Iohexol

Identification

Name
Iohexol
Accession Number
DB01362
Description

Iohexol is an effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 821.1379
Monoisotopic: 820.880309705
Chemical Formula
C19H26I3N3O9
Synonyms
  • Iohexol
  • Iohexolum
  • N,N'-Bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide
External IDs
  • WIN 39424
  • WIN-39424

Pharmacology

Indication

Iohexol ia used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Iohexol is an effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality.

Mechanism of action

Organic iodine compounds block x-rays as they pass through the body, thereby allowing 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 intrathecal administration into the subarachnoid space, diffusion of iohexol in the CSF allows the visualization of the subarachnoid spaces of the head and spinal canal. After intravascular administration, iohexol makes opaque those vessels in its path of flow, allowing visualization of the internal structures until significant hemodilution occurs.

Absorption

Small amounts are absorbed through the bladder via intravesical instillation. Following intrauterine instillation, the majority of the medium within the uterine cavity is discharged into the vagina immediately upon termination of procedure. However, any medium retained in the uterine or peritoneal cavity is absorbed systemically within 60 minutes. May not be absorbed for up to 24 hours if tubes are obstructed and dilated.

Volume of distribution
  • 350-849 mL/kg
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Iohexol is absorbed from cerebrospinal fluid (CSF) into the bloodstream and is eliminated by renal excretion. No significant metabolism, deiodination, or biotransformation occurs.

Half-life

Intrathecal half-life is 3.4 hours (mean). Intravascular is approximately 2 hours (with normal renal function).

Clearance
  • 109 mL/min [Adult patients receiving 16-18 ml of iohexol (180 mgI/mL) by lumbar intrathecal injection]
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Non-ionic radiocontrast agents like iohexol 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
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Iohexol.
AldesleukinThe risk of a hypersensitivity reaction to Iohexol is increased when it is combined with Aldesleukin.
AmifampridineThe risk or severity of seizure can be increased when Iohexol is combined with Amifampridine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Iohexol.
BrexanoloneThe therapeutic efficacy of Brexanolone can be decreased when used in combination with Iohexol.
BrivaracetamThe therapeutic efficacy of Brivaracetam can be decreased when used in combination with Iohexol.
BupropionThe risk or severity of seizure can be increased when Bupropion is combined with Iohexol.
ButalbitalThe therapeutic efficacy of Butalbital can be decreased when used in combination with Iohexol.
CannabidiolThe therapeutic efficacy of Cannabidiol can be decreased when used in combination with Iohexol.
CarbamazepineThe therapeutic efficacy of Carbamazepine can be decreased when used in combination with Iohexol.
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

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

International/Other Brands
Histodenz (Sigma) / Nycodenz
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OmnipaqueSolution388.3 mg/1mLIntravenousApothecary Shop Wholesale Inc.2011-07-012011-08-31US flag
OmnipaqueInjection, solution240 mg/1mLIntra-articular; Intrathecal; Intravascular; Intravenous; Oral; RectalGE Healthcare Inc.1985-12-26Not applicableUS flag
OmnipaqueInjection, solution350 mg/1mLIntra-articular; Intravascular; Intravenous; OralGE Healthcare Inc.1985-12-26Not applicableUS flag
OmnipaqueSolution647.1 mg/1mLIntravenousApothecary Shop Wholesale Inc.2011-07-012011-08-31US flag
OmnipaqueSolution12 mg/1mLOralGE Healthcare Inc.2018-04-27Not applicableUS flag
OmnipaqueInjection, solution180 mg/1mLIntrathecal; Oral; RectalGE Healthcare Inc.2004-07-15Not applicableUS flag
OmnipaqueInjection, solution300 mg/1mLIntra-articular; Intrathecal; Intravascular; Intravenous; Oral; RectalGE Healthcare Inc.1985-12-26Not applicableUS flag
OmnipaqueSolution518 mg/1mLIntravenousApothecary Shop Wholesale Inc.2011-06-012011-08-31US flag
OmnipaqueSolution9 mg/1mLOralGE Healthcare Inc.2018-04-27Not applicableUS flag
OmnipaqueInjection, solution140 mg/1mLIntravascular; IntravenousGE Healthcare Inc.2004-05-25Not applicableUS flag
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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Categories

