Iodine based contrasting agent: IOMEPROL

IOMEPROL:

Active  name:IOMEPROL
Brand name:IOMERVU
Innovator nameBRACCO DIAGNOSTICS INC
Approval Date:NOV 27, 2024
Therapeutic activity:  Tri-iodinated X-Ray contrasting agent. Iomeprol has been investigated for the diagnostic of Coronary Artery Disease.
Route of administrationIntra arterial/intravenous, Injection
Structure
Chemical nameN,N’-bis(2,3-dihydroxypropyl)-5-[(hydroxyacetyl)- methylamino]-2,4,6-tri-iodo-1,3-benzenedicarboxamide.
CAS
78649-41-9
DosageAvailable in four iodine concentration. 510 mg (250 mg rebound iodine), 612 mg (300 mg rebound iodine); 714 mg (350 mg rebound iodine); 816 mg (400 mg rebound iodine);
Molecular weight& molecular formuale777.09 g/mol & C17H22I3N3O(Iodine content 49%)
Solubilitywater
NCE11/27/2029
Solubility dataSoluble in water.
HygroscopicityNot hygroscopic
DrugbankDB11705
Chemspider3600
Pubchem CID3731

Synthesis of Iomeprol:

ROS-1: Ref: EP 0026281A1

Iomeprol started with  commercially available 5-amino-2,4,6-triiodoisophthalic acid, which was couple with formamide followed by thionoyl  chloride to get the corresponding acid chloride. Coupling of acid chloride with 3-amino-1,2-propylene glycol to achieve the Iomeprol.

1H-NMR (DMSO-D 6)δ(ppm):2.91(s, 4H),3.21-3.36(m, 4H), 3.41-3.65(m, 4H), 3.85(s, 2H), 3.98(m,2H), 4.1-4.5(m,5H), 8.2-8.4(d, 2H); 13C-NMR(D 2O)δ(ppm)33.2,44.7,60.7,64.6,71.2,90.1,99.8,99.9,145.5,150.5,150.6,171.3,171.4,173.9.

ROS-2: CN 102363600B

Iomeprol started with  commercially available 5-amino-2,4,6-triiodoisophthalic acid, which was couple with thionoyl chloride followed bychloro acetyl   chloride to get the corresponding acid chloride. Coupling of acid chloride with 3-amino-1,2-propylene glycol, followed by treated with the sodium acetate to achieve the Iomeprol.

References:

1)      US4352788A

2)      CN101654417A

3)      CN106316878B

4)      CN107253918A

5)      KR102128423B1

6)      CN113387832A

7)      CN114213273A

8)      CN102363600B

9)      EP3854780A1

10)  KR2020/77762

11)  KR20170123748A 

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