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2D Structure
Also known as: 107793-72-6, Oxilan, Ioxitol, Oxilan-300, Nsc-760056, A4yj7j11tg
Molecular Formula
C18H24I3N3O8
Molecular Weight
791.1  g/mol
InChI Key
UUMLTINZBQPNGF-UHFFFAOYSA-N
FDA UNII
A4YJ7J11TG

Ioxilan is a tri-iodinated diagnostic contrast agent. Intravascular injection results in opacification of vessels in the path of flow of the contrast medium, permitting radiographic visualization of the internal structures of the human body until significant hemodilution occurs.
Ioxilan is a Radiographic Contrast Agent. The mechanism of action of ioxilan is as a X-Ray Contrast Activity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[acetyl(2,3-dihydroxypropyl)amino]-3-N-(2,3-dihydroxypropyl)-1-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
2.1.2 InChI
InChI=1S/C18H24I3N3O8/c1-8(28)24(5-10(30)7-27)16-14(20)11(17(31)22-2-3-25)13(19)12(15(16)21)18(32)23-4-9(29)6-26/h9-10,25-27,29-30H,2-7H2,1H3,(H,22,31)(H,23,32)
2.1.3 InChI Key
UUMLTINZBQPNGF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)N(CC(CO)O)C1=C(C(=C(C(=C1I)C(=O)NCC(CO)O)I)C(=O)NCCO)I
2.2 Other Identifiers
2.2.1 UNII
A4YJ7J11TG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-(n-2,3-dihydroxypropylacetamido)-2,4,6-triiodo-n-(2-hydroxyethyl)-n'-(2,3-dihydroxypropyl)isophthalamide

2. Oxilan

2.3.2 Depositor-Supplied Synonyms

1. 107793-72-6

2. Oxilan

3. Ioxitol

4. Oxilan-300

5. Nsc-760056

6. A4yj7j11tg

7. 5-[acetyl(2,3-dihydroxypropyl)amino]-3-n-(2,3-dihydroxypropyl)-1-n-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

8. N-(2,3-dihydroxypropyl)-5-(n-(2,3-dihydroxypropyl)acetamido)-n'-(2-hydroxyethyl)-2,4,6-triiodoisophthalamide

9. Ncgc00182070-02

10. Dsstox_cid_28643

11. Dsstox_rid_82913

12. Dsstox_gsid_48717

13. Ioxilane

14. Ioxilanum

15. 1,3-benzenedicarboxamide, 5-(acetyl(2,3-dihydroxypropyl)amino)-n-(2,3-dihydroxypropyl)-n'-(2-hydroxyethyl)-2,4,6-triiodo-

16. Cas-107793-72-6

17. Oxilan-350

18. Ioxilane [inn-french]

19. Ioxilanum [inn-latin]

20. Unii-a4yj7j11tg

21. Ioxilan [usan:usp:inn]

22. Imagenil

23. Loxilan

24. Ccris 6727

25. 1,3-benzenedicarboxamide, 5-(acetyl(2,3-dihydroxypropyl)amino)-n1-(2,3-dihydroxypropyl)-n3-(2-hydroxyethyl)-2,4,6-triiodo-

26. 1,3-benzenedicarboxamide, 5-[acetyl(2,3-dihydroxypropyl)amino]-n1-(2,3-dihydroxypropyl)-n3-(2-hydroxyethyl)-2,4,6-triiodo-

27. Ioxilan(400 Mg)

28. Ioxilan [vandf]

29. Loxilan [vandf]

30. Ioxilan [usan]

31. Ioxilan [inn]

32. Ioxilan [jan]

33. Ioxilan [mi]

34. Oxilan-300 (tn)

35. Ioxilan [mart.]

36. Ioxilan [usp-rs]

37. Ioxilan [who-dd]

38. Ioxilan (jan/usp/inn)

39. Schembl25634

40. Ioxilan [orange Book]

41. Ioxilan (400 Mg)

42. Ioxilan [usp Impurity]

43. Ioxilan [usp Monograph]

44. Chembl1201075

45. Dtxsid0048717

46. Chebi:135884

47. Hms3264d15

48. Moli000985

49. Pharmakon1600-01503838

50. Tox21_113127

51. Nsc760056

52. Akos016014026

53. Tox21_113127_1

54. Ccg-213210

55. Db09135

56. Nsc 760056

57. Ncgc00182070-03

58. Hy-109513

59. Cs-0031230

60. Ft-0627286

61. D02161

62. Ab01563289_01

63. Sr-01000883963

64. J-002011

65. Q6064819

66. Sr-01000883963-1

67. 3-(3-methyl-4-oxo-thiazolidin-2-ylideneamino)-benzoicacid

68. 5-(n-2,3-dihydroxypropylacetamido)-2,4,6-triiodo-n-(2-hydroxyethyl)-n -(2,3-dihydroxypropyl)-isophthalamide

