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Chemistry

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Also known as: 92339-11-2, Visipaque, Indixanol, Iodixanolum, 2-5410-3a, Hw8w27htxx
Molecular Formula
C35H44I6N6O15
Molecular Weight
1550.2  g/mol
InChI Key
NBQNWMBBSKPBAY-UHFFFAOYSA-N
FDA UNII
HW8W27HTXX

Iodixanol
Iodixanol is a dimeric iso-osmolar, non-ionic, hydrophilic iodinated radiocontrast agent used in diagnostic imaging. Upon intravascular administration and during computed tomography (CT) imaging, iodixanol blocks x-rays and appears opaque on x-ray images. This allows body structures that absorb iodine to be visualized. The degree of opacity produced by iodixanol is directly proportional to the total amount of the iodinated contrast agent in the path of the x-rays. The visualization of body structures is dependent upon the distribution and elimination of iodixanol. Compared to other iodinated contrast agents, iodixanol appears to exhibit less nephrotoxicity.
Iodixanol is a Radiographic Contrast Agent. The mechanism of action of iodixanol is as a X-Ray Contrast Activity.
1 2D Structure

Iodixanol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[acetyl-[3-[N-acetyl-3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
2.1.2 InChI
InChI=1S/C35H44I6N6O15/c1-13(52)46(30-26(38)20(32(59)42-3-15(54)9-48)24(36)21(27(30)39)33(60)43-4-16(55)10-49)7-19(58)8-47(14(2)53)31-28(40)22(34(61)44-5-17(56)11-50)25(37)23(29(31)41)35(62)45-6-18(57)12-51/h15-19,48-51,54-58H,3-12H2,1-2H3,(H,42,59)(H,43,60)(H,44,61)(H,45,62)
2.1.3 InChI Key
NBQNWMBBSKPBAY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)N(CC(CN(C1=C(C(=C(C(=C1I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I)C(=O)C)O)C2=C(C(=C(C(=C2I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I
2.2 Other Identifiers
2.2.1 UNII
HW8W27HTXX
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Contrast Media 2-5410-3

2. Iodixanol-320

3. Visipaque

4. Visipaque Unique Softpac

2.3.2 Depositor-Supplied Synonyms

1. 92339-11-2

2. Visipaque

3. Indixanol

4. Iodixanolum

5. 2-5410-3a

6. Hw8w27htxx

7. Nsc-760069

8. 5,5'-((2-hydroxytrimethylene)bis(acetylimino))bis(n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

9. Chebi:31705

10. 5-[acetyl-[3-[n-acetyl-3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

11. 2-541o-3a

12. Dsstox_cid_25523

13. Dsstox_rid_80929

14. Dsstox_gsid_45523

15. 1,3-benzenedicarboxamide, 5,5'-((2-hydroxy-1,3-propanediyl)bis(acetylimino))bis(n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

16. 5-[acetyl-[3-[n-acetyl-3,5-bis[[(2s)-2,3-dihydroxypropyl]carbamoyl]-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-1-n,3-n-bis[(2s)-2,3-dihydroxypropyl]-2,4,6-triiodobenzene-1,3-dicarboxamide

17. Optiprep; Visipaque; Visipaque 270;2-5410-3a

18. Visipaque 270

19. Visipaque 320

20. Iodixanolum [latin]

21. Optiprep

22. 1,3-benzenedicarboxamide, 5,5'-[(2-hydroxy-1,3-propanediyl)bis(acetylimino)]bis[n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

23. 5,5'-((2-hydroxypropane-1,3-diyl)bis(acetylazanediyl))bis(n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

24. Ccris 7567

25. Sr-01000872678

26. Unii-hw8w27htxx

27. Hsdb 8076

28. Iodixanol [usan:usp:inn:ban]

29. Visipaque (tn)

30. Ncgc00016958-01

31. Cas-92339-11-2

32. Visipaque;iodixanolum

33. Iodixanol [inn]

34. Iodixanol [jan]

35. Iodixanol [mi]

36. Iodixanol [usan]

37. Prestwick0_000848

38. Prestwick1_000848

39. Prestwick2_000848

40. Prestwick3_000848

41. Iodixanol [vandf]

42. Iodixanol [mart.]

43. Ec 618-837-0

44. Iodixanol [usp-rs]

45. Iodixanol [who-dd]

46. Iodixanol (jan/usp/inn)

47. Schembl21546

48. Bspbio_000835

49. Spbio_002756

50. Bpbio1_000919

51. Iodixanol [orange Book]

52. Chembl1200507

53. Dtxsid2045523

54. Iodixanol [ep Monograph]

55. Iodixanol [usp Impurity]

56. Iodixanol [usp Monograph]

57. Hms1570j17

58. Hms2097j17

59. Hms3714j17

60. Pharmakon1600-01503835

61. Bcp11111

62. Hy-b1426

63. Tox21_110711

64. Nsc760069

65. S5218

66. Akos015895607

67. Tox21_110711_1

68. Ac-7610

69. Ccg-213207

70. Db01249

71. Nsc 760069

72. Ncgc00179408-01

73. Ncgc00179408-03

74. 5-(acetyl-(3-(acetyl-(3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodophenyl)amino)-2- Hydroxypropyl)amino)-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide; 5,5'-((2-hydroxytrimethylene)bis(acetylimino))bis(n,n'-bis(2,3-dihydroxypropyl)-2,4,6- Triiodoisophthalamide);

