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

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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

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 Formula	C₁₆H₂₂I₂N₆O₄S
Molecular Weight	648.3 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	647.95127 g/mol
Monoisotopic Mass	647.95127 g/mol
Topological Polar Surface Area	212 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	247
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	3

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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