Iopamidol CAS 60166-93-0
Introduction：Basic information about Iopamidol CAS 60166-93-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Iopamidol Basic information
| Product Name: | Iopamidol |
| Synonyms: | N,N'-Bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydroxy-1-oxopropyl)amino)-2,4,6-triiodo-1,3-Benzenedicarboxamide;N,N'-BIS(1,3-DIHYDROXYPROPAN-2-YL)-5-(2-HYDROXYPROPANOYLAMINO)-2,4,6-TRIIODO-BENZENE-1,3-DICARBOXAMIDE;1,3-benzenedicarboxamide,n,n’-bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydr;-2-propylamide);6-triiodo-(s)-oxy-1-oxopropyl)amino)-;b-15000;hthalamide;iopamiro |
| CAS: | 60166-93-0 |
| MF: | C17H22I3N3O8 |
| MW: | 777.09 |
| EINECS: | 262-093-6 |
| Product Categories: | Diagnostic;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 60166-93-0.mol |
Iopamidol Chemical Properties
| Melting point | >3200C (dec) |
| alpha | D20 -2.01° (c = 10 in water) |
| Boiling point | 740.14°C (rough estimate) |
| density | 2.0203 (estimate) |
| storage temp. | Keep in dark place,Sealed in dry,2-8°C |
| solubility | Freely soluble in water, very slightly soluble in methanol, practically insoluble in ethanol (96 per cent) and in methylene chloride |
| pka | pKa (25°) 10.70 |
| form | Solid |
| color | White to off-white |
| Water Solubility | 473.7g/L(25 ºC) |
| Major Application | pharmaceutical (small molecule) |
| InChIKey | XQZXYNRDCRIARQ-LURJTMIESA-N |
| SMILES | C1(C(NC(CO)CO)=O)=C(I)C(NC(=O)[C@@H](O)C)=C(I)C(C(NC(CO)CO)=O)=C1I |
| CAS DataBase Reference | 60166-93-0(CAS DataBase Reference) |
Safety Information
| WGK Germany | WGK 1 |
| HS Code | 2924296000 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 60166-93-0(Hazardous Substances Data) |
| Toxicity | LD50 in mice, rats, rabbits, dogs (g/kg): 44.5, 28.2, 19.6, 34.7 i.v. (Felder); LD50 in mice (mg iodine/kg body wt): 21,800 i.v.; 20,000 i.p.; 1500 intracerebral (Felder, Pitre). |
| 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 mlthionyl chloride, the mixture was stirred at a boil for 6 hours, and theresulting solution was evaporated. The residue was dissolved in anhydrousethyl acetate, and the solution was again evaporated to dryness. The solidmaterial was dissolved in 4,000 ml ethyl acetate, and the solution was stirredinto an ice-cold solution of 500 g sodium chloride and 200 g sodiumbicarbonate in 2.5 liters water. The organic phase was separated from theaqueous solution, washed with aqueous sodium solution, dried by contact withanhydrous 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 in1,200 ml dimethylacetamide, and 187 g (126 mol) DL-2-acetoxypropionylchloride was added dropwise to the solution with agitation. The mixture waspermitted to stand overnight at ambient temperature and was thenevaporated in a vacuum to approximately 400 ml. The oily residue was stirredinto ice water to precipitate 353 g crystalline DL-5-(α-acetoxypropionylamino)-2,4,6-triiodo-isophthalyl chloride (98% yield) which was purified bysuspension in warm chloroform free alcohol. The purified intermediate melted at 210°C. 70.9 g (0.10 mol) of theintermediate 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 (0.62mol) 1,3-dihydroxyisopropylamine (2-amino-1,3-propanediol) dissolved in 80ml dimethylacetamide was added drop by drop. The reaction went tocompletion within a few hours, and the reaction mixture was evaporated todryness in a vacuum. The oily residue was added to 350 ml methylenechloride with vigorous agitation, and the resulting precipitate was filtered offand 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 andmelted 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. |
| Mode of action | Iopamidol is a Radiographic Contrast Agent. The mechanism of action of iopamidol is as a X-Ray Contrast Activity. |
| References | [1] Patent: EP883597, 2005, B1. Location in patent: Page/Page column 6-7 [2] Patent: US6350908, 2002, B1. Location in patent: Example 1 |
Iopamidol Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->1,3-Propanediol, 2-(2,2-diethoxyethyl)-,monoacetate,(R)--->2-Amino-1,3,4-thiadiazole-->5-Amino-2,4,6-triiodoisophthalic acid-->5-amino-N1,N3-bis(1,3-dihydroxypropan-2-yl)isophthalamide-->5-Amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl) ethyl]-2,4,6-triiodobenzene-1,3-dicarboxamide-->(S)-5-[2-(acetyloxy)propanamido]-2,4,6-triiodo-1,3-di(chloroformyl)benzene-->2-Amino-1,3-propanediol-->5-Nitroisophthalic acid |
