Iohexol

Identification

Name
Iohexol
Accession Number
DB01362
Type
Small Molecule
Groups
Approved
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. [PubChem]

Structure
Thumb
Synonyms
  • Iohexolum
  • N,N'-Bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OmnipaqueSolution9 mg/1mLOralGe Healthcare2018-04-27Not applicableUs
OmnipaqueInjection140 mg/1mLIntravenousGe Healthcare2004-05-25Not applicableUs
OmnipaqueSolution518 mg/1mLIntravenousApothecary Shop Wholesale Inc.2011-06-012011-08-31Us
OmnipaqueInjection, solution350 mg/1mLIntravenousGe Healthcare1985-12-26Not applicableUs
OmnipaqueInjection240 mg/1mLIntravenousGe Healthcare1985-12-26Not applicableUs
OmnipaqueSolution388.3 mg/1mLIntravenousApothecary Shop Wholesale Inc.2011-07-012011-08-31Us
OmnipaqueInjection, solution300 mg/1mLIntravenousGe Healthcare1985-12-26Not applicableUs
OmnipaqueSolution12 mg/1mLOralGe Healthcare2018-04-27Not applicableUs
OmnipaqueInjection180 mg/1mLIntravenousGe Healthcare2004-07-15Not applicableUs
OmnipaqueSolution647.1 mg/1mLIntravenousApothecary Shop Wholesale Inc.2011-07-012011-08-31Us
International/Other Brands
Histodenz (Sigma) / Nycodenz
Categories
UNII
4419T9MX03
CAS number
66108-95-0
Weight
Average: 821.1379
Monoisotopic: 820.880309705
Chemical Formula
C19H26I3N3O9
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

Pharmacology

Indication

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

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]
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
DrugInteraction
AldesleukinThe risk of a hypersensitivity reaction to Iohexol is increased when it is combined with Aldesleukin.
MetforminThe risk or severity of adverse effects can be increased when Iohexol is combined with Metformin.
Food Interactions
Not Available

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]
External Links
Human Metabolome Database
HMDB0015449
PubChem Compound
3730
PubChem Substance
46506178
ChemSpider
3599
ChEBI
31709
ChEMBL
CHEMBL1200455
PharmGKB
PA450061
Wikipedia
Iohexol
ATC Codes
V08AB02 — Iohexol
AHFS Codes
  • 36:68.00 — Roentgenography

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1
1CompletedOtherRisk Factors for or a Diagnosis of Osteoporosis1
1CompletedTreatmentInfections, Human Immunodeficiency Virus and Tuberculosis1
1WithdrawnBasic ScienceImpaired Renal Function1
1, 2RecruitingDiagnosticBariatric Surgery Candidate / BMI >30 kg/m2 / Diabetes Complications / Diabetes Mellitus (DM) / Diabetic Kidney Disease / Diabetic Nephropathies / Obese experiencing rapid weight loss / Obesity, Adolescent / Pediatric Obesity / Renal Dysfunction / Type 2 Diabetes Mellitus1
1, 2RecruitingDiagnosticBMI >30 kg/m2 / Obesity, Adolescent / Renal Dysfunction / Type 2 Diabetes Mellitus1
1, 2RecruitingDiagnosticDiabetes Mellitus Complication / Diabetes, Autoimmune / Diabetes, Diabetes Mellitus Type 1 / Diabetic Nephropathies / Renal Dysfunction / Type 1 Insulin-Dependent Diabetes Mellitus1
2RecruitingBasic ScienceAcute Kidney Injury (AKI)1
2, 3RecruitingTreatmentProstate Cancer1
3CompletedDiagnosticAcute Circulatory Failure1
3CompletedTreatmentIschaemic Heart Diseases1
3RecruitingDiagnosticAcute Renal Failure (ARF)1
3RecruitingDiagnosticKnown or Suspected Abdominal Disease1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
4CompletedDiagnosticHealthy Volunteers1
4CompletedTreatmentInfection, Human Immunodeficiency Virus I1
4Not Yet RecruitingOtherHypothyroidism1
4RecruitingDiagnosticContrast Media Dosing1
4RecruitingDiagnosticSepsis1
Not AvailableActive Not RecruitingDiagnosticAll1
Not AvailableCompletedNot AvailableAging / Human Immunodeficiency Virus (HIV)1
Not AvailableCompletedNot AvailableImpaired Renal Function / Kidney Diseases1
Not AvailableRecruitingOtherAortic and Arterial Anomalies / Aortic Aneurysms / Contrast Induced Nephropathy (CIN)1
Not AvailableTerminatedNot AvailableMalignant Neoplasm of Pancreas1
Not AvailableTerminatedBasic ScienceFabry's Disease1
Not AvailableTerminatedDevice FeasibilityLung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC) / Lung Cancers / Mesothelioma1
Not AvailableTerminatedTreatmentIntestinal Obstruction1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • GE Healthcare Inc.
  • Hospira Inc.
  • Nycomed Inc.
Dosage forms
FormRouteStrength
InjectionIntravenous140 mg/1mL
InjectionIntravenous180 mg/1mL
InjectionIntravenous240 mg/1mL
Injection, solutionIntravenous300 mg/1mL
Injection, solutionIntravenous350 mg/1mL
SolutionIntravenous388.3 mg/1mL
SolutionIntravenous518 mg/1mL
SolutionIntravenous647.1 mg/1mL
SolutionOral12 mg/1mL
SolutionOral9 mg/1mL
SolutionSubarachnoid388 mg
LiquidSubarachnoid180 mg
SolutionIntravascular; Subarachnoid518 mg
LiquidIntravenous; Subarachnoid240 mg
SolutionIntravascular; Subarachnoid647 mg
LiquidIntravenous; Subarachnoid300 mg
SolutionIntravascular755 mg
LiquidIntravenous350 mg
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

Taxonomy

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
O-haloacetanilide / P-haloacetanilide / Halobenzene / Iodobenzene / Aryl halide / Aryl iodide / Acetamide / Tertiary carboxylic acid amide / Carboxamide group / Secondary alcohol
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organoiodine compound, benzenedicarboxamide (CHEBI:31709)

Drug created on July 06, 2007 13:54 / Updated on November 14, 2018 12:51