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Also known as: 28179-44-4, Acido ioxitalamico, Acide ioxitalamique, Acidum ioxitalamicum, Iooxitalamic acid, Ag 58107

Molecular Formula

C₁₂H₁₁I₃N₂O₅

Molecular Weight

643.94 g/mol

InChI Key

OLAOYPRJVHUHCF-UHFFFAOYSA-N

FDA UNII

967RDI7Z6K

Ioxitalamate is an ionic iodinated contrast medium. It is a first-generation contrast media formed by an ionic monomer with a high osmolarity of 1500-1800 mOsm/kg. Ioxitalamic acid in the salt forms of sodium and meglumine was developed by Liebel-Flarshem Canada Inc and approved by Health Canada in 1995. Until the last review in 2015, this drug is still available in the market.

1 2D Structure

Ioxitalamic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-acetamido-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid

2.1.2 InChI

InChI=1S/C12H11I3N2O5/c1-4(19)17-10-8(14)5(11(20)16-2-3-18)7(13)6(9(10)15)12(21)22/h18H,2-3H2,1H3,(H,16,20)(H,17,19)(H,21,22)

2.1.3 InChI Key

OLAOYPRJVHUHCF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

967RDI7Z6K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-acetamido-n-(2- Hydroxyethyl)-2,4,6-triiodoisophthalamic Acid

2. Agelix

3. Ioxitalamic Acid, Sodium Salt

4. Ioxithalamate

5. Sodium Ioxithalamate

6. Telebrix

7. Telebrix 38

8. Vasobrix

2.3.2 Depositor-Supplied Synonyms

1. 28179-44-4

2. Acido Ioxitalamico

3. Acide Ioxitalamique

4. Acidum Ioxitalamicum

5. Iooxitalamic Acid

6. Ag 58107

7. Ioxithalamic Acid

8. 3-acetamido-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic Acid

9. Telebrix

10. 3-acetamido-5-((2-hydroxyethyl)carbamoyl)-2,4,6-triiodobenzoic Acid

11. Ioxitalamic Acid Sodium Salt

12. 967rdi7z6k

13. Chebi:83517

14. Ag-58107

15. Ioxitalamic Acid (inn)

16. 3-(acetamido)-5-[[(2-hydroxyethyl)amino]carbonyl]-2,4,6-triiodo-benzoic Acid

17. Ioxitalamic Acid [inn]

18. Vasobrix

19. 5-acetamido-n-(2-hydroxyethyl)-2,4,6-triiodoisophthalamic Acid

20. 3-(acetylamino)-5-[[(2-hydroxyethyl)amino]carbonyl]-2,4,6-triiodobenzoic Acid

21. 3-(acetylamino)-5-{[(2-hydroxyethyl)amino]carbonyl}-2,4,6-triiodobenzoic Acid

22. Acido Iossitalamico

23. Acidum Joxitalamicum

24. Ioxitalamic Acid [inn:dcf]

25. Ioxitalamicacid

26. Acido Iossitalamico [dcit]

27. Unii-967rdi7z6k

28. 3-(acetylamino)-5-(((2-hydroxyethyl)amino)carbonyl)-2,4,6-triiodobenzoic Acid

29. Acide Ioxitalamique [inn-french]

30. Acido Ioxitalamico [inn-spanish]

31. Acidum Ioxitalamicum [inn-latin]

32. Einecs 248-887-5

33. Mls006010884

34. Schembl455411

35. Acido Ioxitalamico;ioxitalamate

36. Chembl2107239

37. Dtxsid60182457

38. Ioxitalamic Acid [mart.]

39. Ioxitalamic Acid [who-dd]

40. Act03777

41. Amy24792

42. Bcp34384

43. Zinc4216615

44. Mfcd00867942

45. Sodium 3-acetamido-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoate

46. Db13444

47. Smr004701800

48. Ft-0659353

49. D07418

50. F20665

51. 179i444

52. Sr-01000945067

53. Q3604532

54. Sr-01000945067-1

55. W-110718

56. 5-acetamido-2,4,6-triiodo-n-(2-hydroxyethyl)-isophthalamic Acid

57. 3-(acetylamino)-5-[(2-hydroxyethyl)carbamoyl]-2,4,6-triiodobenzoic Acid

58. 3-acetamido-2,4,6-triiodo-(n-beta-hydroxyethyl)isophthalic Acid Monoamide

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₁I₃N₂O₅
Molecular Weight	643.94 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	643.7802 g/mol
Monoisotopic Mass	643.7802 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	451
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

Ioxitalamate in both of its available forms is indicated for exploration of the digestive tract by tomodensitometry or by regular gastroduodenal radiography. Its use is restrained to the cases in which the administration of barium sulfate is not recommended or contraindicated. The intravascular administration of ioxitalamate is contraindicated as it may present significant side effects.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ioxitalamate presents a very large osmolality which is related to the presence of renal toxicity, vasodilatation, bradycardia and pulmonary hypertension. This large osmolality allows ioxitalamate to move slowly in the bowel allowing for analysis for later follow excretion in the feces.

5.2 MeSH Pharmacological Classification

Contrast Media

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

5.3 ATC Code

V08AA05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

V - Various

V08 - Contrast media

V08A - X-ray contrast media, iodinated

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

V08AA05 - Ioxitalamic acid

5.4 Absorption, Distribution and Excretion

Absorption

When administered ioxitalamate is not absorbed in the GI tract. In the case of presence of an intestinal perforation, ioxitalamate is completely absorbed. When administered intravascularly, ioxitalamate is rapidly distributed in the interstitial space and intravascular compartment.

Route of Elimination

As ioxitalamate is not absorbed in the normal intestine, the elimination route of this compound is entirely performed by the feces. When absorbed due to the presence of an intestinal perforation, ioxitalamate presents a rapid renal elimination. when ioxitalamate is administered intravascularly, it is eliminated unchanged mainly via renal excretion through glomerular filtration without reabsorption or tubular secretion. In the cases of renal failure, the elimination is mainly performed in the biliary, salivary, sudoral and colic route.

Volume of Distribution

The volume of distribution of ioxitalamate is 194 ml/kg.

Clearance

The total clearance rate of ioxitalamate is 120 ml/min.

5.5 Metabolism/Metabolites

The rapid clearance suggests that ioxitalamate is not metabolized in the body.

5.6 Biological Half-Life

The elimination half-life of ioxitalamate is 1.1 hours.

5.7 Mechanism of Action

Ioxitalamate acts as a bowel opacifier which facilitates the interpretation of the anatomy and differentiation of bowel loops from soft tissue masses.

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