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    Iohexol

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    Also known as: 66108-95-0, Omnipaque, Nycodenz, Exypaque, Iohexolum, Omnipaque 240
    Molecular Formula
    C19H26I3N3O9
    Molecular Weight
    821.1  g/mol
    InChI Key
    NTHXOOBQLCIOLC-UHFFFAOYSA-N
    FDA UNII
    4419T9MX03
    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.
    Iohexol is a Radiographic Contrast Agent. The mechanism of action of iohexol is as a X-Ray Contrast Activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[acetyl(2,3-dihydroxypropyl)amino]-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
    2.1.2 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)
    2.1.3 InChI Key
    NTHXOOBQLCIOLC-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(=O)N(CC(CO)O)C1=C(C(=C(C(=C1I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I
    2.2 Other Identifiers
    2.2.1 UNII
    4419T9MX03
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Compound 545

    2. Exypaque

    3. Iohexol 350

    4. Nycodenz

    5. Omnipaque

    2.3.2 Depositor-Supplied Synonyms

    1. 66108-95-0

    2. Omnipaque

    3. Nycodenz

    4. Exypaque

    5. Iohexolum

    6. Omnipaque 240

    7. Omnipaque 70

    8. Omnipaque 140

    9. Omnipaque 180

    10. Omnipaque 210

    11. Omnipaque 300

    12. Omnipaque 350

    13. Win 39424

    14. Oraltag

    15. Win-39424

    16. Chebi:31709

    17. N,n'-bis(2,3-dihydroxypropyl)-5-(n-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide

    18. 5-[acetyl(2,3-dihydroxypropyl)amino]-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

    19. 5-[acetyl(2,3-dihydroxypropyl)amino]-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

    20. N1,n3-bis(2,3-dihydroxypropyl)-5-(n-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide

    21. 4419t9mx03

    22. Nsc-759636

    23. Ncgc00166000-01

    24. Dsstox_cid_3157

    25. 5-(n-2,3-dihydroxypropylacetamido)-2,4,6-triiodo-n,n'-bis(2,3-dihydroxypropyl)isophthalamide

    26. Dsstox_rid_76895

    27. Dsstox_gsid_23157

    28. 1,3-benzenedicarboxamide, 5-(acetyl(2,3-dihydroxypropyl)amino)-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

    29. Histodenz

    30. Iohexolum [inn-latin]

    31. 1,3-benzenedicarboxamide, 5-[acetyl(2,3-dihydroxypropyl)amino]-n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

    32. 5-[acetyl(2,3-dihydroxypropyl)amino]-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

    33. 5-[n-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodo-n,n'-bis(2,3-dihydroxypropyl)isophthalamide

    34. Smr000857075

    35. Einecs 266-164-2

    36. Brn 2406632

    37. Unii-4419t9mx03

    38. Omnipaque (tn)

    39. 1,3-benzenedicarboxamide, 5-[acetyl(2,3-dihydroxypropyl)amino]-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

