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Ioxilan

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2 FDF Dossiers, 2 FDA Orange Book

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2 FDA Orange Book

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2 Others

Synopsis

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Chemistry

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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

Ioxilan

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 Formula	C₁₈H₂₄I₃N₃O₈
Molecular Weight	791.1 g/mol
XLogP3	-2.4
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	11
Exact Mass	790.8698 g/mol
Monoisotopic Mass	790.8698 g/mol
Topological Polar Surface Area	180 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	647
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Oxilan-300
Active Ingredient	Ioxilan
Dosage Form	Injectable
Route	Injection
Strength	62%
Market Status	Prescription
Company	Guerbet

2 of 4
Drug Name	Oxilan-350
Active Ingredient	Ioxilan
Dosage Form	Injectable
Route	Injection
Strength	73%
Market Status	Prescription
Company	Guerbet

3 of 4
Drug Name	Oxilan-300
Active Ingredient	Ioxilan
Dosage Form	Injectable
Route	Injection
Strength	62%
Market Status	Prescription
Company	Guerbet

4 of 4
Drug Name	Oxilan-350
Active Ingredient	Ioxilan
Dosage Form	Injectable
Route	Injection
Strength	73%
Market Status	Prescription
Company	Guerbet

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.

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