69. 5-[acetyl(2,3-dihydroxypropyl)amino]-n-(2,3-dihydroxypropyl)-n'-(2-hydroxyethyl)-2,4,6-triiodoisophthalamide

70. N-(2,3-dihdroxypropyl)-n -(2-hydroxyethyl)-5-[n-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodoiosphthalamide

71. N-(2,3-dihydroxypropyl)-n'-(2- Hydroxyethyl)-5-[n-(2,3-dihydroxypropyl) Acetamido]-2,4,6-triiodoisophthal-amide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 791.1 g/mol
Molecular Formula C18H24I3N3O8
XLogP3-2.4
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count8
Rotatable Bond Count11
Exact Mass790.8698 g/mol
Monoisotopic Mass790.8698 g/mol
Topological Polar Surface Area180 Ų
Heavy Atom Count32
Formal Charge0
Complexity647
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameOxilan-300
Active IngredientIoxilan
Dosage FormInjectable
RouteInjection
Strength62%
Market StatusPrescription
CompanyGuerbet

2 of 4  
Drug NameOxilan-350
Active IngredientIoxilan
Dosage FormInjectable
RouteInjection
Strength73%
Market StatusPrescription
CompanyGuerbet

3 of 4  
Drug NameOxilan-300
Active IngredientIoxilan
Dosage FormInjectable
RouteInjection
Strength62%
Market StatusPrescription
CompanyGuerbet

4 of 4  
Drug NameOxilan-350
Active IngredientIoxilan
Dosage FormInjectable
RouteInjection
Strength73%
Market StatusPrescription
CompanyGuerbet

4.2 Drug Indication

When administered intra-arterially, Ioxilan is indicated for the following diagnostic tests: cerebral arteriography (300 mgI/mL), coronary arteriography and left ventriculography (350 mgI/mL), visceral angiography(350 mgI/mL), aortography(350 mgI/mL), and peripheral arteriography(350 mgI/mL). When administered intravenously, Ioxilan is indicated for excretory urography and contrast enhanced computed tomographic (CECT) imaging of the head and body (300 and 350 mgI/mL).


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

As with other iodinated contrast agents the degree of contrast enhancement is directly related to the iodine content in the administered dose.


5.2 MeSH Pharmacological Classification

Contrast Media

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


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
IOXILAN
5.3.2 FDA UNII
A4YJ7J11TG
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - X-Ray Contrast Activity
5.4 ATC Code

V - Various

V08 - Contrast media

V08A - X-ray contrast media, iodinated

V08AB - Watersoluble, nephrotropic, low osmolar x-ray contrast media

V08AB12 - Ioxilan


5.5 Absorption, Distribution and Excretion

Absorption

Peak iodine plasma levels occur immediately following rapid intravenous injection. Iodine plasma levels fall rapidly within 5 to 10 minutes. This can be accounted for by the dilution in the vascular and extravascular fluid compartments.


Route of Elimination

The average amount of ioxilan excreted unchanged in urine at 24 hours represents 93.7% of the dose in young healthy subjects (21-27 years) after intravenous administration. This finding suggests that, compared to the renal excretion, biliary and/or gastrointestinal excretion are not important.


Volume of Distribution

Ioxilan is distributed mainly in the blood as suggested by the apparent volume of distribution (central compartment), 7.2 1.0 L in women and 10.0 2.4 L in men


Clearance

The total clearance values were 95.4 11.1 mLmin-1 and 101.0 14.7 mLmin-1 and the renal clearance values were 89.4 13.3 mLmin-1 and 94.9 16.6 mLmin-1 for women and men, respectively.


5.6 Metabolism/Metabolites

There is no evidence for metabolism.


5.7 Biological Half-Life

An initial fast distribution phase with a half-life of 13.1 4.2 minutes (women) or 23.5 15.3 minutes (men) was followed by an elimination phase with a half-life of 102.0 16.9 minutes (women) and 137 35.4 minutes (men).


5.8 Mechanism of Action

Intravascular injection results in opacification of vessels in the path of flow of the contrast medium, permitting radiographic visualization of the internal structures of the human body until significant hemodilution occurs.