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ChemicalBook >> CAS DataBase List >>Iopamidol

Iopamidol

CAS No.
60166-93-0
Chemical Name:
Iopamidol
Synonyms
isovue;niopam;b-15000;lamide);sq13396;Iopanol;iopamiro;Jopamiro;Solutras;iopamido
CBNumber:
CB5384796
Molecular Formula:
C17H22I3N3O8
Molecular Weight:
777.09
MDL Number:
MFCD00867931
MOL File:
60166-93-0.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-16 07:06:08
Product description Number Pack Size Price
Iopamidol European Pharmacopoeia (EP) Reference Standard I0329000 50 mg $175
Iopamidol 1344702 200mg $455
Iopamidol European Pharmacopoeia (EP) Reference Standard I0329000 i0329000 $153
Iopamidol I1011 5G $53
Iopamidol I1011 25G $184
More product size

Iopamidol 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
form Solid
pka pKa (25°) 10.70
color White to off-white
Water Solubility 473.7g/L(25 ºC)
Henry's Law Constant 9.0×1019 mol/(m3Pa) at 25℃, HSDB (2015)
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)
FDA UNII JR13W81H44
NCI Drug Dictionary Isovue
UNSPSC Code 41116107
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338
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).

Iopamidol price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I0329000 Iopamidol European Pharmacopoeia (EP) Reference Standard 60166-93-0 50 mg $175 2026-04-30 Buy
Sigma-Aldrich 1344702 Iopamidol 60166-93-0 200mg $455 2026-04-30 Buy
Sigma-Aldrich I0329000 Iopamidol European Pharmacopoeia (EP) Reference Standard 60166-93-0 i0329000 $153 2024-03-01 Buy
TCI Chemical I1011 Iopamidol 60166-93-0 5G $53 2026-04-30 Buy
TCI Chemical I1011 Iopamidol 60166-93-0 25G $184 2026-04-30 Buy
Product number Packaging Price Buy
I0329000 50 mg $175 Buy
1344702 200mg $455 Buy
I0329000 i0329000 $153 Buy
I1011 5G $53 Buy
I1011 25G $184 Buy

Iopamidol Chemical Properties,Uses,Production

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.

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

60166-91-8
534-03-2
60166-93-0
Synthesis of Iopamidol from (S)-5-[2-(acetyloxy)propanamido]-2,4,6-triiodo-1,3-di(chloroformyl)benzene and 2-Amino-1,3-propanediol
Global( 246)Suppliers
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Iopamidol Spectrum

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 iopamiron isovue isovue-370 jopamiron200 l-(+)-n,n’-bis(2-hydroxy-1-hydroxymethylethyl)-2,4,6-triiodo-5-lactamideisop l-5alpha-hydroxypropionylamino-2,4,6-triiodoisophthalicaciddi(1,3-dihydroxy l-5alpha-idrossipropionilamino-2,4,6-triiodoisoftal-di(1,3-diidrossi-2-propi lamide) niopam niopam300 solutrast solutrast370 sq13396 (S)-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodoisophthaldiamide Iomapidol Jopamiro N,NBis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxamide Solutras 1,3-Benzenedicarboxamide, N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-, (S)- 1,3-Benzenedicarboxamide, N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo- Iopamidol 300 Iopamiro 370 Iopamiron 300 Iopamiron 370 Isovue 300 (S)-N,N'-Bis(1,3-dihydroxypropan-2-yl)-5-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxamide Iopamidol (200 mg) (S)-N,N′-Bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-5-lactamidoisophthalamide Iopamidol ( for Contrast Agents ) IOPAMIRO;ISOVUE;IOPAMIRON;NIOPAM (2S)-Iopamidol, isomer mixture 1,3-Benzenedicarboxamide, N1,N3-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo- (S)-N1,N3-bis(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanamido)-2,4,6-triiodoisophthalamide Iopamidol USP/EP/BP iopamido (S)-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy... Iopamidol (1344702) Iopomidol Iopamidol IPAMIDOL (2S)-Iopamidol in methanol C14348400 Iopamidol Iopanol Iopamidol, 10 mM in DMSO Iopamidol,99% Iopamidol Material 60166-93-0 37438-68-8 77709 Diagnostic
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