75. Ab00513936

76. Cs-0013137

77. Ft-0627254

78. Ft-0645028

79. D01474

80. Ab00513936_02

81. 339i112

82. A844203

83. Q2419291

84. Sr-01000872678-1

85. Sr-01000872678-2

86. Brd-a08660406-001-01-8

87. Optiprep(tm) Density Gradient Medium, Used For Cell And Subcellular Organelle Isolation

88. 5,5'-(2-hydroxypropane-1,3-diyl)bis(acetylazanediyl)bis(n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

89. 5,5'-[(2-hydroxypropane-1,3-diyl)bis(acetylimino)]bis[n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide]

90. 5,5-[(2-hydroxy-1,3-propanediyl)bis(acetylimino)]bis[n,n-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

91. 5-[[3-[[3,5-bis[2,3-bis(oxidanyl)propylcarbamoyl]-2,4,6-tris(iodanyl)phenyl]-ethanoyl-amino]-2-oxidanyl-propyl]-ethanoyl-amino]-n1,n3-bis[2,3-bis(oxidanyl)propyl]-2,4,6-tris(iodanyl)benzene-1,3-dicarboxamide

92. 5-[acetyl-[3-[n-acetyl-3,5-bis[(2,3-dihydroxypropylamino)-oxomethyl]-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

93. 5-{n-[3-(n-{3,5-bis[(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodophenyl}acetamido)-2-hydroxypropyl]acetamido}-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 1550.2 g/mol
Molecular Formula C35H44I6N6O15
XLogP3-3.4
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count15
Rotatable Bond Count22
Exact Mass1549.7133 g/mol
Monoisotopic Mass1549.7133 g/mol
Topological Polar Surface Area339 Ų
Heavy Atom Count62
Formal Charge0
Complexity1330
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count4
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 NameVisipaque 270
Active IngredientIodixanol
Dosage FormInjectable
RouteInjection
Strength55%
Market StatusPrescription
CompanyGe Healthcare

2 of 4  
Drug NameVisipaque 320
Active IngredientIodixanol
Dosage FormInjectable
RouteInjection
Strength65.2%
Market StatusPrescription
CompanyGe Healthcare

3 of 4  
Drug NameVisipaque 270
Active IngredientIodixanol
Dosage FormInjectable
RouteInjection
Strength55%
Market StatusPrescription
CompanyGe Healthcare

4 of 4  
Drug NameVisipaque 320
Active IngredientIodixanol
Dosage FormInjectable
RouteInjection
Strength65.2%
Market StatusPrescription
CompanyGe Healthcare

4.2 Therapeutic Uses

Iodixanol is indicated for contrast enhanced computerized tomography imaging of the head and body, excretory urography, and peripheral venography. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


Iodixanol is indicated for angiocardiography (left ventriculography and selective coronary arteriography), peripheral arteriography, visceral arteriography, and cerebral arteriography. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


Iodixanol is indicated for intra-arterial digital subtraction angiography. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


Iodixanol is indicated for contrast enhanced computerized tomography imaging of the head and body, and excretory urography. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


For more Therapeutic Uses (Complete) data for Iodixanol (6 total), please visit the HSDB record page.


4.3 Drug Warning

The following selected adverse events were reported in ?0.5% of the 1244 patients in controlled clinical trials who received iodixanol injection: General Disorders: back pain, fatigue, malaise; Cardiovascular Disorders: arrhythmias, cardiac failure, conduction abnormalities, hypotension, myocardial infarction; Nervous System: cerebral vascular disorder, convulsions, hypoesthesia, stupor, confusion; Gastrointestinal System Disorders: dyspepsia; Hypersensitivity Disorders: pharyngeal edema; Respiratory System Disorders: asthma, bronchitis, dyspnea, pulmonary edema, rhinitis; Renal System Disorders: abnormal renal function, acute renal failure, hematuria; Peripheral Vascular Disorders: flushing, peripheral ischemia; Skin and Appendage Disorders: hematoma, increased sweating; Special Senses, Other Disorders: tinnitus; Vision Disorders: abnormal vision.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


Additional adverse events reported in other clinical studies and in foreign postmarketing surveillance and foreign clinical trials with the use of iodixanol injection are: anaphylactic reactions, anaphylactoid reactions, hypoglycemia, amnesia, cardiac arrest, hypertension, dyskinesia, hemorrhage not otherwise specified, polymyalgia rheumatica, pulmonary embolism, respiratory depression, and cortical blindness.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


... Selected commonly reported adverse events in pediatrics include: vomiting, nausea, fever, rash, and pruritus. Less frequently reported events are apnea, disseminated intravascular coagulation, atrioventricular block and bundle branch block, arrhythmia, cardiac failure, renal failure and taste perversion.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


In patients with normal blood-brain barriers and renal failure, iodinated contrast agents have been associated with blood-brain barrier disruption and accumulation of contrast in the brain.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


For more Drug Warnings (Complete) data for Iodixanol (28 total), please visit the HSDB record page.


