Iodixanol Chemical Properties

Melting point:

262-267°C (dec.)

Boiling point:

1250.9±65.0 °C(Predicted)

Density 

1.266 ±0.003

vapor pressure 

0Pa at 20℃

refractive index 

n 1.4128 ±0.0003

storage temp. 

Refrigerator

solubility 

Freely soluble in water, sparingly soluble in methanol, practically insoluble in methylene chloride.

pka

11.04±0.46(Predicted)

color 

White

LogP

0.7

EPA Substance Registry System

1,3-Benzenedicarboxamide, 5,5'-[(2-hydroxy-1,3-propanediyl)bis(acetylimino)]bis[N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo- (92339-11-2)

Safety Information

HS Code 

2924296000

Hazardous Substances Data

92339-11-2(Hazardous Substances Data)

Toxicity

LD50 i.v. in mice: 21 gI/kg (Palmers)

MSDS

• Language:English Provider:Iodixanol

Iodixanol Usage And Synthesis

Chemical Properties

White Solid

Originator

OptiPrep,Nycomed Pharma,Norway

Uses

Nonionic, dimeric x-ray contrast medium. Diagnostic aid (radiopaque medium).

Definition

ChEBI: A dimeric, non-ionic, water-soluble, radiographic contrast agent, used particularly in coronary angiography.

Manufacturing Process

Dimethyl 5-nitroisophthalate (215 g) and 1-amino-2,3-propandiol (196 g)were refluxed in methanol (500 ml). After twenty hours the solution was cooled and stored in a refrigerator overnight. The product 5-nitro-N,N'- bis(2,3-dihydroxypropyl)-isophthalamide was filtered and washed with methanol. Yield: 270 g (84%). M.p. 128-132°C.
5-Nitro-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide (18.1 g) was suspended in water (250 ml), conc. hydrochloric acid (4.2 ml) and 10% PdO/charcoal (0.5 g) were added, and the mixture hydrogenated in a Parr apparatus for one day. After filtration the filtrate was heated at 80-90°C and 3.88 M NaICl2 (42.5 ml) was added through a dropping funnel over 1 hour. The solution was heated for 2.5 hours. After cooling to 20°C 5-amino-2,4,6-triiodo-N,N'- bis(2,3-dihydroxypropyl)-isophthalamide crystallized out.
5-Amino-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide (110 g) was suspended in acetic anhydride (480 ml) and heated to 50°C. Concentrated sulfuric acid (3 ml) was then added. The starting material was dissolved after a few minutes, and the reaction mixture was heated at 60°C for 75 min. After cooling the residue dissolved in methanol (300 ml) with water (150 ml) the solution was heated to 50°C and the pH adjusted to about 10.5 by 10 N sodium hydroxide. After 4-5 hours the pH didn't decrease, and the hydrolysis was complete. The reaction mixture was cooled to 20°C and neutralized by adding hydrochloric acid. After stirring overnight 5-Acetamido- 2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide was filtered and washed with water. Yield: 94 g (80%). Melting point 275°C, dec.
2-Methoxyethanol (300 ml) and sodium hydroxide (20 g) was added to the reactor at 50°C, and 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6- triiodoisophtalamide (304 g) was added after two hours of stirring. All solids were allowed to dissolve overnight before cooling to 30°C and adjustment to pH 12 with diluted hydrochloric acid. Epichlorohydrin (11 g) was added to the solution after further cooling to 15°C, and the reaction was allowed to proceed for 51 hours. As a result 1,3-bis(acetamido)-N,N'-bis[3,5-bis(2,3- dihydroxypropylaminocarbonyl)-2,4,6-triiodophenyl]-2-hydroxypropane was obtained.

brand name

Visipaque (GE Healthcare).

Therapeutic Function

Diagnostic aid

General Description

Iodixanol is a viscous, isosmolar,nonionic, water-soluble dimer with 49% iodine content.It is formulated as an isotonic solution for intravascular injectionand indicated for excretory urography, angiography,and CT procedures.

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