Identification
- Summary
Ioversol is a diagnostic contrast agent used in various medical imaging procedures, such as angiography, urography, and computed tomographic scans.
- Brand Names
- Optiray
- Generic Name
- Ioversol
- DrugBank Accession Number
- DB09134
- Background
Ioversol is a non-ionic compound with a tri-iodinated benzene ring used as a contrast dye in diagnostic procedures to visualize different types of organs and tissues.2 Iodine has a high atomic density, which gives it the ability to attenuate X-rays.4 The intravascular administration of iodine compounds, such as ioversol, enhances the contrast between vessels in the path of the flow of the contrast medium and normal tissue, allowing the visualization of internal structures.2 Ioversol is a highly hydrophilic agent considered to be generally safe4; however, serious adverse reactions have been reported due to the inadvertent intrathecal administration of ioversol, which is only indicated for intra-arterial and intravenous use.2
Ioversol was approved by the FDA in 1989 and is currently indicated for computed tomographic (CT) imaging and contrast enhancement in peripheral arteriography, coronary arteriography, and left ventriculography.2,4
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ioversol (DB09134)
- Weight
- Average: 807.115
Monoisotopic: 806.86466 - Chemical Formula
- C18H24I3N3O9
- Synonyms
- Ioversol
- N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl) -glycolamido] -2,4,6-triiodoisophthalamide
- Optiray
- External IDs
- MP 328
- MP-328
- MP328
Pharmacology
- Indication
As the product Optiray 300, the intra-arterial use of ioversol is indicated for cerebral arteriography and peripheral arteriography in adults, while its intravenous use is indicated for CT imaging of the head and body, venography, and intravenous excretory urography in adults.2
As the product Optiray 320, the intra-arterial use of ioversol is indicated for cerebral arteriography, peripheral arteriography, visceral and renal arteriography, aortography, coronary arteriography, and left ventriculography in adults, and angiocardiography in pediatic patients.2 The intravenous use of this product is indicated for CT imaging of the head and body, venography, and intravenous excretory urography in adults and CT imaging of the head and body, and intravenous excretory urography in pediatric patients.2
As the product Optiray 350, the intra-arterial use of ioversol is indicated for peripheral arteriography coronary arteriography, and left ventriculography in adults, and angiocardiography in pediatic patients.2 The intravenous use of this product is indicated for CT imaging of the head and body, venography, intravenous excretory urography, and intravenous digital subtraction angiography (IV-DSA) in adults and CT imaging of the head and body, and intravenous excretory urography in pediatric patients.2
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The contrast enhancement obtained with ioversol is related to iodine content. Immediately after ioversol is injected, a peak in iodine plasma levels can be detected. However, depending on the organ being imaged, the time to maximum contrast will vary.2 The time to maximum contrast enhancement will range from the time iodine plasma levels reach their highest concentration to one hour after intravenous bolus administration. The delay between a peak in iodine plasma levels and maximum contrast enhancement is partly due to the accumulation of iodine-containing medium within a lesion and outside the blood pool.2
For angiographies, the maximum contrast enhancement of ioversol occurs almost immediately (15-120 seconds). Following rapid intravenous injection, ioversol can be visualized in the renal parenchyma within 30 to 60 seconds. In patients with normal renal function, opacification of the calyces and pelves takes place within 1-3 minutes, with an optimum contrast within 5-15 minutes.2
- Mechanism of action
Ioversol is a highly soluble non-ionic ionidated contrast agent. Intravascular injection of ioversol opacifies those vessels in the path of the flow of the contrast medium, allowing the radiographic visualization of the internal structures until significant hemodilution occurs.2 In imaging procedures, ioversol diffuses from the vascular to the extravascular space. In brains with an intact blood-brain barrier, this agent does not diffuse to the extravascular space. However, in patients with a disrupted blood-brain barrier, ioversol accumulates in the interstitial space of the disrupted region.2 As the product Optiray, ioversol enhances computed tomographic imaging through augmentation of radiographic efficiency with the degree of density enhancement directly related to the iodine content in an administered dose.3
- Absorption
Healthy volunteers that received 50 and 150 mL of ioversol, had a corresponding Cmax of 1.45 mg/mL and 2.36 mg/mL and a corresponding tmax of 2.0 min and 4.3 min.1 AUC was 1.74 mg⋅hr/mL in healthy volunteers that received 50 mL of ioversol, and 4.43 mg⋅hr/mL in those that received 150 mL.1 The pharmacokinetics of ioversol follow an open two compartment model with first-order elimination.3 Since ioversol is almost completely excreted by the kidney as a parent drug, patients with renal impairment are expected to have a lower elimination rate.2
- Volume of distribution
In adults, the volume of distribution of ioversol was 0.26 L/kg body weight, consistent with its extracellular space distribution2.
