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Iopromide

Alias: Ultravist SHL 414C Iopromide SHL 414C Ultravist UNII-712BAC33MZ ZK 35760.
Cat No.:V17241 Purity: ≥98%
Iopromide (trade nameUltravist), a non-ionic contrast agent, isan iodinated contrast medium used for X-ray imaging.
Iopromide
Iopromide Chemical Structure CAS No.: 73334-07-3
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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Product Description

Iopromide (trade name Ultravist), a non-ionic contrast agent, is an iodinated contrast medium used for X-ray imaging. It is a low osmolar, non-ionic contrast agent for intravascular use. Iopromide can be used in radiographic studies such as intravenous urograms, brain computer tomography and CT pulmonary angiograms.

Biological Activity I Assay Protocols (From Reference)
ln Vivo
An iopromide tail vein injection can cause contrast-induced nephropathy [1]. The overall picture quality and diagnostic quality in randomized controlled studies were shown to be on par with other low-penetration contrast agents such as iodixanol, or the isotonic contrast agent iohexol, iopromide, iopamidol, iomepropanol, and ioxagate. imaging using radiography. Extensive postmarketing surveillance studies have verified that iodobitol is an effective contrast agent in the great majority of patients and generates good or exceptional opacification. Iodopidol shares tolerance traits with other low- and isotonic contrast agents, and it is generally well tolerated. Iodobitol is therefore a useful intravascular medication for improving contrast in diagnostic imaging [2].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Immediately following intravascular injection, iopromide reaches peak plasma concentrations and is then rapidly distributed throughout the extracellular fluid compartment. It displays little tendency to bind to serum or plasma proteins. Iodinated contrast agents cross a disrupted blood-brain barrier.
The amounts excreted unchanged in urine represent 97% of the dose in adult healthy subjects. Only 2% of the dose is recovered in the feces. Similar recoveries in urine and feces are observed in middle-aged and elderly patients. This finding suggests that, compared to the renal route, biliary and/or gastrointestinal excretion is not important for iopromide. During the slower terminal phase, only 3% of the dose is eliminated; 97% of the dose is disposed of during the earlier phases, the largest part of which occurs during the main elimination phase. The ratio of the renal clearance of iopromide to the creatinine clearance is 0.82, suggesting that iopromide is mainly excreted by glomerular filtration. Additional tubular reabsorption is possible.
The total volume of distribution at steady state is about 16 L, suggesting distribution into extracellular space.
The mean total and renal clearances are 107 mL/min and 104 mL/min, respectively.
Metabolism / Metabolites
Iopromide does not undergo significant metabolism, deiodination, or biotransformation.
Biological Half-Life
After intravenous administration to healthy adult subjects, the plasma iopromide concentration-time profile shows an initial distribution phase with a half-life of 0.24 hours; a main elimination phase with a half-life of 2 hours; and a terminal elimination phase with a half-life of 6.2 hours.
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Intravenous iodinated contrast media are poorly excreted into breastmilk and poorly absorbed orally so they are not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants. Guidelines developed by several professional organizations state that breastfeeding need not be disrupted after a nursing mother receives an iodine-containing contrast medium. However, because there is no published experience with iopromide during breastfeeding, other agents may be preferred, especially while nursing a newborn or preterm infant.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Protein Binding
The plasma protein binding of iopromide is 1%.
References
[1]. Jiang W, et al. Breviscapine attenuatted contrast medium-induced nephropathy via PKC/Akt/MAPK signalling in diabetic mice. Am J Transl Res. 2016 Feb 15;8(2):329-41.
[2]. McCormack PL, et al. Iobitridol: a review of its use as a contrast medium in diagnostic imaging. Clin Drug Investig. 2013 Feb;33(2):155-66
Additional Infomation
Iopromide is a dicarboxylic acid diamide that consists of N-methylisophthalamide bearing three iodo substituents at positions 2, 4 and 6, a methoxyacetyl substituent at position 5 and two 2,3-dihydroxypropyl groups attached to the amide nitrogens. A water soluble x-ray contrast agent for intravascular administration. It has a role as a radioopaque medium, a nephrotoxic agent, a xenobiotic and an environmental contaminant. It is an organoiodine compound and a dicarboxylic acid diamide. It is functionally related to an isophthalamide and a glycerol.
Iopromide is a low osmolar, non-ionic X-ray contrast agent for intravascular administration. It functions as a contrast agent by opacifying blood vessels in the flow path of the contrast agent, permitting radiographic visualization of the internal structures until significant hemodilution occurs. Although iopromide can cause several serious adverse effects, including cardiac events, thromboembolism, hypersensitivity reaction, and even death if administered intrathecally inadvertently, it is still deemed to have a favorable safety profile, with only 0.7% of patients in a 2 years study experiencing adverse events. Although the mechanism is unclear, women and outpatients tend to have a higher incidence of adverse events compared to other population groups. Approved by the FDA in 1995 and Health Canada in 1994 under the brand name ULTRAVIST, iopromide is used in radiological diagnosis, including, but not limited to, intra-arterial digital subtraction angiography (IA-DSA), cerebral and peripheral arteriography, peripheral venography, excretory urography, brain computer tomography (CT), coronary arteriography, left ventriculography, visceral angiography, and orthography.
