Iodixanol

Identification

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Name
Iodixanol
Accession Number
DB01249
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • 5,5'-((2-hydroxytrimethylene)bis(acetylimino))bis(N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)
  • Indixanol
  • Iodixanol
  • Iodixanolum
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VisipaqueSolution652 mgIntra-arterial; IntravenousGe Healthcare1995-12-31Not applicableCanada
VisipaqueSolution550 mgIntra-arterial; IntravenousGe Healthcare1995-12-31Not applicableCanada
VisipaqueInjection, solution320 mg/1mLIntravascularGE Healthcare Inc.2010-06-01Not applicableUs
VisipaqueInjection, solution270 mg/1mLIntravascularGE Healthcare Inc.2009-03-012017-08-18Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Visipaque / Visipaque 270 / Visipaque 320
Categories
UNII
HW8W27HTXX
CAS number
92339-11-2
Weight
Average: 1550.1819
Monoisotopic: 1549.713275288
Chemical Formula
C35H44I6N6O15
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

Pharmacology

Indication

Iodixanol is a contrast agent during coronary angiography.

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.

Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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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
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.

Affected organisms
  • Humans and other mammals
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.
AcarboseAcarbose 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.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

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. [PubMed:8957160]
  2. McCullough PA: Renal safety of iodixanol. Expert Rev Cardiovasc Ther. 2006 Sep;4(5):655-61. [PubMed:17081087]
External Links
Human Metabolome Database
HMDB0015379
KEGG Drug
D01474
PubChem Compound
3724
PubChem Substance
46504687
ChemSpider
3593
ChEBI
31705
ChEMBL
CHEMBL1200507
PharmGKB
PA164783998
Drugs.com
Drugs.com Drug Page
Wikipedia
Iodixanol
ATC Codes
V08AB09 — Iodixanol
AHFS Codes
  • 36:68.00 — Roentgenography
FDA label
Download (247 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedPreventionContrast Induced Acute Kidney Injury1
1TerminatedDiagnosticHealthy Volunteers1
1, 2CompletedDiagnosticHealthy Volunteers1
3CompletedDiagnosticAtherosclerosis / Carotid Artery Plaque / Stroke, Ischemic1
3CompletedDiagnosticCoronary Artery Disease2
3CompletedDiagnosticCoronary Computed Tomographic Angiography1
4CompletedNot AvailableCoronary Artery Disease1
4CompletedNot AvailableDrug Safety1
4CompletedNot AvailablePatient Comfort and Safety1
4CompletedDiagnosticAnatomic renal artery stenosis / Chronic Kidney Disease (CKD) / Pulmonary Cancer / Pulmonary Embolism1
4CompletedDiagnosticCoronary Artery Disease1
4CompletedDiagnosticCoronary Artery Disease / Impaired kidney function1
4CompletedDiagnosticCoronary Artery Stenosis2
4CompletedDiagnosticDiagnostic Imaging1
4CompletedDiagnosticPeripheral Obliterative Arteriopathy2
4CompletedPreventionAcute Myocardial Infarction (AMI) / Contrast Induced Nephropathy (CIN)1
4CompletedPreventionAngioplasty, Transluminal, Percutaneous Coronary / Coronary Arteriosclerosis / Renal Insufficiency,Chronic1
4CompletedPreventionChronic Renal Failure (CRF)1
4CompletedPreventionRadiocontrast-Induced Nephropathy1
4CompletedPreventionRenal Failure1
4CompletedTreatmentBack Pain Lower Back Chronic1
4CompletedTreatmentCoronary Angiography / Renal Insufficiency,Chronic1
4Not Yet RecruitingOtherHypothyroidism1
4TerminatedDiagnosticChronic Renal Diseases1
4TerminatedDiagnosticCoronary Artery Stenosis1
4TerminatedDiagnosticDiabetes Mellitus / Renal Insufficiency,Chronic1
4TerminatedDiagnosticDiabetes Mellitus / Impaired kidney function1
4TerminatedOtherChronic Kidney Disease (CKD)1
4TerminatedOtherImpaired kidney function1
4Unknown StatusPreventionChronic Renal Failure (CRF)1
4WithdrawnDiagnosticCoronary Artery Disease / Diabetes Mellitus / Impaired kidney function1
Not AvailableActive Not RecruitingPreventionCardio-Renal Syndrome1
Not AvailableCompletedDiagnosticAbdominal Aortic Aneurysms (AAA)1
Not AvailableCompletedDiagnosticAortic Valve Stenosis1
Not AvailableCompletedPreventionCardio-Renal Syndrome1
Not AvailableRecruitingNot AvailableCoronary Artery Disease / ST Segment Elevation Myocardial Infarction (STEMI)1
Not AvailableTerminatedNot AvailableMalignant Neoplasm of Pancreas1
Not AvailableTerminatedDevice FeasibilityLung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC) / Lung Cancers / Mesothelioma1
Not AvailableWithdrawnDiagnosticMultiple Pulmonary Emboli1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • GE Healthcare Inc.
Dosage forms
FormRouteStrength
Injection, solutionIntravascular270 mg/1mL
Injection, solutionIntravascular320 mg/1mL
SolutionIntra-arterial; Intravenous550 mg
SolutionIntra-arterial; Intravenous652 mg
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)
US5366722No1994-11-222011-11-22Us
USRE36418No1999-11-302011-07-12Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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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

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
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
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Substituents
Acylaminobenzoic acid or derivatives / O-haloacetanilide / P-haloacetanilide / Haloacetanilide / Acetanilide / 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Benzamide / Anilide
show 25 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organoiodine compound (CHEBI:31705)

Drug created on March 30, 2007 01:03 / Updated on January 24, 2020 15:33