Basic information
- CAS
78649-41-9- Standard SMILES
CN(C(=O)CO)c1c(I)c(C(=O)NCC(O)CO)c(I)c(C(=O)NCC(O)CO)c1I- InChIKey
NJKDOADNQSYQEV-UHFFFAOYSA-N- Molecular formula
- C17H22I3N3O8
- Average molar mass
- 777.1 g/mol
- Monoisotopic mass
- 776.8541
Overview
Iomeprol 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 glycoloyl(methyl)amino group at the 5-position. It has a role as a xenobiotic, a radioopaque medium and an environmental contaminant. It is an organoiodine compound and a benzenedicarboxamide.
Names & identifiers
- Preferred name
- Iomeprol
- IUPAC
- 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[(2-hydroxyacetyl)-methylamino]-2,4,6-triiodobenzene-1,3-dicarboxamide
- English name
- IOMEPROL
- Molecular formula
- C17H22I3N3O8
- Molecular weight
- 777.09
Names & synonyms
Show more names
Database identifiers
- CAS
78649-41-9- PubChem CID
- 3731
- DTXSID
DTXSID1049061- ChEMBL
CHEMBL2107214- ChEBI
CHEBI:31710- UNII
- 17E17JBP8L
- Nikkaji
- J277.762B
Properties
Computed structural properties
- XLogP
- -2.3
- Topological polar surface area
- 180 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 10
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 591
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Contrast Media; Diagnostic Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 263 · 263-265C
- Boiling point
- 813.2 · 813.2±65.0 °C(Predicted)
- Density
- 420 · d420 1.166; d437 1.161; d420 1.334; d437 1.329; d420 1.446; d437 1.441
- refractive index
- 20 · nD20 1.3828; nD20 1.4327; nD20 1.4660
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 11.36 · 11.36±0.46(Predicted)
- form
- Solid
- color
- White to Off-White
- InChI
- InChI=1S/C17H22I3N3O8/c1-23(9(29)6-26)15-13(19)10(16(30)21-2-7(27)4-24)12(18)11(14(15)20)17(31)22-3-8(28)5-25/h7-8,24-28H,2-6H2,1H3,(H,21,30)(H,22,31)
- InChIKey
- NJKDOADNQSYQEV-UHFFFAOYSA-N
- SMILES
- C1(C(NCC(O)CO)=O)=C(I)C(N(C(CO)=O)C)=C(I)C(C(NCC(O)CO)=O)=C1I
- CAS DataBase Reference
- 78649 · 78649-41-9(CAS DataBase Reference)
- FDA UNII
- 17 E17JBP8L · 17E17JBP8L
- ATC code
- 8 AB10 · V08AB10
- EPA Substance Registry System
- 1 · 1,3-Benzenedicarboxamide, N1,N3-bis(2,3-dihydroxypropyl)-5-[(2-hydroxyacetyl)methylamino]-2,4,6-triiodo- (78649-41-9)
- Toxicity
- 50 · LD50 (400 mgI/ml soln) i.v. in mice, rats (gI/kg): 19.9, 14.5; LD50 (370 mgI/ml soln) i.v. in dogs (gI/kg): >12.5 (Morisetti)
Safety & regulation
Toxicology
Safety data
- Toxicity
- LD50 (400 mgI/ml soln) i.v. in mice, rats (gI/kg): 19.9, 14.5; LD50 (370 mgI/ml soln) i.v. in dogs (gI/kg): >12.5 (Morisetti)
Chemistry & industry
Pharmacology
ATC Code
V08AB10
V - Various
QV - Various
Pharmacodynamics
The degree of radiographic enhancement by iomeprol is related to the iodine concentration in the tissue of interest following the administration of iomeprol. However, the exposure-response relationships and time course of pharmacodynamic response of iomeprol have not been fully characterized. At therapeutic concentrations, iomeprol was not shown to cause significant effects on the cardiovascular, central nervous, renal, and complement systems.
Mechanism of Action
Iomeprol is a radiographic iodinated contrast agent that opacifies the vessels and body structures where the contrast agent is present following intravenous or intra-arterial administration, permitting radiographic visualization of the internal structures through attenuation of X-ray photons. In imaging of the body, iodinated contrast agents diffuse from the vessels into the extravascular space. In normal brain with an intact blood-brain barrier, the contrast agent does not diffuse into the extravascular space and contrast enhancement is generally due to the presence of contrast within the vascular space. In patients with a disrupted blood-brain barrier, the contrast agent accumulates in the extravascular space in the region of disruption.
FDA Pharmacological Classification
17E17JBP8L
IOMEPROL
Established Pharmacologic Class [EPC] - Radiographic Contrast Agent
Mechanisms of Action [MoA] - X-Ray Contrast Activity
Iomeprol is a Radiographic Contrast Agent. The mechanism of action of iomeprol is as a X-Ray Contrast Activity.
IOMEPROL INJECTION
Absorption, Distribution and Excretion
The maximum concentration (Cmax) and area under the concentration-time curve (AUC) are doseproportional across the dose range of 250 mg iodine/kg to 1,250 mg iodine/kg body weight.
Approximately 90% of the iomeprol dose is excreted unchanged in urine within 24 hours.
The volume of distribution of iomeprol is 0.28 (0.05) L/kg. In rats, iomeprol was shown to cross the placenta and be excreted into breast milk.
The total body clearance is 0.10 (0.01) L/hr/kg.
Uses & manufacturing
Applications
UsesDiagnostic aid (radiopaque medium).
Upstream & downstream products
Upstream raw materials
Suppliers74 total
Additional notes
DefinitionChEBI: 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 glycoloyl(methyl)amino group at the 5-position.
Related reactions
No reaction records under the current filter.
Compound notes
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