- Protein binding
Ioversol does not bind to serum or plasma proteins.2
- Metabolism
Ioversol does not undergo significant metabolism, deiodination or biotransformation.2
- Route of elimination
Following intravascular administration, ioversol is excreted mainly through the kidneys.3 Within the first 24 hours, more than 95% of the administered dose is excreted. Urine concentration peaks in the first 2 hours after ioversol is administered.2 Fecal elimination is negligible.3
- Half-life
The elimination half-life was 1.5 hr in healthy volunteers (n=12) receiving 50 and 150 mL of ioversol 68%.2 In patients with renal dysfunction, the elimination half-life of ioversol is prolonged.3
- Clearance
In healthy volunteers that received 50 mL of ioversol, clearance was 156 mL/min, and in those receiving 150 mL of ioversol, clearance was 185 mL/min.1
- Adverse Effects
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Ioversol overdosage causes life-threatening adverse effects, mainly in the pulmonary and cardiovascular system.2 In case of an overdose, treatment must focus on the support of vital functions and the prompt institution of symptomatic therapy.3 The carcinogenic potential of ioversol has not been evaluated, and non-clinical studies suggest that ioversol is not mutagenic and does not affect fertility.2 The LD50 values in mice and rats are 17 g/kg and 15 g/kg respectively. Developmental toxicity studies were carried out in rats (gestation day 7 to 17) and rabbits (gestation day 6 to 18) given ioversol at the following intravenous doses: 0, 0.2, 0.8, and 3.2 g iodine/kg/day. Adverse effects on embryo-fetal development were not detected in either species, while maternal toxicity was detected in rabbits at 0.8, and 3.2 g iodine/kg/day.2
Serious adverse reactions have been reported due to the inadvertent intrathecal administration of iodinated contrast media that are not indicated for intrathecal use such as ioversol. These serious adverse reactions include death, convulsions, cerebral hemorrhage, coma, paralysis, arachnoiditis, acute renal failure, cardiac arrest, seizures, rhabdomyolysis, hyperthermia, and brain edema.2 Caution must be exercised in patients with severely impaired renal function, combined renal and hepatic disease, severe thyrotoxicosis, myelomatosis, or anuria, particularly when large doses are administered.3
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Ioversol which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Ioversol which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Ioversol which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Ioversol which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Ioversol which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- OPTIRAY 300 (Liebel-Flarsheim) / OPTIRAY 320 (Liebel-Flarsheim) / OPTIRAY 350 (Liebel-Flarsheim)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Optiray 160 Injection 339 mg/1mL Intravascular Mallinckrodt Inc. 2007-03-23 2007-03-23 US 
Optiray 160 Solution 34 % Intravenous Tyco Healthcare 1992-12-31 2010-08-05 Canada 
Optiray 160 (ultraject) Solution 34 % Intravascular Tyco Healthcare Not applicable Not applicable Canada Optiray 240 Solution 51 % w/v Intravascular; Subarachnoid Liebel Flarsheim Company Llc 1996-11-20 Not applicable Canada Optiray 240 Injection 509 mg/1mL Intra-arterial; Intravenous Liebel-Flarsheim Company LLC 2012-03-04 2021-09-15 US
Categories
- ATC Codes
- V08AB07 — Ioversol
- Drug Categories
- Acids, Carbocyclic
- Benzene Derivatives
- Benzoates
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Iodinated Contrast Agents
- Iodobenzoates
- Radiographic Contrast Agent
- Roentgenography
- Watersoluble, Nephrotropic, Low Osmolar X-Ray Contrast Media
- X-Ray Contrast Activity
- X-Ray Contrast Media, Iodinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Acylaminobenzoic acid and derivatives
- Alternative Parents
- 2-halobenzoic acids and derivatives / 4-halobenzoic acids and derivatives / Anilides / Benzamides / Benzoyl derivatives / Iodobenzenes / Aryl iodides / Vinylogous halides / Tertiary carboxylic acid amides / Secondary alcohols show 8 more
- Substituents