ATC Codes
V08AB02 — Iohexol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as o-haloacetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group, which is in turn ortho-substituted with a halogen atom.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
O-haloacetanilides
Alternative Parents
P-haloacetanilides / Iodobenzenes / Aryl iodides / Tertiary carboxylic acid amides / Acetamides / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Primary alcohols / Organopnictogen compounds
show 5 more
Substituents
Acetamide / Alcohol / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Carbonyl group / Carboxamide group / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid derivative
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organoiodine compound, benzenedicarboxamide (CHEBI:31709)

Chemical Identifiers

UNII
4419T9MX03
CAS number
66108-95-0
InChI Key
NTHXOOBQLCIOLC-UHFFFAOYSA-N
InChI
InChI=1S/C19H26I3N3O9/c1-8(29)25(4-11(32)7-28)17-15(21)12(18(33)23-2-9(30)5-26)14(20)13(16(17)22)19(34)24-3-10(31)6-27/h9-11,26-28,30-32H,2-7H2,1H3,(H,23,33)(H,24,34)
IUPAC Name
N1,N3-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide
SMILES
CC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I

References

Synthesis Reference

Xiu C. Wang, Steve A. Chamberlin, Ashok V. Bhatia, Gregg E. Robinson, John Hufnagel, "Process for the preparation of iohexol." U.S. Patent US5705692, issued December, 1985.

US5705692
General References
  1. Kawada TK: Iohexol and iopamidol: second-generation nonionic radiographic contrast media. Drug Intell Clin Pharm. 1985 Jul-Aug;19(7-8):525-9. [PubMed:3896713]
  2. Shaw DD, Potts DG: Toxicology of iohexol. Invest Radiol. 1985 Jan-Feb;20(1 Suppl):S10-3. [PubMed:3882609]
  3. FDA Approved Drug Products: OMNIPAQUE (iohexol) injection and oral solution. [Link]
Human Metabolome Database
HMDB0015449
KEGG Drug
D01817
PubChem Compound
3730
PubChem Substance
46506178
ChemSpider
3599
RxNav
5956
ChEBI
31709
ChEMBL
CHEMBL1200455
PharmGKB
PA450061
Wikipedia
Iohexol
AHFS Codes
  • 36:68.00 — Roentgenography

