Iodixanol

Identification

Summary

Iodixanol is a contrast agent used during coronary angiography, particularly in patients with renal dysfunction.

Brand Names
Visipaque, Visipaque 270, Visipaque 320
Generic Name
Iodixanol
DrugBank Accession Number
DB01249
Background

Iodixanol is a nonionic hydrophilic compound commonly used as a contrast agent during coronary angiography, particularly in individuals with renal dysfunction, as it is believed to be less toxic to the kidneys than most other intravascular contrast agents.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 1550.1819
Monoisotopic: 1549.713275288
Chemical Formula
C35H44I6N6O15
Synonyms
  • 5,5'-((2-hydroxytrimethylene)bis(acetylimino))bis(N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)
  • Indixanol
  • Iodixanol
  • Iodixanolum

Pharmacology

Indication

Iodixanol is a contrast agent during coronary angiography.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Iodixanol is a contrast agent commonly used during coronary angiography, particularly in individuals with renal dysfunction, as it is believed to be less toxic to the kidneys than most other intravascular contrast agents. It is an imaging contrast agent with the same osmolality as blood (290mOsm/kg H20).

Mechanism of action

Organic iodine compounds attenuate x-rays as they pass through the body, thereby allowing the body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. After intravascular administration, iodixanol makes opaque those internal structures in its path of flow, allowing their visualization until significant hemodilution and elimination occur.

Absorption

Not Available

Volume of distribution
  • 0.26 L/kg
Protein binding

Negligible

Metabolism

Excreted unchanged

Route of elimination

In adults, approximately 97% of the injected dose of iodixanol is excreted unchanged in urine within 24 hours, with less than 2% excreted in feces within five days post-injection.

Half-life

2.1 hours. In patients with significantly impaired renal function (mean creatinine clearance rate, 9.91 [± 3.58] mL per minute), the plasma half-life is increased to 23 hours.

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Non-ionic radiocontrast agents like iodixanol are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress.

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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Iodixanol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Iodixanol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Iodixanol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Iodixanol which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Iodixanol which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Iodixanol which could result in a higher serum level.
AclidiniumIodixanol may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineIodixanol may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Iodixanol which could result in a higher serum level.
Adefovir dipivoxilAdefovir dipivoxil may decrease the excretion rate of Iodixanol which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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International/Other Brands
Visipaque / Visipaque 270 / Visipaque 320
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VisipaqueInjection, solution320 mg/1mLIntravascularGE Healthcare Inc.2003-09-09Not applicableUS flag
VisipaqueInjection, solution270 mg/1mLIntravascularGE Healthcare Inc.2002-12-13Not applicableUS flag
Visipaque 270Solution550 mg / mLIntra-arterial; IntravenousGe Healthcare1995-12-31Not applicableCanada flag
Visipaque 320Solution652 mg / mLIntra-arterial; IntravenousGe Healthcare1995-12-31Not applicableCanada flag

Categories

ATC Codes
V08AB09 — Iodixanol
Drug Categories
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
P-haloacetanilides / O-haloacetanilides / 2-halobenzoic acids and derivatives / 4-halobenzoic acids and derivatives / Benzamides / Benzoyl derivatives / Iodobenzenes / Aryl iodides / Vinylogous halides / Tertiary carboxylic acid amides
show 10 more
Substituents
2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Acetamide / Acetanilide / Acylaminobenzoic acid or derivatives / Alcohol / Anilide / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide
show 25 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organoiodine compound (CHEBI:31705)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
HW8W27HTXX
CAS number
92339-11-2
InChI Key
NBQNWMBBSKPBAY-UHFFFAOYSA-N
InChI
InChI=1S/C35H44I6N6O15/c1-13(52)46(30-26(38)20(32(59)42-3-15(54)9-48)24(36)21(27(30)39)33(60)43-4-16(55)10-49)7-19(58)8-47(14(2)53)31-28(40)22(34(61)44-5-17(56)11-50)25(37)23(29(31)41)35(62)45-6-18(57)12-51/h15-19,48-51,54-58H,3-12H2,1-2H3,(H,42,59)(H,43,60)(H,44,61)(H,45,62)
IUPAC Name
5-{N-[3-(N-{3,5-bis[(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodophenyl}acetamido)-2-hydroxypropyl]acetamido}-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
SMILES
CC(=O)N(CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I

References

Synthesis Reference

Ole Homestad, "Preparation of iodixanol." U.S. Patent US20020010368, issued January 24, 2002.