- 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Acylaminobenzoic acid or derivatives / Alcohol / Alkanolamine / Anilide / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Benzamide show 21 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- N3RIB7X24K
- CAS number
- 87771-40-2
- InChI Key
- AMDBBAQNWSUWGN-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H24I3N3O9/c19-13-11(17(32)22-3-8(29)5-26)14(20)16(24(1-2-25)10(31)7-28)15(21)12(13)18(33)23-4-9(30)6-27/h8-9,25-30H,1-7H2,(H,22,32)(H,23,33)
- IUPAC Name
- N1,N3-bis(2,3-dihydroxypropyl)-5-[2-hydroxy-N-(2-hydroxyethyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide
- SMILES
- OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I
References
- Synthesis Reference
Bailey, AR., et al. (1993). Synthesis of ioversol (U.S. Patent No. 5,489,708). U.S. Patent and Trademark Office. https://patentimages.storage.googleapis.com/74/66/8e/1eddf38cd8cd41/US5489708.pdf
- General References
- Wilkins RA, Whittington JR, Brigden GS, Lahiri A, Heber ME, Hughes LO: Safety and pharmacokinetics of ioversol in healthy volunteers. Invest Radiol. 1989 Oct;24(10):781-8. doi: 10.1097/00004424-198910000-00011. [Article]
- FDA Approved Products: OPTIRAY (ioversol) injection for intravenous use [Link]
- FDA approval package: OPTIRAY (ioversol) injection [Link]
- Molecular Imaging and Contrast Agent Database (MICAD) [Internet]: Ioversol [Link]
- Toronto Research Chemicals: Ioversol SDS [Link]
- External Links
- KEGG Drug
- D01555
- PubChem Compound
- 3741
- PubChem Substance
- 310265049
- ChemSpider
- 3610
- 27792
- ChEBI
- 31717
- ChEMBL
- CHEMBL1200614
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ioversol
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Terminated Other Impaired Renal Function 1 4 Withdrawn Diagnostic Coronary Artery Disease (CAD) / Diabetes Mellitus / Impaired Renal Function 1 4 Withdrawn Other Hypothyroidism 1 1 Completed Treatment Osteoarthritis of the Knee 1 0 Completed Screening Acute Myeloid Leukemia / Chronic Myelogenous Leukemia (CML) / Multiple Myeloma (MM) / Myelodysplastic Syndrome 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution 300 MG/ML Injection, solution 320 MG/ML Injection, solution 350 MG/ML Injection, solution Intra-arterial; Intravenous 160 MG/ML Injection, solution Intra-arterial; Intravenous 240 MG/ML Injection, solution Intra-arterial; Intravenous 300 MG/ML Injection, solution Intra-arterial; Intravenous 320 MG/ML Injection, solution Intra-arterial; Intravenous 350 MG/ML Solution Intravenous 741 mg Injection Intravascular 339 mg/1mL Solution Intravenous 34 % Solution Intravascular 34 % Injection Intra-arterial; Intravenous 509 mg/1mL Solution Intravascular; Subarachnoid 51 % w/v Liquid Intravascular 240 mg / mL Injection, solution Parenteral Injection, solution Intra-arterial; Intravenous 509 mg/ml Solution Intra-arterial; Intravenous 509 mg/ml Injection Intra-arterial; Intravenous 636 mg/1mL Solution 300 mg/1ml Solution Intravascular 64 % w/v Solution Intra-arterial; Intravenous 636 mg/ml Injection Intra-arterial; Intravenous 678 mg/1mL Injection Intravascular Solution Intravascular 68 % w/v Solution 320 mg/1ml Solution Intra-arterial; Intravenous 678 mg/ml Injection Intra-arterial; Intravenous 741 mg/1mL Solution Intravascular 74 % w/v Solution 350 mg/1ml Injection Intravascular 741 mg/ml Injection, solution Intravascular 741 mg/ml Solution Intra-arterial; Intravenous 741 mg/ml Solution Intravenous 678 mg Injection - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 180-182°C SDS water solubility Water soluble FDA label logP -2.98 Howard, PH. Handbook of Physical Properties of Organic Chemicals, Part 1. CRC Press, 1996. p.1395. - Predicted Properties
Property Value Source Water Solubility 1.04 mg/mL ALOGPS logP -3 ALOGPS logP -2.1 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 11.72 Chemaxon pKa (Strongest Basic) -2.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 199.89 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 144.58 m3·mol-1 Chemaxon Polarizability 58.31 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 223.06244 predictedDeepCCS 1.0 (2019) [M+H]+ 225.42044 predictedDeepCCS 1.0 (2019) [M+Na]+ 231.51358 predictedDeepCCS 1.0 (2019)
Drug created at September 29, 2015 22:11 / Updated at April 24, 2024 14:30