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DSSTox_CID_3163

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Also known as: 73334-07-3, Ultravist, Iopromidum, Iopromida, Proscope, N1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-n1-methylisophthalamide

Molecular Formula

C₁₈H₂₄I₃N₃O₈

Molecular Weight

791.1 g/mol

InChI Key

DGAIEPBNLOQYER-UHFFFAOYSA-N

FDA UNII

712BAC33MZ

Iopromide is a contrast medium.

Iopromide is a Radiographic Contrast Agent. The mechanism of action of iopromide is as a X-Ray Contrast Activity.

1 2D Structure

DSSTox_CID_3163

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-3-N-methylbenzene-1,3-dicarboxamide

2.1.2 InChI

InChI=1S/C18H24I3N3O8/c1-24(4-9(28)6-26)18(31)12-13(19)11(17(30)22-3-8(27)5-25)14(20)16(15(12)21)23-10(29)7-32-2/h8-9,25-28H,3-7H2,1-2H3,(H,22,30)(H,23,29)

2.1.3 InChI Key

DGAIEPBNLOQYER-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(CC(CO)O)C(=O)C1=C(C(=C(C(=C1I)C(=O)NCC(CO)O)I)NC(=O)COC)I

2.2 Other Identifiers

2.2.1 UNII

712BAC33MZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Clarograf

2. Iopromid

3. Lopromid

4. N,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-n-methylisophthalamide

5. Ultravist

6. Ultravist 300

2.3.2 Depositor-Supplied Synonyms

1. 73334-07-3

2. Ultravist

3. Iopromidum

4. Iopromida

5. Proscope

6. N1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-n1-methylisophthalamide

7. Zk 35760

8. 1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-3-n-methylbenzene-1,3-dicarboxamide

9. Zk-35760

10. Magnesium Methanide Propan-1-ide(1:1:1)

11. N,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-n-methylisophthalamide

12. 712bac33mz

13. Ultravist 300

14. Chebi:63578

15. N,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino]-n-methylisophthalamide

16. Ultravist 370

17. Iopromid

18. Dsstox_cid_3163

19. Dsstox_rid_76898

20. Dsstox_gsid_23163

21. 1,3-benzenedicarboxamide, N,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-((methoxyacetyl)amino)-n-methyl-

22. Shl 414c

23. Iopromidum [inn-latin]

24. Iopromida [inn-spanish]

25. Ultravist 150

26. Ultravist 240

27. Einecs 277-385-9

28. Ultravist (pharmacy Bulk)

29. Brn 7085608

30. Unii-712bac33mz

31. Iopromide [usan:usp:inn:ban]

32. Ultravist (tn)

33. Ncgc00016923-01

34. Proscope (tn)

35. Cas-73334-07-3

36. Bay86-4877

37. Bay 86-4877

38. Iopromide [inn]

39. Iopromide [jan]

40. Iopromide [mi]

41. Iopromide [usan]

42. Prestwick0_000872

43. Prestwick1_000872

44. Prestwick2_000872

45. Prestwick3_000872

46. Iopromide [vandf]

47. Iopromide [mart.]

48. Iopromide [usp-rs]

49. Iopromide [who-dd]

50. Chembl1725

51. Iopromide (jan/usp/inn)

52. Schembl24546

53. Bspbio_000943

54. Mls002154045

55. Iopromide, Analytical Standard

56. Spbio_002864

57. Bpbio1_001039

58. Iopromide [ep Impurity]

59. Iopromide [orange Book]

60. Dtxsid0023163

61. Iopromide [ep Monograph]

62. Iopromide [usp Monograph]

63. Hms1570p05

64. Hms2097p05

65. Hms2233o23

66. Hms3370m05

67. Hms3714p05

68. Bcp08449

69. Hy-b1362

70. Tox21_110684

71. Ultravist 300 In Plastic Container

72. Ac-535

73. Mfcd00867924

74. S3207

75. Akos025402129

76. Tox21_110684_1

77. Ccg-220872

78. Db09156

79. Iopromid 100 Microg/ml In Acetonitrile

80. Ncgc00179367-01

81. Ncgc00179367-03

82. 1,3-benzenedicarboxamide, N,n'-bis(2,3-dihydroxypropyl)-5-((methoxyacetyl)amino)-n-methyl-2,4,6-triiodo-

83. Bs-17441

84. Smr001233368

85. Ab00513942

86. Cs-0013103

87. Ft-0627283

88. D01893

89. 334i073

90. Sr-01000841262

91. Q4202805

92. Sr-01000841262-2

93. Iopromide, European Pharmacopoeia (ep) Reference Standard

94. Iopromide, United States Pharmacopeia (usp) Reference Standard

95. Iopromide For System Suitability 1, European Pharmacopoeia (ep) Reference Standard

96. Iopromide For System Suitability 2, European Pharmacopoeia (ep) Reference Standard

97. 1,3-benzenedicarboxamide, N1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-n1-methyl-