US20020010368
General References
  1. Spencer CM, Goa KL: Iodixanol. A review of its pharmacodynamic and pharmacokinetic properties and diagnostic use as an x-ray contrast medium. Drugs. 1996 Dec;52(6):899-927. [Article]
  2. McCullough PA: Renal safety of iodixanol. Expert Rev Cardiovasc Ther. 2006 Sep;4(5):655-61. [Article]
Human Metabolome Database
HMDB0015379
KEGG Drug
D01474
PubChem Compound
3724
PubChem Substance
46504687
ChemSpider
3593
RxNav
27729
ChEBI
31705
ChEMBL
CHEMBL1200507
PharmGKB
PA164783998
Drugs.com
Drugs.com Drug Page
Wikipedia
Iodixanol
FDA label
Download (247 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableCoronary Artery Disease (CAD)1
4CompletedNot AvailableDrug Safety1
4CompletedNot AvailablePatient Comfort and Safety1
4CompletedDiagnosticAnatomic renal artery stenosis / Chronic Kidney Disease (CKD) / Pulmonary Cancer / Pulmonary Embolism1
4CompletedDiagnosticCoronary Artery Disease (CAD)1
4CompletedDiagnosticCoronary Artery Disease (CAD) / Deteriorating renal function1
4CompletedDiagnosticCoronary Artery Stenosis2
4CompletedDiagnosticDiagnostic Imaging1
4CompletedDiagnosticPeripheral Arterial Occlusive Disease (PAOD)2
4CompletedPreventionAcute Myocardial Infarction (AMI) / Prophylaxis of Contrast-induced nephropathy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • GE Healthcare Inc.
Dosage Forms
FormRouteStrength
InjectionParenteral
InjectionIntra-arterial; Intrathecal; Intravenous
InjectionIntravascular
Injection, solutionIntravascular270 mg/1mL
Injection, solutionIntravascular320 mg/1mL
Injection, solutionParenteral305 mg/ml
Injection, solutionParenteral550 mg/ml
Injection, solutionParenteral652 mg/ml
SolutionIntra-arterial; Intravenous550 mg / mL
Injection, solutionIntra-arterial; Intrathecal; Intravenous
Solution270 mg/1ml
SolutionIntra-arterial; Intrathecal; Intravenous270 mg
SolutionIntra-arterial; Intravenous652 mg / mL
SolutionIntra-arterial; Intrathecal; Intravenous320 mg
Solution320 mg/1ml
InjectionIntra-arterial; Intrathecal; Intravenous550 mg/ml
InjectionIntra-arterial; Intrathecal; Intravenous652 mg/ml
Prices
Unit descriptionCostUnit
Visipaque 320 mg/ml cartridge1.92USD ml
Visipaque 270 mg/ml cartridge1.57USD ml
Visipaque 320 mg/ml vial1.23USD ml
Visipaque 270 mg/ml vial1.13USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5366722No1994-11-222011-11-22US flag
USRE36418No1999-11-302011-07-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.185 mg/mLALOGPS
logP-2.9ALOGPS
logP-2.1ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)11.43ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area339.09 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity277.16 m3·mol-1ChemAxon
Polarizability111.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8058
Blood Brain Barrier-0.6467
Caco-2 permeable-0.6448
P-glycoprotein substrateSubstrate0.5344
P-glycoprotein inhibitor INon-inhibitor0.6189
P-glycoprotein inhibitor IINon-inhibitor0.6578
Renal organic cation transporterNon-inhibitor0.9372
CYP450 2C9 substrateNon-substrate0.7589
CYP450 2D6 substrateNon-substrate0.8157
CYP450 3A4 substrateNon-substrate0.5826
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5808
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6966
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.7030 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9948
hERG inhibition (predictor II)Non-inhibitor0.521
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Drug created on March 30, 2007 07:03 / Updated on October 20, 2021 19:48