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticContrast Media Dosing1
4CompletedDiagnosticHealthy Volunteers1
4CompletedTreatmentCirrhosis Renal1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4Not Yet RecruitingOtherHypothyroidism1
4RecruitingBasic ScienceHeart Failure1
3CompletedDiagnosticAcute Circulatory Failure1
3CompletedTreatmentIschemic Heart Disease1
3RecruitingDiagnosticAcute Renal Failure (ARF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • GE Healthcare Inc.
  • Hospira Inc.
  • Nycomed Inc.
Dosage Forms
FormRouteStrength
InjectionIntra-arterial; Intrathecal; Intravenous647 mg/ml
Injection, solutionIntra-arterial; Intravenous755 mg/ml
Injection, solution15 g/50mL
Injection, solution17.5 g/50mL
Injection, solution30 g/100mL
SolutionIntra-arterial; Intrathecal; Intravenous300 mg/ml
SolutionIntra-arterial; Intrathecal; Intravenous350 mg/ml
SolutionIntra-articular; Intrathecal; Intravenous647 mg
Injection, solutionIntravenous647 mg
SolutionIntra-arterial; Intrathecal; Intravenous300 mg
Injection, solution35 g/100mL
Injection, solutionIntra-articular; Intrathecal; Intravascular; Intravenous; Oral; Rectal240 mg/1mL
Injection, solutionIntra-articular; Intrathecal; Intravascular; Intravenous; Oral; Rectal300 mg/1mL
Injection, solutionIntra-articular; Intravascular; Intravenous; Oral350 mg/1mL
Injection, solutionIntrathecal; Oral; Rectal180 mg/1mL
Injection, solutionIntravascular; Intravenous140 mg/1mL
Injection, solutionParenteral518 mg/ml
Injection, solutionParenteral647 mg/ml
Injection, solutionParenteral755 mg/ml
SolutionIntravenous388.3 mg/1mL
SolutionIntravenous518 mg/1mL
SolutionIntravenous647.1 mg/1mL
SolutionOral12 mg/1mL
SolutionOral9 mg/1mL
SolutionSubarachnoid
LiquidSubarachnoid
SolutionIntravascular; Subarachnoid
LiquidIntravenous; Subarachnoid
Injection, solutionIntrathecal647 mg
InjectionIntrathecal647 mg/ml
SolutionIntravascular
LiquidIntravenous
InjectionIntrathecal755 mg/ml
Injection
SolutionIntra-arterial; Intra-articular; Intrathecal; Intrauterine; Intravenous; Oral; Rectal300 mg
SolutionIntra-arterial; Intravenous350 mg
Injection, solutionIntravenous755 mg/ml
InjectionIntrathecal300 mg/mL
Injection, solutionIntravenous350 mg/mL
For solutionOral4.5 g/1
Prices
Unit descriptionCostUnit
Myelo-kit 180 mg/ml62.19USD each
Omnipaque 240 mg/ml vial5.34USD ml
Omnipaque 180 mg/ml vial4.92USD ml
Omnipaque 300 mg/ml vial4.82USD ml
Omnipaque 210 mg/ml vial3.53USD ml
Omnipaque 350 mg/ml cartridge2.29USD ml
Omnipaque 300 mg/ml cartridge2.17USD ml
Omnipaque 240 mg/ml cartridge1.77USD ml
Omnipaque 300 mg/ml syringe1.08USD ml
Omnipaque 350 mg/ml infu btl1.08USD ml
Omnipaque 140 mg/ml vial0.78USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)174-180 °CPhysProp
logP-3.05HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility0.796 mg/mLALOGPS
logP-2.8ALOGPS
logP-2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.89 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity148.84 m3·mol-1ChemAxon
Polarizability60.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier-0.5082
Caco-2 permeable-0.6474
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8375
P-glycoprotein inhibitor IINon-inhibitor0.8629
Renal organic cation transporterNon-inhibitor0.9534
CYP450 2C9 substrateNon-substrate0.7747
CYP450 2D6 substrateNon-substrate0.8175
CYP450 3A4 substrateNon-substrate0.6895
CYP450 1A2 substrateNon-inhibitor0.919
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9303
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.971
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7514
Ames testNon AMES toxic0.9035
CarcinogenicityNon-carcinogens0.8016
BiodegradationNot ready biodegradable0.9937
Rat acute toxicity1.6446 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9895
hERG inhibition (predictor II)Non-inhibitor0.7193
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
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0000000090-ec4e884f5d1e3e37a84f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0020002090-d8ff0c2813768e3cf012
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00dj-0009850000-7a1ca449a56d19c39ea8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fk9-0009120000-a8c863a64d387cfd461a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kmi-0496000000-bff588cc0e98918355e8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fu-0492000000-4a9469f17183d2f9f291
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0020003090-7423fd2df7e59f0f78ee
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fka-0008951000-ea0d52cf6d356a7f3590
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fk9-0029120000-e5ff4d33e064ff47ff49
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kmi-0395000000-775d49075e4ad66be119
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05i1-0492000000-1a8b12a2e372f5b00ca1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0000000090-262fc3f19d8442742408

Drug created on July 06, 2007 13:54 / Updated on October 21, 2020 01:55

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