98. N,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-n-methyl-5-{[(methyloxy)acetyl]amino}benzene-1,3-dicarboxamide

99. N-(2,3-dihydroxypropyl)-3-[(2,3-dihydroxypropyl)(methyl)carbamoyl]-5-[(1-hydroxy-2-methoxyethylidene)amino]-2,4,6-triiodobenzene-1-carboximidic Acid

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₄I₃N₃O₈
Molecular Weight	791.1 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	6
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	169 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 10
Drug Name	Ultravist
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	62.3%; 49.9%; 76.9%
Market Status	Prescription
Company	Bayer Hlthcare

2 of 10
Drug Name	Ultravist 150
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	31.2%
Market Status	Prescription
Company	Bayer Hlthcare

3 of 10
Drug Name	Ultravist 240
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	49.9%
Market Status	Prescription
Company	Bayer Hlthcare

4 of 10
Drug Name	Ultravist 300
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	62.3%
Market Status	Prescription
Company	Bayer Hlthcare

5 of 10
Drug Name	Ultravist 370
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	76.9%
Market Status	Prescription
Company	Bayer Hlthcare

6 of 10
Drug Name	Ultravist
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	62.3%; 49.9%; 76.9%
Market Status	Prescription
Company	Bayer Hlthcare

7 of 10
Drug Name	Ultravist 150
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	31.2%
Market Status	Prescription
Company	Bayer Hlthcare

8 of 10
Drug Name	Ultravist 240
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	49.9%
Market Status	Prescription
Company	Bayer Hlthcare

9 of 10
Drug Name	Ultravist 300
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	62.3%
Market Status	Prescription
Company	Bayer Hlthcare

10 of 10
Drug Name	Ultravist 370
Active Ingredient	Iopromide
Dosage Form	Injectable
Route	Injection
Strength	76.9%
Market Status	Prescription
Company	Bayer Hlthcare

4.2 Drug Indication

Iopromide, as the product Iovist, is indicated for use as an X-ray contrast agent in the following procedures: Intra-arterial digital subtraction angiography (IA-DSA) (150 mg I/mL) Cerebral arteriography and peripheral arteriography (300 mg I/mL) Coronary arteriography and left ventriculography, visceral angiography and aortography (370 mg I/mL) Peripheral venography (240 mg I/mL) Excretory urography (300 mg I/mL) Contrast computed tomography (CT) imaging of head and body (300 mg I/mL and 370 mg I/mL)

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

IOPROMIDE

5.2.2 FDA UNII

712BAC33MZ

5.2.3 Pharmacological Classes

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

5.3 ATC Code

V08AB05

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

V08AB05 - Iopromide

5.4 Absorption, Distribution and Excretion

Absorption

Following administration, the degree of contrast enhancement is directly related to the iodine content in the administered dose; peak iodine plasma levels occur immediately following rapid intravenous injection. Iodine plasma levels fall rapidly within 5 to 10 minutes, which can be accounted for by the dilution in the vascular and extravascular fluid compartments. Contrast enhancement appears to be greatest immediately after bolus injections (15 seconds to 120 seconds). Thus, greatest enhancement may be detected by a series of consecutive two-to-three second scans performed within 30 to 90 seconds after injection (that is, dynamic computed tomographic imaging). Injection may be visualized in the renal parenchyma within 3060 seconds following rapid intravenous injection. Opacification of the calyces and pelves in patients with normal renal function becomes apparent within 13 minutes, with optimum contrast occurring within 515 minutes.

Route of Elimination

The amounts excreted unchanged in urine represent 97% of the dose in young healthy subjects. Only 2% of the dose is recovered in the feces. Similar recoveries in urine and feces are observed in middle-aged and elderly patients. This finding suggests that, compared to the renal route, biliary and/or gastrointestinal excretion is not important for iopromide. During the slower terminal phase only 3% of the dose is eliminated; 97% of the dose is disposed of during the earlier phases, the largest part of which occurs during the main elimination phase.

Volume of Distribution

16 L

Clearance

The mean total and renal clearances are 107 mL/min and 104 mL/min, respectively.

5.5 Metabolism/Metabolites

Iopromide is not metabolized.

5.6 Biological Half-Life

After intravenous administration to healthy young volunteers, plasma iopromide concentration time profile shows an initial distribution phase with a half-life of 0.24 hour; a main elimination phase with a half-life of 2 hours; and a terminal elimination phase with a half-life of 6.2 hours.

5.7 Mechanism of Action

Iopromide is a low osmolar, non-ionic X-ray contrast agent for intravascular administration. It functions as a contrast agent by opacifying blood vessels in the path of flow of the contrast agent, permitting radiographic visualization of the internal structures until significant hemodilution occurs.