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Chemistry

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Also known as: Iothalamic acid, 2276-90-6, 3-acetamido-2,4,6-triiodo-5-(methylcarbamoyl)benzoic acid, 5-acetamido-2,4,6-triiodo-n-methylisophthalamic acid, Iotalamic acid [inn], Mi-216

Molecular Formula

C₁₁H₉I₃N₂O₄

Molecular Weight

613.91 g/mol

InChI Key

UXIGWFXRQKWHHA-UHFFFAOYSA-N

FDA UNII

16CHD79MIX

A contrast medium in diagnostic radiology with properties similar to those of diatrizoic acid. It is used primarily as its sodium and meglumine (IOTHALAMATE MEGLUMINE) salts.

Iothalamic acid is a Radiographic Contrast Agent. The mechanism of action of iothalamic acid is as a X-Ray Contrast Activity.

1 2D Structure

Iotalamic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-acetamido-2,4,6-triiodo-5-(methylcarbamoyl)benzoic acid

2.1.2 InChI

InChI=1S/C11H9I3N2O4/c1-3(17)16-9-7(13)4(10(18)15-2)6(12)5(8(9)14)11(19)20/h1-2H3,(H,15,18)(H,16,17)(H,19,20)

2.1.3 InChI Key

UXIGWFXRQKWHHA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)NC1=C(C(=C(C(=C1I)C(=O)O)I)C(=O)NC)I

2.2 Other Identifiers

2.2.1 UNII

16CHD79MIX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Iotalamic

2. Acid, Iothalamic

3. Acid, Methalamic

4. Angio Conray

5. Angio-conray

6. Angioconray

7. Conray 420

8. Iodothalamate

9. Iothalamate

10. Iothalamate, Sodium

11. Iothalamic Acid

12. Iothalamic Acid, Calcium (2:1) Salt

13. Iothalamic Acid, Monosilver (1+) Salt

14. Iothalamic Acid, Monosodium Salt

15. Iothalamic Acid, Monosodium Salt, Dimer

16. Lopamidol

17. Methalamic Acid

18. Sodium Iothalamate

2.3.2 Depositor-Supplied Synonyms

1. Iothalamic Acid

2. 2276-90-6

3. 3-acetamido-2,4,6-triiodo-5-(methylcarbamoyl)benzoic Acid

4. 5-acetamido-2,4,6-triiodo-n-methylisophthalamic Acid

5. Iotalamic Acid [inn]

6. Mi-216

7. Nsc-759891

8. 16chd79mix

9. 3-(acetylamino)-2,4,6-triiodo-5-[(methylamino)carbonyl]benzoic Acid

10. Acidum Jotalamicum

11. Acido Iotalamico

12. Iothalamic Acid [usan]

13. Acide Iotalamique

14. Acidum Iotalamicum

15. Acide Iotalamique [inn-french]

16. Acido Iotalamico [inn-spanish]

17. Acidum Iotalamicum [inn-latin]

18. Einecs 218-897-4

19. Mi 216

20. Unii-16chd79mix

21. Iothalamic Acid [usan:usp]

22. Iothalamic-acid-d3

23. Benzoic Acid, 3-(acetylamino)-2,4,6-triiodo-5-((methylamino)carbonyl)-

24. Iothalamic Acid (usp)

25. Ec 218-897-4

26. Iothalamate [vandf]

27. Schembl38419

28. Iotalamic Acid [jan]

29. Iothalamic Acid [mi]

30. Iotalamic Acid (jp17/inn)

31. Iothalamicacid(200mg)

32. Iotalamic Acid [mart.]

33. Chembl1201300

34. Dtxsid5023164

35. Iotalamic Acid [who-dd]

36. Schembl23630220

37. Chebi:31713

38. Iothalamic Acid [usp-rs]

39. Hms3264d13

40. Pharmakon1600-01503836

41. Bcp13316

42. Hy-b1053

43. Zinc3830961

44. Iotalamic Acid [ep Impurity]

45. Nsc759891

46. Akos025402283

47. Benzoic Acid,3-(acetylamino)-2,4,6-triiodo-5-[(methylamino)carbonyl]-

48. Ac-7611

49. Ccg-213208

50. Cs-4575

51. Db09133

52. Iothalamic Acid [usp Monograph]

53. Nsc 759891

54. Ncgc00183042-01

55. Ft-0740526

56. D01258

57. Ab01563288_01

58. 276i906

59. Sr-01000944232

60. Q-201246

61. Q6064129

62. Sr-01000944232-1

63. 5-acetylamino-2,4,6-triiodo-n-methyl-isophthalamic Acid

64. 1-deoxy-1-(methylamino)-d-glucitol 5-acetamido-2,4,6 Triiodo-n-methylisophthalamate

65. Benzoic Acid, 3-(acetylamino)-2,4,6-triiodo-5-((methylamino)carbonyl

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₉I₃N₂O₄
Molecular Weight	613.91 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	613.7696 g/mol
Monoisotopic Mass	613.7696 g/mol
Topological Polar Surface Area	95.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	421
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

Conray is indicated for use in excretory urography, cerebral angiography, peripheral arteriography, venography, arthrography, direct cholangiography, endoscopic retrograde cholangiopancreatography, contrast enhancement of computed tomographic brain images, cranial computerized angiotomography, intravenous digital subtraction angiography and arterial digital subtraction angiography. Conray may also be used for enhancement of computed tomographic scans performed for detection and evaluation of lesions in the liver, pancreas, kidneys, abdominal aorta, mediastinum, abdominal cavity and retroperitoneal space.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Contrast Media

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

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

IOTHALAMIC ACID

5.2.2 FDA UNII

16CHD79MIX

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - X-Ray Contrast Activity

5.3 ATC Code

V - Various

V08 - Contrast media

V08A - X-ray contrast media, iodinated

V08AA - Watersoluble, nephrotropic, high osmolar x-ray contrast media

V08AA04 - Iotalamic acid

5.4 Absorption, Distribution and Excretion

Absorption

Renal accumulation is sufficiently rapid that maximum radiographic density in the calyces and pelves occurs, in most instances, about 3 to 8 minutes after injection. In patients with impaired renal function, diagnostic opacification frequently is achieved only after prolonged periods.

Route of Elimination

Following intravascular injection, Conray is rapidly transported through the circulatory system to the kidneys and is excreted unchanged in the urine by glomerular filtration. The liver and small intestine provide the major alternate route of excretion. In patients with severe renal impairment, the excretion of this contrast medium through the gallbladder and into the small intestine sharply increases.

5.5 Biological Half-Life

In patients with normal renal function, the alpha and beta half-lives of Conray were approximately 10 and 90 minutes, respectively.

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