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Chemistry

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Also known as: 87771-40-2, Optiray, Mp-328, 1,3-benzenedicarboxamide, n,n'-bis(2,3-dihydroxypropyl)-5-((hydroxyacetyl)(2-hydroxyethyl)amino)-2,4,6-triiodo-, Mp 328, Loversol

Molecular Formula

C₁₈H₂₄I₃N₃O₉

Molecular Weight

807.1 g/mol

InChI Key

AMDBBAQNWSUWGN-UHFFFAOYSA-N

FDA UNII

N3RIB7X24K

Ioversol is a sterile, nonpyrogenic, aqueous solution intended for intravascular administration as a diagnostic radiocontrast agent. Ioversol is available in various concentrations, ranging from 240 to 350 milligrams of iodine per milliliter.

Ioversol is a Radiographic Contrast Agent. The mechanism of action of ioversol is as a X-Ray Contrast Activity.

1 2D Structure

Ioversol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-N,3-N-bis(2,3-dihydroxypropyl)-5-[(2-hydroxyacetyl)-(2-hydroxyethyl)amino]-2,4,6-triiodobenzene-1,3-dicarboxamide

2.1.2 InChI

InChI=1S/C18H24I3N3O9/c19-13-11(17(32)22-3-8(29)5-26)14(20)16(24(1-2-25)10(31)7-28)15(21)12(13)18(33)23-4-9(30)6-27/h8-9,25-30H,1-7H2,(H,22,32)(H,23,33)

2.1.3 InChI Key

AMDBBAQNWSUWGN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(CO)N(C1=C(C(=C(C(=C1I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I)C(=O)CO

2.2 Other Identifiers

2.2.1 UNII

N3RIB7X24K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Optiray

2. Optiray 300

3. Optiray 320

2.3.2 Depositor-Supplied Synonyms

1. 87771-40-2

2. Optiray

3. Mp-328

4. 1,3-benzenedicarboxamide, N,n'-bis(2,3-dihydroxypropyl)-5-((hydroxyacetyl)(2-hydroxyethyl)amino)-2,4,6-triiodo-

