Ioversol

Identification

Name
Ioversol
Accession Number
DB09134
Type
Small Molecule
Groups
Approved
Description

Ioversol is an organoiodine compound used as a diagnostic contrast medium. It features both a high iodine content, as well as several hydrophilic groups.

Structure
Thumb
Synonyms
  • N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl) -glycolamido] -2,4,6-triiodoisophthalamide
  • Optiray
External IDs
MP 328 / MP-328 / MP328
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Optiray 160Injection339 mg/1mLIntravascularMallinckrodt Inc.2007-03-232007-03-23Us
Optiray 160Solution34 %IntravenousTyco Healthcare1992-12-312010-08-05Canada
Optiray 160 (ultraject)Solution34 %IntravascularTyco HealthcareNot applicableNot applicableCanada
Optiray 240Injection509 mg/1mLIntra-arterial; IntravenousLiebel-Flarsheim Company LLC2012-03-04Not applicableUs
Optiray 240Solution51 %Intravascular; SubarachnoidLiebel Flarsheim Company Llc1996-11-20Not applicableCanada
Optiray 240 (ultraject)Solution51 %Intravascular; SubarachnoidLiebel Flarsheim Company Llc1996-12-31Not applicableCanada
Optiray 240 Inj 240mg/mlLiquid240 mgIntravascularMallinckrodt1992-12-312014-12-10Canada
Optiray 300Solution64 %IntravascularLiebel Flarsheim Company Llc1998-03-03Not applicableCanada
Optiray 300Injection636 mg/1mLIntra-arterial; IntravenousLiebel-Flarsheim Company LLC2011-10-17Not applicableUs
Optiray 300 (ultraject)Solution64 %IntravascularLiebel Flarsheim Company LlcNot applicableNot applicableCanada
Categories
UNII
N3RIB7X24K
CAS number
87771-40-2
Weight
Average: 807.115
Monoisotopic: 806.86466
Chemical Formula
C18H24I3N3O9
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

Pharmacology

Indication

Optiray 350 is indicated in adults for peripheral and coronary arteriography and left ventriculography. Optiray 350 is also indicated for contrast enhanced computed tomographic imaging of the head and body, intravenous excretory urography, intravenous digital subtraction angiography and venography. Optiray 350 is indicated in children for angiocardiography. Optiray 320 is indicated in adults for angiography throughout the cardiovascular system. The uses include cerebral, coronary, peripheral, visceral and renal arteriography, venography, aortography, and left ventriculography. Optiray 320 is also indicated for contrast enhanced computed tomographic imaging of the head and body, and intravenous excretory urography. Optiray 320 is indicated in children for angiocardiography, contrast enhanced computed tomographic imaging of the head and body, and intravenous excretory urography. Optiray 300 is indicated for cerebral angiography and peripheral arteriography. Optiray 300 is also indicated for contrast enhanced computed tomographic imaging of the head and body, venography, and intravenous excretory urography. Optiray 240 is indicated for cerebral angiography and venography. Optiray 240 is also indicated for contrast enhanced computed tomographic imaging of the head and body and intravenous excretory urography.

Pharmacodynamics
Not Available
Mechanism of action

Intravascular injection of ioversol opacifies those vessels in the path of the flow of the contrast medium, permitting radiographic visualization of the internal structures until significant hemodilution occurs. Optiray 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.

Absorption

Ioversol may be visualized in the renal parenchyma within 30 to 60 seconds following rapid intravenous injection. Opacification of the calyces and pelves in patients with normal renal function becomes apparent within 1 to 3 minutes, with optimum contrast occurring within 5 to 15 minutes.

Volume of distribution
Not Available
Protein binding

Ioversol does not bind to serum or plasma proteins.

Metabolism

No significant metabolism, deiodination or biotransformation occurs.

Route of elimination

Ioversol is excreted mainly through the kidneys following intravascular administration. Greater than 95% of the administered dose was excreted within the first 24 hours, with the peak urine concentration occurring in the first 2 hours after administration. Fecal elimination was negligible.

Half life

1.5 hr

Clearance
Not Available
Toxicity

Serious adverse reactions have been reported due to the inadvertent intrathecal administration of iodinated contrast media that are not indicated for intrathecal use. These serious adverse reactions include death, convulsions, cerebral hemorrhage, coma, paralysis, arachnoiditis, acute renal failure, cardiac arrest, seizures, rhabdomyolysis, hyperthermia, and brain edema. Serious, rarely fatal, thromboembolic events causing myocardial infarction and stroke have been reported during angiographic procedures with both ionic and nonionic contrast media. Therefore, meticulous intravascular administration technique is necessary, particularly during angiographic procedures, to minimize thromboembolic events. 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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Ioversol which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Ioversol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ioversol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ioversol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Ioversol which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ioversol which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Ioversol which could result in a higher serum level.
AcrivastineIoversol may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Ioversol which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Ioversol which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Morimoto S, Kozuka T, Takamiya M, Kimura K, Matsuyama S, Kuribayashi S, Shigeta A, Umemura J, Harada J, Yamada T, et al.: [Usefulness of ioversol (MP-328) in angiocardiography--a multicenter comparative study with iopamidol]. Nihon Igaku Hoshasen Gakkai Zasshi. 1990 Sep 25;50(9):1087-101. [PubMed:2247350]
External Links
KEGG Drug
D01555
PubChem Compound
3741
PubChem Substance
310265049
ChemSpider
3610
ChEBI
31717
ChEMBL
CHEMBL1200614
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ioversol
ATC Codes
V08AB07 — Ioversol
AHFS Codes
  • 36:68.00 — Roentgenography
FDA label
Download (6.99 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedScreeningLeukemia Acute Myeloid Leukemia (AML) / Leukemia, Myelogenous, Chronic / Multiple Myeloma (MM) / Myelodysplastic Syndromes1
4TerminatedDiagnosticCoronary Artery Disease / Diabetes Mellitus (DM) / Impaired Renal Function1
4TerminatedOtherImpaired Renal Function1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InjectionIntravascular339 mg/1mL
SolutionIntravenous34 %
SolutionIntravascular34 %
InjectionIntra-arterial; Intravenous509 mg/1mL
SolutionIntravascular; Subarachnoid51 %
LiquidIntravascular240 mg
InjectionIntra-arterial; Intravenous636 mg/1mL
SolutionIntravascular64 %
InjectionIntra-arterial; Intravenous678 mg/1mL
SolutionIntravascular68 %
InjectionIntra-arterial; Intravenous741 mg/1mL
SolutionIntravascular74 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 mg/mLALOGPS
logP-3ALOGPS
logP-2.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.89 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity144.58 m3·mol-1ChemAxon
Polarizability58.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Acylaminobenzoic acid or derivatives / 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Anilide / Benzamide / Benzoyl / Iodobenzene / Halobenzene / Aryl iodide
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on September 29, 2015 16:11 / Updated on November 18, 2018 13:32