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    Metaiodobenzylguanidine

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
    Xls

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    2D Structure
    Also known as: M-iodobenzylguanidine, 80663-95-2, 3-iodobenzylguanidine, Metaiodobenzylguanidine, Mibg, 2-[(3-iodophenyl)methyl]guanidine
    Molecular Formula
    C8H10IN3
    Molecular Weight
    275.09  g/mol
    InChI Key
    PDWUPXJEEYOOTR-UHFFFAOYSA-N
    FDA UNII
    35MRW7B4AD
    A guanidine analog with specific affinity for tissues of the sympathetic nervous system and related tumors. The radiolabeled forms are used as antineoplastic agents and radioactive imaging agents. (Merck Index, 12th ed) MIBG serves as a neuron-blocking agent which has a strong affinity for, and retention in, the adrenal medulla and also inhibits ADP-ribosyltransferase.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(3-iodophenyl)methyl]guanidine
    2.1.2 InChI
    InChI=1S/C8H10IN3/c9-7-3-1-2-6(4-7)5-12-8(10)11/h1-4H,5H2,(H4,10,11,12)
    2.1.3 InChI Key
    PDWUPXJEEYOOTR-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=CC(=C1)I)CN=C(N)N
    2.2 Other Identifiers
    2.2.1 UNII
    35MRW7B4AD
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3-iodo-(131i)benzyl)guanidine

    2. 123i Labeled 3-iodobenzylguanidine

    3. 125i Labeled 3-iodobenzylguanidine

    4. 3 Iodobenzylguanidine

    5. 3 Iodobenzylguanidine, 123i Labeled

    6. 3 Iodobenzylguanidine, 125i Labeled

    7. 3-iodobenzylguanidine

    8. 3-iodobenzylguanidine, 123i Labeled

    9. 3-iodobenzylguanidine, 125i Labeled

    10. Iobenguane (131i)

    11. M Iodobenzylguanidine

    12. M-iodobenzylguanidine

    13. Meta Iodobenzylguanidine

    14. Meta-iodobenzylguanidine

    15. Mibg

    2.3.2 Depositor-Supplied Synonyms

    1. M-iodobenzylguanidine

    2. 80663-95-2

    3. 3-iodobenzylguanidine

    4. Metaiodobenzylguanidine

    5. Mibg

    6. 2-[(3-iodophenyl)methyl]guanidine

    7. Iobenguane (127-i)

    8. Guanidine, ((3-iodophenyl)methyl)-

    9. 139755-80-9

    10. Guanidine,n-[(3-iodophenyl)methyl]-

    11. 1-(3-iodobenzyl)guanidine

    12. 2-(3-iodobenzyl)guanidine

    13. 35mrw7b4ad

    14. ((3-iodophenyl)methyl)guanidine

    15. Meta-iodobenzylguanidine

    16. (3-iodobenzyl)guanidine

    17. Ncgc00015572-04

    18. Unii-35mrw7b4ad

    19. Sr-01000075167

    20. Prestwick-07a11

    21. Starbld0001019

    22. Iobenguane [mi]

    23. Meta-iodobenzyl Guanidine

    24. Prestwick0_000490

    25. Prestwick1_000490

    26. Prestwick2_000490

    27. Prestwick3_000490

    28. Lopac-i-9890

    29. 2-m-iodo-benzyl Guanidine

    30. Iobenguane [vandf]

    31. Chembl818

    32. Lopac0_000644

    33. Bspbio_000359

    34. Schembl140591

    35. Spbio_002280

    36. Bpbio1_000395

    37. Dtxsid4048438

    38. Chebi:92769

    39. 1-[(3-iodophenyl)methyl]guanidine

    40. Zinc1538318

    41. Ccg-204731

    42. Db06704

    43. Sdccgsbi-0050624.p002

    44. Ncgc00015572-01

    45. Ncgc00015572-02

    46. Ncgc00015572-03

    47. Ncgc00015572-06

    48. Ncgc00015572-09

    49. Ncgc00162211-01

    50. Da-02654

    51. Q3154058

    52. Sr-01000075167-1

    53. Brd-k43860855-065-03-6

    2.4 Create Date
    2005-07-19
    3 Chemical and Physical Properties
    Molecular Weight 275.09 g/mol
    Molecular Formula C8H10IN3
    XLogP31
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count2
    Exact Mass274.99194 g/mol
    Monoisotopic Mass274.99194 g/mol
    Topological Polar Surface Area64.4 Ų
    Heavy Atom Count12
    Formal Charge0
    Complexity166
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Detection of primary and metastatic pheochromocytoma or neuroblastoma

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    AdreView is a diagnostic radiopharmaceutical which contains a small quantity of iobenguane that is not expected to produce a pharmacodynamic effect. Patients with renal insufficiency may experience increased radiation exposure and impaired imaging results.

    5.2 MeSH Pharmacological Classification

    Radiopharmaceuticals

    Compounds that are used in medicine as sources of radiation for radiotherapy and for diagnostic purposes. They have numerous uses in research and industry. (Martindale, The Extra Pharmacopoeia, 30th ed, p1161) (See all compounds classified as Radiopharmaceuticals.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    Iobenguane rapidly clears from the blood and is highly retained in adrenergic tissues.

    Route of Elimination

    Renally excreted unchanged (70%-90%) via glomerular filtration; Fecal (<1%)

    5.4 Metabolism/Metabolites

    Less than 10% of the dose is metabolized into m-iodohippuric acid (MIHA). However the mechanism in which this metabolite is produced is unknown.

    5.5 Biological Half-Life

    Physical half life = 13.2 hours

    5.6 Mechanism of Action

    Structure of iobenguane is similar to noradrenaline so it can be taken up by adrenergic tissue in the adrenal medulla, liver, heart, and spleen. Once taken up by noradrenaline transporters in the adrenergic nerve terminals, it is stored in the presynaptic storage vesicles. The radioactive iodine component is responsible for its imaging properties.