Iodixanol

Identification

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
  • Iodixanolum
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VisipaqueInjection, solution320 mg/1mLIntravascularGe Healthcare2003-09-09Not applicableUs
VisipaqueSolution550 mgIntra-arterial; IntravenousGe Healthcare1995-12-31Not applicableCanada
VisipaqueInjection, solution270 mg/1mLIntravascularGe Healthcare2002-12-13Not applicableUs
VisipaqueSolution652 mgIntra-arterial; IntravenousGe Healthcare1995-12-31Not applicableCanada
International/Other Brands
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 iso-osmolar contrast agent, with an osmolality of 290 mOsm/kg H20, the same as blood.

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
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
DrugInteractionDrug group
AcetaminophenAcetaminophen may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
AldesleukinThe risk of a hypersensitivity reaction to Iodixanol is increased when it is combined with Aldesleukin.Approved
AlprazolamAlprazolam may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Illicit, Investigational
AmilorideAmiloride may increase the excretion rate of Iodixanol which could result in a lower serum level and potentially a reduction in efficacy.Approved
AmlodipineAmlodipine may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
AmoxicillinAmoxicillin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
AmphetamineAmphetamine may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Illicit, Investigational
AmpicillinAmpicillin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
AuranofinAuranofin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
BaclofenBaclofen may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
BudesonideBudesonide may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
BumetanideBumetanide may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
CevimelineCevimeline may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
ChlorpromazineChlorpromazine may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational, Vet Approved
ChlorzoxazoneChlorzoxazone may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
ClonazepamIodixanol may decrease the excretion rate of Clonazepam which could result in a higher serum level.Approved, Illicit
ClorazepateClorazepate may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Illicit
CyanocobalaminCyanocobalamin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Nutraceutical
DaptomycinDaptomycin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
DiazepamDiazepam may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Illicit, Investigational, Vet Approved
DiclofenacDiclofenac may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
DiflunisalDiflunisal may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
DoxycyclineDoxycycline may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational, Vet Approved
EthambutolEthambutol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
FluconazoleFluconazole may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
FlurbiprofenFlurbiprofen may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
Folic AcidFolic Acid may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Nutraceutical, Vet Approved
GentamicinGentamicin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
HaloperidolHaloperidol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
HydralazineIodixanol may decrease the excretion rate of Hydralazine which could result in a higher serum level.Approved
HydroxocobalaminHydroxocobalamin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
IbuprofenIbuprofen may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
IcosapentIcosapent may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Nutraceutical
ImipramineIodixanol may decrease the excretion rate of Imipramine which could result in a higher serum level.Approved
IndomethacinIndomethacin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
IopromideIodixanol may decrease the excretion rate of Iopromide which could result in a higher serum level.Approved
IoversolIodixanol may decrease the excretion rate of Ioversol which could result in a higher serum level.Approved
KetamineKetamine may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
KetoprofenKetoprofen may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
LeuprolideLeuprolide may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
LisinoprilLisinopril may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
LorazepamLorazepam may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
MannitolMannitol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
Medroxyprogesterone acetateMedroxyprogesterone acetate may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
MetforminThe risk or severity of adverse effects can be increased when Iodixanol is combined with Metformin.Approved
MethylphenidateMethylphenidate may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
MetolazoneMetolazone may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
NeomycinNeomycin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
OseltamivirOseltamivir may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
ParoxetineParoxetine may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
PindololPindolol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
Potassium ChloridePotassium Chloride may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Withdrawn
PropranololPropranolol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
PyridoxinePyridoxine may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational, Nutraceutical, Vet Approved
SalbutamolSalbutamol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
Salmon CalcitoninSalmon Calcitonin may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Investigational
Sodium aurothiomalateIodixanol may decrease the excretion rate of Sodium aurothiomalate which could result in a higher serum level.Approved, Investigational
SpironolactoneSpironolactone may increase the excretion rate of Iodixanol which could result in a lower serum level and potentially a reduction in efficacy.Approved
SucralfateSucralfate may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
TerbutalineTerbutaline may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
Testosterone cypionateIodixanol may decrease the excretion rate of Testosterone cypionate which could result in a higher serum level.Approved
Testosterone enanthateIodixanol may decrease the excretion rate of Testosterone enanthate which could result in a higher serum level.Approved
TimololTimolol may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
TrimebutineIodixanol may decrease the excretion rate of Trimebutine which could result in a higher serum level.Approved
TrimethoprimTrimethoprim may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved, Vet Approved
VerapamilVerapamil may decrease the excretion rate of Iodixanol which could result in a higher serum level.Approved
WarfarinIodixanol may decrease the excretion rate of Warfarin which could result in a higher serum level.Approved
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
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 Embolism (PE)1
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
4RecruitingOtherChronic Kidney Disease (CKD)1
4TerminatedDiagnosticChronic Renal Diseases1
4TerminatedDiagnosticCoronary Artery Disease / Diabetes Mellitus (DM) / Impaired Renal Function1
4TerminatedDiagnosticDiabetes Mellitus (DM) / Impaired Renal Function1
4TerminatedDiagnosticDiabetes Mellitus (DM) / Renal Insufficiency,Chronic1
4TerminatedOtherImpaired Renal Function1
4Unknown StatusPreventionChronic Renal Failure (CRF)1
Not AvailableActive Not RecruitingPreventionCardio-Renal Syndrome1
Not AvailableCompletedDiagnosticAbdominal Aortic Aneurysms (AAA)1
Not AvailableCompletedPreventionCardio-Renal Syndrome1
Not AvailableNot Yet RecruitingNot 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
USRE36418No1994-07-122011-07-12Us

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
Polarizability111.45 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
show 10 more
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 September 17, 2018 20:53