4.4 Drug Indication

Iodixanol is a contrast agent during coronary angiography.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Iodixanol is a contrast agent commonly used during coronary angiography, particularly in individuals with renal dysfunction, as it is believed to be less toxic to the kidneys than most other intravascular contrast agents. It is an imaging contrast agent with the same osmolality as blood (290mOsm/kg H20).


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
IODIXANOL
5.3.2 FDA UNII
HW8W27HTXX
5.3.3 Pharmacological Classes
X-Ray Contrast Activity [MoA]; Radiographic Contrast Agent [EPC]
5.4 ATC Code

V08AB09

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

V08AB09 - Iodixanol


5.5 Absorption, Distribution and Excretion

Route of Elimination

In adults, approximately 97% of the injected dose of iodixanol is excreted unchanged in urine within 24 hours, with less than 2% excreted in feces within five days post-injection.


Volume of Distribution

0.26 L/kg


Absorption and excretion of iodixanol 320 mg I/ml were investigated in rats after intragastric administration of 2.5 g I/kg b.w. Animals were observed for up to 96 hours after treatment, and blood, urine and feces taken at several time-points throughout the experiment. Concentrations of iodixanol in serum and urine were measured by means of reversed-phase high-performance liquid chromatography. Fecal concentrations of iodixanol, based on iodine measurements, were determined by X-ray fluorescence spectrometry. Serial radiographs were obtained and histopathological examination was performed on selected tissues. The results indicate that less than 1% of the intragastric dose of iodixanol is absorbed from the intestine into the blood stream. No adverse clinical signs were observed, and there were no treatment-related histomorphological findings.

PMID:8610524 Dunkel JA et al; Acta Radiol Suppl 399: 253-7 (1995)


In 40 healthy, young male volunteers receiving a single intravenous administration of iodixanol injection in doses of 0.3 to 1.2 gI/kg body weight, ... renal clearance was 110 mL/min (+/-14), equivalent to glomerular filtration (108 mL/min). These values were independent of the dose administered.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


... In a study of 16 adult patients who were scheduled for renal transplant, the elimination of iodixanol 320 mgI/mL was studied. The patients' baseline mean creatinine levels were 6.3 mg/dL (+/-1.5) and mean creatinine clearances were 13.61 mL/min (+/- 4.67). ... In these patients, levels of iodixanol were detected 5 days after dosing. Contrast enhancement time in kidneys increased from 6 hours to at least 24 hours. ...

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


Plasma and urine levels suggest that body clearance of iodixanol is primarily due to renal clearance. In adults, approximately 97% of the injected dose of iodixanol is excreted unchanged in urine within 24 hours, with less than 2% excreted in feces within five days post-injection.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


For more Absorption, Distribution and Excretion (Complete) data for Iodixanol (14 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Excreted unchanged


Iodixanol metabolites have not been demonstrated.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


5.7 Biological Half-Life

2.1 hours. In patients with significantly impaired renal function (mean creatinine clearance rate, 9.91 [± 3.58] mL per minute), the plasma half-life is increased to 23 hours.


Forty pediatric patients < or = 12 years old, with renal function that is normal for their age, received multiple intra-arterial administrations of iodixanol injection in doses of 0.32 to 3.2 gI/kg body weight. The elimination half-lives for these patients are ...: 0.185 hr -1 (newborn to 2 months old), 0.256 hr -1 (2 to <6 months old), 0.299 hr -1 (6 months to<1 year), 0.322 hr -1 (1 to<2 years), and 0.307 hr -1 (2 to < or = 12 years old). The adult mean terminal elimination rate constant is 0.336 hr-1. ...

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


In 40 healthy, young male volunteers receiving a single intravenous administration of iodixanol injection in doses of 0.3 to 1.2 gI/kg body weight, the elimination half-life was 2.1 hr (+/- 0.1) ...

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


... Iodixanol was rapidly excreted, mainly via the kidneys, with a plasma half-life in rats and monkeys of 25 and 76 mins, respectively. ...

PMID:8610532 Heglund IF et al; Acta Radiol Suppl 399: 69-82 (1995)


... In a study of 16 adult patients who were scheduled for renal transplant, the elimination of iodixanol 320 mgI/mL was studied. ... In these patients, the plasma half-life was increased to 23 hours (normal t1/2 = 2 hours). ...

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


5.8 Mechanism of Action

Organic iodine compounds attenuate x-rays as they pass through the body, thereby allowing the body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. After intravascular administration, iodixanol makes opaque those internal structures in its path of flow, allowing their visualization until significant hemodilution and elimination occur.


Intravascular injection of iodixanol opacifies those vessels in the path of flow of the contrast agent, permitting radiographic visualization of the internal structures until significant dilution and elimination occurs.

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e


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