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Metaiodobenzylguanidine

Synopsis, Chemistry

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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

Metaiodobenzylguanidine

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 Formula	C₈H₁₀IN₃
Molecular Weight	275.09 g/mol
XLogP3	1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	274.99194 g/mol
Monoisotopic Mass	274.99194 g/mol
Topological Polar Surface Area	64.4 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	166
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.