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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:32:40 UTC
HMDB IDHMDB15379
Secondary Accession NumbersNone
Metabolite Identification
Common NameIodixanol
DescriptionIodixanol is only found in individuals that have used or taken this drug. It 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.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.
Structure
Thumb
Synonyms
ValueSource
5,5'-((2-Hydroxytrimethylene)bis(acetylimino))bis(N,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)ChEBI
IodixanolumChEBI
IndixanolHMDB
Chemical FormulaC35H44I6N6O15
Average Molecular Weight1550.1819
Monoisotopic Molecular Weight1549.713275288
IUPAC Name5-{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
Traditional Nameiodixanol
CAS Registry Number92339-11-2
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
InChI Identifier
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)
InChI KeyInChIKey=NBQNWMBBSKPBAY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids and derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids and derivatives
Alternative Parents
Substituents
  • Halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Acetanilide
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Aminobenzamide
  • Benzoyl
  • Iodobenzene
  • Halobenzene
  • Aryl iodide
  • Aryl halide
  • Acetamide
  • Vinylogous halide
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-diol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Contrast Media
Application
  • Pharmaceutical
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.85e-01 g/LNot Available
LogP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01249
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01249
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01249
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3593
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIodixanol
NuGOwiki LinkHMDB15379
Metagene LinkHMDB15379
METLIN IDNot Available
PubChem Compound3724
PDB IDNot Available
ChEBI ID31705
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [8957160 ]
  2. McCullough PA: Renal safety of iodixanol. Expert Rev Cardiovasc Ther. 2006 Sep;4(5):655-61. [17081087 ]