60166-93-0 Usage
Chemical Properties
White Crystalline Powder
Originator
Iopamiro,Bracco,Italy,1981
Uses
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)
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.
Mode of action
Iopamidol is a Radiographic Contrast Agent. The mechanism of action of iopamidol is as a X-Ray Contrast Activity.
Check Digit Verification of cas no
The CAS Registry Mumber 60166-93-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,0,1,6 and 6 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 60166-93:
(7*6)+(6*0)+(5*1)+(4*6)+(3*6)+(2*9)+(1*3)=110
110 % 10 = 0
So 60166-93-0 is a valid CAS Registry Number.
60166-93-0Relevant articles and documents
PROCESS FOR THE PREPARATION OF IOPAMIDOL
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Paragraph 9-11, (2022/01/12)
The present invention provides a process for the preparation of a compound of Formula (II) wherein the process comprises: (i) reacting a compound of Formula (I) with pyridine and 2-acetyloxypropanoyl chloride (APC) to give a compound of Formula (II), wherein the compound of Formula (I) has the following structure.
PROCESS FOR THE PREPARATION OF IOPAMIDOL
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, (2015/05/26)
The present invention discloses a process for the preparation of Iopamidol of formula (II) and comprising the following steps: a) reacting the Compound (I) wherein X is OR2 or R3, and wherein R2 and R3 are a Ci-C6 linear or branched alkyl, C3-C6 cycloalkyl, C6 aryl, optionally substituted with a group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl and phenyl, with the acylating agent (S)-2-(acetyloxy)propanoyl chloride in a reaction medium to provide the acetyloxy derivative of Compound (I); b) hydrolyzing the intermediate from step a) with an aqueous solution at a pH comprised from 0 to 7, by adding water or a diluted alkaline solution such as sodium hydroxide or potassium hydroxide, freeing the hydroxyls from the boron-containing protective groups, obtaining the N-(S)-2-(acetyloxy)propanoyl derivative of Compound (II); c) alkaline hydrolysis to restore the (S)-2-(hydroxy)propanoyl group and to obtain lopamidol (II) and optional recovery of the boron derivative from the solution obtained in step b). The boron-containing protective group is versatile, efficient and recyclable. A one-pot synthesis, without intermediate isolation is provided, leading to a decreasing of recovered and recycled solvents and a significant increasing in the yield, representing a significant advantage in terms of cost-effectiveness of the entire process and environmental awareness.
Process For The Preparation Of Contrast Agents
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Paragraph 0063; 0064; 0070; 0071; 0072, (2013/06/04)
The present invention relates to a process for the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamidic derivatives comprising the Smiles rearrangement of a suitable precursor, by contact of an aqueous solution of this latter with an anion exchanger solid phase.
