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Iohexol

July 24, 2017
Common Name

Iohexol Description

Iohexol is only found in individuals that have used or taken this drug. It 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 reslit of low chemotoxicity and low osmolality. [PubChem]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 intravascliar administration, iohexol makes opaque those vessels in its path of flow, allowing visualization of the internal structures until significant hemodilution occurs. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source IohexolumChEBI N,N'-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamideChEBI Compound 545MeSH Iohexol 350MeSH OmnipaqueMeSH ExypaqueMeSH NycodenzMeSH

Chemical Formlia

C19H26I3N3O9 Average Molecliar Weight

821.1379 Monoisotopic Molecliar Weight

820.880309705 IUPAC Name

N1,N3-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide Traditional Name

iohexol CAS Registry Number

66108-95-0 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

InChI Identifier

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)

InChI Key

NTHXOOBQLCIOLC-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives 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
  • Organonitrogen compounds
  • Organoiodides
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • O-haloacetanilide
  • P-haloacetanilide
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Acetamide
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Alcohol
  • Organoiodide
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • organoiodine compound (CHEBI:31709 )
  • benzenedicarboxamide (CHEBI:31709 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Contrast Agents
  • Contrast Media

    • Application

  • Pharmaceutical

    • Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point174 – 180 °CNot Available Boiling PointNot AvailableNot Available Water Solubility7.96e-01 g/LNot Available LogP-3.05HANSCH,C & LEO,AJ (1985)

    Predicted Properties

    Property Value Source Water Solubility0.8 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0udi-0000000090-ec4e884f5d1e3e37a84fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0udi-0020002090-d8ff0c2813768e3cf012View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00dj-0009850000-7a1ca449a56d19c39ea8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0fk9-0009120000-a8c863a64d387cfd461aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0kmi-0496000000-bff588cc0e98918355e8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-05fu-0492000000-4a9469f17183d2f9f291View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0udi-0020003090-7423fd2df7e59f0f78eeView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0fka-0008951000-ea0d52cf6d356a7f3590View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0fk9-0029120000-e5ff4d33e064ff47ff49View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0kmi-0395000000-775d49075e4ad66be119View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-05i1-0492000000-1a8b12a2e372f5b00ca1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0udi-0000000090-262fc3f19d8442742408View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

    Not Available Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01362

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01362

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01362 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    3599 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Iohexol NuGOwiki Link

    HMDB15449 Metagene Link

    HMDB15449 METLIN ID

    Not Available PubChem Compound

    3730 PDB ID

    Not Available ChEBI ID

    31709

    Product: Sarpogrelate (hydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Shaw DD, Potts DG: Toxicology of iohexol. Invest Radiol. 1985 Jan-Feb;20(1 Suppl):S10-3. [PubMed:3882609 ]
    2. 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 ]

    PMID: 10614629

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