    40. N,n'-bis(2,3-dihydroxypropyl)-5-[n-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodoisophthalamide

    41. Prestwick_802

    42. Cas-66108-95-0

    43. Iohexol [usan:usp:inn:ban:jan]

    44. Iohexol [vandf]

    45. Iohexol [usan]

    46. Iohexol [inn]

    47. Iohexol [jan]

    48. Iohexol [mi]

    49. Iohexol [mart.]

    50. Prestwick0_000512

    51. Prestwick1_000512

    52. Prestwick2_000512

    53. Prestwick3_000512

    54. Iohexol [usp-rs]

    55. Iohexol [who-dd]

    56. Iohexol [who-ip]

    57. Nycodenz;omnipaque;exypaque

    58. Ec 266-164-2

    59. Iohexol, Analytical Standard

    60. Schembl26501

    61. Bspbio_000463

    62. Mls001332585

    63. Mls001332586

    64. Mls002153854

    65. Iohexol (jp17/usp/inn)

    66. Iohexol [ep Impurity]

    67. Iohexol [orange Book]

    68. Spbio_002384

    69. Iohexol [ep Monograph]

    70. Bpbio1_000511

    71. Iohexol [usp Monograph]

    72. Chembl1200455

    73. Dtxsid6023157

    74. Bcbcmap01_000051

    75. Iohexolum [who-ip Latin]

    76. Hms1569h05

    77. Hms2096h05

    78. Hms2235d07

    79. Hms3369o04

    80. Hms3713h05

    81. Albb-028959

    82. Amy21804

    83. Bcp31800

    84. Hy-b0594

    85. Tox21_112286

    86. Bdbm50247977

    87. Iohexol (mixture Of Isomers)

    88. Mfcd00077732

    89. S4531

    90. Akos015895399

    91. Tox21_112286_1

    92. Ac-1934

    93. Ccg-220512

    94. Db01362

    95. Nsc 759636

    96. Smp1_000152

    97. Ncgc00166000-02

    98. Ncgc00166000-04

    99. As-12699

    100. Ft-0627276

    101. I0903

    102. D01817

    103. D91214

    104. Histodenz(tm), Nonionic Density Gradient Medium

    105. 108i950

    106. A835339

    107. Q410683

    108. Sr-01000838892

    109. Sr-01000838892-2

    110. Iohexol, European Pharmacopoeia (ep) Reference Standard

    111. Iohexol, United States Pharmacopeia (usp) Reference Standard

    112. 5-(n-dhp-acetamido)-2,4,6-triiodo-n,n'-b Is-dhp-isophthalami

    113. Iohexol, Pharmaceutical Secondary Standard; Certified Reference Material

    114. Iohexol For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    115. 1,3-benzenedicarboxamide, 5-(acetyl(2,3-dihydroxypropyl)amino)-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo

    116. 1-n,3-n-bis(2,3-dihydroxypropyl)-5-[n-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide

    117. 5-[acetyl(2,3-dihydroxypropyl)amino]-n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

    118. N1,n3-bis(2,3-dihydroxypropyl)-5-[n-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide

    119. N1,n3-bis[2,3-bis(oxidanyl)propyl]-5-[2,3-bis(oxidanyl)propyl-ethanoyl-amino]-2,4,6-tris(iodanyl)benzene-1,3-dicarboxamide

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 821.1 g/mol
    Molecular Formula C19H26I3N3O9
    XLogP3-3
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count12
    Exact Mass820.8803 g/mol
    Monoisotopic Mass820.8803 g/mol
    Topological Polar Surface Area200 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity653
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count3
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameOmnipaque 180
    PubMed HealthIohexol (Injection)
    Drug ClassesRadiological Non-Ionic Contrast Media
    Active IngredientIohexol
    Dosage FormSolution
    RouteInjection, oral, rectal
    Strength38.8%
    Market StatusPrescription
    CompanyGe Healthcare

    2 of 4  
    Drug NameOmnipaque 240
    Active IngredientIohexol
    Dosage FormSolution
    RouteInjection, oral, rectal
    Strength51.8%
    Market StatusPrescription
    CompanyGe Healthcare

    3 of 4  
    Drug NameOmnipaque 180
    PubMed HealthIohexol (Injection)
    Drug ClassesRadiological Non-Ionic Contrast Media
    Active IngredientIohexol
    Dosage FormSolution
    RouteInjection, oral, rectal
    Strength38.8%
    Market StatusPrescription
    CompanyGe Healthcare

    4 of 4  
    Drug NameOmnipaque 240
    Active IngredientIohexol
    Dosage FormSolution
    RouteInjection, oral, rectal
    Strength51.8%
    Market StatusPrescription
    CompanyGe Healthcare

    4.2 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Contrast Media

    Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    IOHEXOL
    5.3.2 FDA UNII
    4419T9MX03
    5.3.3 Pharmacological Classes
    X-Ray Contrast Activity [MoA]; Radiographic Contrast Agent [EPC]
    5.4 ATC Code

    V08AB02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    V - Various

    V08 - Contrast media

    V08A - X-ray contrast media, iodinated

    V08AB - Watersoluble, nephrotropic, low osmolar x-ray contrast media

    V08AB02 - Iohexol

    5.5 Absorption, Distribution and Excretion

    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.

    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.

    Volume of Distribution

    350-849 mL/kg

    Clearance

    109 mL/min [Adult patients receiving 16-18 ml of iohexol (180 mgI/mL) by lumbar intrathecal injection]

    5.6 Biological Half-Life

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

    5.7 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.