procedures.

Side Effects

Arm, back, or jaw pain; blurred vision; chest pain or discomfort; chest tightness or heaviness; confusion; dizziness, faintness, or lightheadedness when getting up suddenly from a lying or sitting position; fast or irregular heartbeat; feeling of warmth; hives; lightheadedness, dizziness, or fainting; nausea; redness of the face, neck, arms, and occasionally, upper chest; slow or irregular heartbeat; sudden sweating; trouble breathing; unusual tiredness or weakness

Toxicology

Serious skin reactions , including Stevens-Johnson syndrome, toxic epidermal necrolysis, drug reaction with eosinophilia and systemic symptoms (DRESS), and acute generalized exanthematous pustulosis can occur with this medicine. Results from in vitro HEK293T cell-based assays indicate that iopamidol affects mitochondrial function Treatment with iopamidol induces ATP depletion, reduces the mitochondrial membrane potential, and elevates mitochondrial superoxide and reactive oxygen species accumulation.

Metabolism

Not Available

Mode of action

Iopamidol is a Radiographic Contrast Agent. The mechanism of action of iopamidol is as a X-Ray Contrast Activity.