5. Mp 328

6. Loversol

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

8. N3rib7x24k

9. Optiray 320

10. N,n'-bis(2,3-dihydroxypropyl)-5-(n-(2-hydroxyethyl)glycolamido)-2,4,6-triiodoisophthalamide

11. Dsstox_cid_25521

12. Dsstox_rid_80927

13. Dsstox_gsid_45521

14. Ioversolum [latin]

15. Optiray 160

16. Optiray 240

17. Optiray 300

18. Optiray 350

19. Ioversolum

20. Unii-n3rib7x24k

21. Brn 7155654

22. Ioversol [usan:usp:inn:ban]

23. Ncgc00016956-01

24. Optiray (tn)

25. Cas-87771-40-2

26. Ioversol [usan]

27. Ioversol [inn]

28. Ioversol [jan]

29. Ioversol [mi]

30. Ioversol [vandf]

31. Prestwick0_000878

32. Prestwick1_000878

33. Prestwick2_000878

34. Prestwick3_000878

35. Ioversol [mart.]

36. Ioversol [usp-rs]

37. Ioversol [who-dd]

38. Ioversol (jan/usp/inn)

39. Schembl24711

40. Bspbio_000955

41. Spbio_002876

42. Ioversol [orange Book]

43. Bpbio1_001051

44. Chembl1200614

45. Dtxsid2045521

46. Ioversol [usp Monograph]

47. Chebi:31717

48. Hms1570p17

49. Hms2097p17

50. Hms3714p17

51. Pharmakon1600-01503837

52. Bcp11109

53. Hy-b1410

54. Tox21_110709

55. Ac-536

56. Mp-328mp-328

57. Nsc760064

58. S5013

59. Akos015896385

60. Tox21_110709_1

61. Ccg-213209

62. Cs-7483

63. Db09134

64. Nsc-760064

65. Ncgc00179364-01

66. Ncgc00179364-03

67. 8771-40-2

68. As-12851

69. Ab00513943

70. Ft-0627284

71. D01555

72. Ab00513943_02

73. 771i402

74. Sr-01000872680

75. Q-201247

76. Q6064187

77. Sr-01000872680-1

78. Brd-a65818372-001-01-2

79. N,n'-bis (2,3-dihydroxypropyl)-5-[n-(2-hydroxyethyl) -glycolamido] -2,4,6-triiodoisophthalamide

80. N1,n3-bis(2,3-dihydroxypropyl)-5-(2-hydroxy-n-(2-hydroxyethyl)acetamido)-2,4,6-triiodoisophthalamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₄I₃N₃O₉
Molecular Weight	807.1 g/mol
XLogP3	-3
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	12
Exact Mass	806.8647 g/mol
Monoisotopic Mass	806.8647 g/mol
Topological Polar Surface Area	200 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	623
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 8
Drug Name	Optiray 240
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	51%
Market Status	Prescription
Company	Mallinckrodt

2 of 8
Drug Name	Optiray 300
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	64%
Market Status	Prescription
Company	Mallinckrodt

3 of 8
Drug Name	Optiray 320
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	68%
Market Status	Prescription
Company	Mallinckrodt

4 of 8
Drug Name	Optiray 350
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	74%
Market Status	Prescription
Company	Mallinckrodt

5 of 8
Drug Name	Optiray 240
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	51%
Market Status	Prescription
Company	Mallinckrodt

6 of 8
Drug Name	Optiray 300
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	64%
Market Status	Prescription
Company	Mallinckrodt

7 of 8
Drug Name	Optiray 320
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	68%
Market Status	Prescription
Company	Mallinckrodt

8 of 8
Drug Name	Optiray 350
Drug Label	Optiray (ioversol injection) formulations are sterile, nonpyrogenic, aqueous solutions intended for intravascular administration as diagnostic radiopaque media. Ioversol is designated chemically as N,N'-Bis (2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)
Active Ingredient	Ioversol
Dosage Form	Injectable
Route	Injection
Strength	74%
Market Status	Prescription
Company	Mallinckrodt

4.2 Drug Indication

Optiray 350 is indicated in adults for peripheral and coronary arteriography and left ventriculography. Optiray 350 is also indicated for contrast enhanced computed tomographic imaging of the head and body, intravenous excretory urography, intravenous digital subtraction angiography and venography. Optiray 350 is indicated in children for angiocardiography. Optiray 320 is indicated in adults for angiography throughout the cardiovascular system. The uses include cerebral, coronary, peripheral, visceral and renal arteriography, venography, aortography, and left ventriculography. Optiray 320 is also indicated for contrast enhanced computed tomographic imaging of the head and body, and intravenous excretory urography. Optiray 320 is indicated in children for angiocardiography, contrast enhanced computed tomographic imaging of the head and body, and intravenous excretory urography. Optiray 300 is indicated for cerebral angiography and peripheral arteriography. Optiray 300 is also indicated for contrast enhanced computed tomographic imaging of the head and body, venography, and intravenous excretory urography. Optiray 240 is indicated for cerebral angiography and venography. Optiray 240 is also indicated for contrast enhanced computed tomographic imaging of the head and body and intravenous excretory urography.

FDA Label

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

IOVERSOL

5.2.2 FDA UNII

N3RIB7X24K

5.2.3 Pharmacological Classes

X-Ray Contrast Activity [MoA]; Radiographic Contrast Agent [EPC]

5.3 ATC Code

V08AB07

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

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

V08AB07 - Ioversol

5.4 Absorption, Distribution and Excretion

Absorption

Ioversol may be visualized in the renal parenchyma within 30 to 60 seconds following rapid intravenous injection. Opacification of the calyces and pelves in patients with normal renal function becomes apparent within 1 to 3 minutes, with optimum contrast occurring within 5 to 15 minutes.

Route of Elimination

Ioversol is excreted mainly through the kidneys following intravascular administration. Greater than 95% of the administered dose was excreted within the first 24 hours, with the peak urine concentration occurring in the first 2 hours after administration. Fecal elimination was negligible.

5.5 Metabolism/Metabolites

No significant metabolism, deiodination or biotransformation occurs.

5.6 Biological Half-Life

1.5 hr

5.7 Mechanism of Action

Intravascular injection of ioversol opacifies those vessels in the path of the flow of the contrast medium, permitting radiographic visualization of the internal structures until significant hemodilution occurs. Optiray enhances computed tomographic imaging through augmentation of radiographic efficiency with the degree of density enhancement directly related to the iodine content in an administered dose.

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