Iopromide is a Radiographic Contrast Agent. The mechanism of action of iopromide is as a X-Ray Contrast Activity.
Iopromide is a contrast medium.
Drug Indication
Iopromide, as the product IOVIST, is approved by the FDA for use as an intra-arterial or intravenous X-ray contrast agent. For intra-arterial administration, iopromide is indicated for cerebral arteriography, peripheral arteriography, coronary arteriography, left ventriculography, visceral angiography, and aortography in adults and radiographic evaluation of cardiac chambers and related arteries in pediatric patients aged 2 years and older. For intravenous administration, iopromide is indicated for excretory urography in adults and pediatric patients aged 2 years and older, contrast Computed Tomography (CT) of the head and body (intrathoracic, intra-abdominal, and retroperitoneal regions) for the evaluation of neoplastic and non-neoplastic lesions in adults and pediatric patients aged 2 years and older, and contrast mammography to visualize known or suspected lesions of the breast in adults, as an adjunct following mammography and/or ultrasound. Iopromide is also approved by Health Canada as an intravascular contrasting agent, although the indications differ depending on the dosage. At 300 mg I/mL, iopromide is indicated for computed tomography (CT), excretory urography, pediatric excretory urography, renal arteriography, peripheral arteriography (bifemoral pelvis/leg), cerebral arteriography, phlebography of the extremities, and arthrography.
FDA Label
Mechanism of Action
Iopromide is a nonionic iodinated, water-soluble, radiographic contrast medium that is available in two stable, ready-to-use solutions of different concentrations (i.e., 300 mg I/mL and 370 mg I/mL). Following intravascular injection, iopromide provides radiographic opacification of the vasculature and extracellular space in the path of flow of the agent, allowing diagnostic assessment of the limbs and internal organs until significant dilution occurs.
Pharmacodynamics
After intravenous injection, opacification of the renal parenchyma begins within 1 minute. Excretion of the contrast agent becomes apparent in 1 to 3 minutes with optimal contrast in the calyces and collecting system occurring between 5 and 15 minutes. In nephropathic conditions, particularly when excretory capacity has been altered, the excretion rate varies unpredictably and opacification may be delayed for several hours after injection. the degree of contrast enhancement is related to the iodine concentration in the tissue of interest.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H24I3N3O8
Molecular Weight
791.11
Exact Mass
790.869
CAS #
73334-07-3
Related CAS #
Iopromide-d3
PubChem CID
3736
Appearance
White to off-white solid powder
Density
2.2±0.1 g/cm3
Boiling Point
840.9±65.0 °C at 760 mmHg
Melting Point
broad (160ºC transition)
Flash Point
462.4±34.3 °C
Vapour Pressure
0.0±3.3 mmHg at 25°C
Index of Refraction
1.710
LogP
-2.95
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
11
Heavy Atom Count
32
Complexity
647
Defined Atom Stereocenter Count
0
SMILES
IC1=C(C(N([H])C([H])([H])C([H])(C([H])([H])O[H])O[H])=O)C(=C(C(=C1C(N(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])O[H])O[H])=O)I)N([H])C(C([H])([H])OC([H])([H])[H])=O)I
InChi Key
DGAIEPBNLOQYER-IUCAKERBSA-N
InChi Code
InChI=1S/C18H24I3N3O8/c1-24(4-9(28)6-26)18(31)12-13(19)11(17(30)22-3-8(27)5-25)14(20)16(15(12)21)23-10(29)7-32-2/h8-9,25-28H,3-7H2,1-2H3,(H,22,30)(H,23,29)/t8-,9-/m0/s1
Chemical Name
1,3-Benzenedicarboxamide, N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-((methoxyacetyl)amino)-N-methyl-
Synonyms
Ultravist SHL 414C Iopromide SHL 414C Ultravist UNII-712BAC33MZ ZK 35760.
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~126.40 mM)
H2O : ~100 mg/mL (~126.40 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (3.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (126.40 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2640 mL 6.3202 mL 12.6405 mL
5 mM 0.2528 mL 1.2640 mL 2.5281 mL
10 mM 0.1264 mL 0.6320 mL 1.2640 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
Pediatric Risk of Hypothyroidism With Iodinated Contrast Media
CTID: NCT03631771
Phase: Phase 4    Status: Withdrawn
Date: 2022-04-20
A Study to Learn More About the Safety of Ultravist in Children and in the Elderly
CTID: NCT04605471
Phase:    Status: Completed
Date: 2021-07-20
Role of Perfusion CT in Pancreatic Cancer
CTID: NCT01703650
Phase:    Status: Unknown status
Date: 2020-10-08
Study on the Risk of Allergy-like Reactions After Intra-arterial or Intra-venous Injection of the Marketed X-ray Contrast Medium Iopromid
CTID: NCT03622801
Phase:    Status: Completed
Date: 2020-02-17
A Non-interventiona
Xenetix 350 : comparative assessment of image quality for coronary CT angiography
CTID: null
Phase: Phase 4    Status: Completed
Date: 2010-10-19
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Isotonic contrast (iodixanol) administration vs. low osmolar contrast (iopromide) use: evaluating risk of contrast-induced nephropathy in cancer patients at very low risk
CTID: null
Phase: Phase 3    Status: Ongoing
Date: 2010-04-26


Renal haemodynamics during application of contrast media in patients undergoing cardiac catheterisation with high risk of acute renal failure: randomized comparison of different contrast media
CTID: null
Phase: Phase 4    Status: Completed
Date: 2005-09-09

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