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Chemistry

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Also known as: 87862-25-7, Mibg, Iobenguane sulphate, M-iodobenzylguanidine hemisulfate, M-iodobenzyl guanidine sulfate, 1-(3-iodobenzyl)guanidine hemisulfate
Molecular Formula
C16H22I2N6O4S
Molecular Weight
648.3  g/mol
InChI Key
XNACDNPGABUBFR-UHFFFAOYSA-N
FDA UNII
S8I0922465

Iobenguane
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

Iobenguane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(3-iodophenyl)methyl]guanidine;sulfuric acid
2.1.2 InChI
InChI=1S/2C8H10IN3.H2O4S/c2*9-7-3-1-2-6(4-7)5-12-8(10)11;1-5(2,3)4/h2*1-4H,5H2,(H4,10,11,12);(H2,1,2,3,4)
2.1.3 InChI Key
XNACDNPGABUBFR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC(=C1)I)CN=C(N)N.C1=CC(=CC(=C1)I)CN=C(N)N.OS(=O)(=O)O
2.2 Other Identifiers
2.2.1 UNII
S8I0922465
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

11. Iobenguane (131i)

12. M Iodobenzylguanidine

13. M-iodobenzylguanidine

14. Meta Iodobenzylguanidine

15. Meta-iodobenzylguanidine

16. Mibg

2.3.2 Depositor-Supplied Synonyms

1. 87862-25-7

2. Mibg

3. Iobenguane Sulphate

4. M-iodobenzylguanidine Hemisulfate

5. M-iodobenzyl Guanidine Sulfate

6. 1-(3-iodobenzyl)guanidine Hemisulfate

7. Mibg (sulfate)

8. 3-iodobenzyl-guanidine Sulfate

9. M-iodobenzyl Guanidine Sulphate

10. 3-iodobenzyl-guanidine Sulphate

11. Iobenguane (sulfate)

12. Guanidine, N-((3-iodophenyl)methyl)-, Sulfate (2:1)

13. M-idobenzyl Guanidine Sulfate [vandf]

14. Guanidine, [(3-iodophenyl)methyl]-, Sulfate (2:1)

15. M-iodobenzylguanidine Hemisulfate Salt

16. Mibg Hemisulfate

17. Ncgc00094011-01

18. S8i0922465

19. Dsstox_cid_25773

20. Dsstox_rid_81115

21. Dsstox_gsid_45773

22. 3-iodobenzylguanidine Hemisulfate

23. Cas-87862-25-7

24. Ncgc00015572-04

25. Eu-0100644

26. 1-(3-iodobenzyl)guanidine Hcl

27. Chembl1374843

28. 3-iodobenzylguanidine Hemisulphate

29. 3-iodobenzyl-guanidine Hemisulfate

30. Hms3262a09

31. Unii-s8i0922465

32. Tox21_111237

33. Tox21_113518

34. Tox21_500644

35. 1-(3-iodobenzyl)guanidinehemisulfate

36. Akos015996512

37. Meta-iodobenzylguanidine Sulfate

38. Ccg-221948

39. Lp00644

40. Ncgc00261329-01

41. Bs-45793

42. E74924

43. I 9890

44. 2-[(3-iodophenyl)methyl]guanidine; Sulfuric Acid

45. A839961

46. 2-[(3-iodanylphenyl)methyl]guanidine; Sulfuric Acid

47. Q27289056

48. M-iodobenzylguanidine Hemisulfate Salt, >=98% (hplc And Tlc)

49. 3-iodobenzyl-guanidine Hemisulfate 103346-16-3 80663-96-3

50. Iobenguane Sulfate, European Pharmacopoeia (ep) Reference Standard

51. 80663-96-3

2.4 Create Date
2006-12-01
3 Chemical and Physical Properties
Molecular Weight 648.3 g/mol
Molecular Formula C16H22I2N6O4S
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass647.95127 g/mol
Monoisotopic Mass647.95127 g/mol
Topological Polar Surface Area212 Ų
Heavy Atom Count29
Formal Charge0
Complexity247
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antineoplastic Agents

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


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.)


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.)


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