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Chemistry

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Also known as: Adipiodone, 606-17-7, Iodipamic acid, Cholografin, Bilignost, Bilignostum
Molecular Formula
C20H14I6N2O6
Molecular Weight
1139.8  g/mol
InChI Key
FFINMCNLQNTKLU-UHFFFAOYSA-N
FDA UNII
TKQ858A3VW

Iodipamide
A water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.
Iodipamide is a Radiographic Contrast Agent. The mechanism of action of iodipamide is as a X-Ray Contrast Activity.
1 2D Structure

Iodipamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[[6-(3-carboxy-2,4,6-triiodoanilino)-6-oxohexanoyl]amino]-2,4,6-triiodobenzoic acid
2.1.2 InChI
InChI=1S/C20H14I6N2O6/c21-7-5-9(23)17(15(25)13(7)19(31)32)27-11(29)3-1-2-4-12(30)28-18-10(24)6-8(22)14(16(18)26)20(33)34/h5-6H,1-4H2,(H,27,29)(H,28,30)(H,31,32)(H,33,34)
2.1.3 InChI Key
FFINMCNLQNTKLU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(C(=C(C(=C1I)NC(=O)CCCCC(=O)NC2=C(C=C(C(=C2I)C(=O)O)I)I)I)C(=O)O)I
2.2 Other Identifiers
2.2.1 UNII
TKQ858A3VW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Adipiodon

2. Bilignost

3. Biligrafine

4. Bilipolinum

5. Cholografin

6. Endocistobil

7. Endographin

2.3.2 Depositor-Supplied Synonyms

1. Adipiodone

2. 606-17-7

3. Iodipamic Acid

4. Cholografin

5. Bilignost

6. Bilignostum

7. Cholospect

8. Biligrafin

9. Transbilix

10. Adipiodona

11. Adipiodonum

12. Adipiodonum [inn-latin]

13. Adipiodona [inn-spanish]

14. 3,3'-[(1,6-dioxohexane-1,6-diyl)diimino]bis(2,4,6-triiodobenzoic Acid)

15. 3,3'-(adipoyldiimino)bis(2,4,6-triiodobenzoic Acid)

16. Adipiodone [inn]

17. 3-[[6-(3-carboxy-2,4,6-triiodoanilino)-6-oxohexanoyl]amino]-2,4,6-triiodobenzoic Acid

18. Adipiodon

19. Tkq858a3vw

20. Iodipamide Meglumine

21. Benzoic Acid, 3,3'-((1,6-dioxo-1,6-hexanediyl)diimino)bis(2,4,6-triiodo-

22. Nsc-757423

23. 3-[5-[(3-carboxy-2,4,6-triiodo-phenyl)carbamoyl]pentanoylamino]-2,4,6-triiodo-benzoic Acid

24. Ncgc00016523-03

25. Cas-606-17-7

26. Dsstox_cid_3153

27. Benzoic Acid, 3,3'-[(1,6-dioxo-1,6-hexanediyl)diimino]bis[2,4,6-triiodo-

28. Dsstox_rid_76893

29. Adipic Acid Di(3-carboxy-2,4,6-triiodoanilide)

30. Dsstox_gsid_23153

31. 3,3-adipoyldiiminobis(2,4,6-triiodobenzoic Acid)

32. Iodipamide (usp)

33. Adipiodone (jan/inn)

34. Iodipamide [usp:inn]

35. Einecs 210-105-5

36. Unii-tkq858a3vw

37. Biligrafine

38. Brn 2230896

39. N,n''-adipoyl-bis(3-amino-2,4,6-triiodbenzoesaeure)

40. Hsdb 8066

41. Starbld0009605

42. Iodipamide (adipiodone)

43. Iodipamide [mi]

44. Adipiodone [jan]

45. Prestwick0_000939

46. Prestwick1_000939

47. Prestwick2_000939

48. Prestwick3_000939

49. Adipiodone [mart.]

50. Adipiodone [who-dd]

51. Iodipamide [usp-rs]

52. Schembl37678

53. Bspbio_000878

54. 4-14-00-01122 (beilstein Handbook Reference)

55. Mls001066414

56. 3,3'-adipoyldiiminobis(2,4,6-triiodobenzoic Acid)

57. Spbio_003047

58. 3,3'(adipoyldiimino)bis(2,4,6-triiodobenzoic Acid)

59. Bpbio1_000966

60. Gtpl7400

61. Benzoic Acid, 3,3'-(adipoyldiimino)bis(2,4,6-triiodo-

62. Chembl1165268

63. Dtxsid6023153

64. Chebi:31176

65. Hms1570l20

66. Hms2097l20

67. Hms2232c09

68. Hms3370i13

69. Hms3714l20

70. Iodipamide [usp Monograph]

71. Hy-b1292

72. Tox21_113504

73. Mfcd00058983

74. Akos015964892

75. Tox21_113504_1

76. Ccg-220939

77. Db04711

78. Nsc 757423

79. Ncgc00016523-01

80. Ncgc00016523-02

81. Ncgc00016523-04

82. Ncgc00016523-05

83. Smr000471884

84. Db-053672

85. Ab00513970

86. Cs-0013062

87. Ft-0627253

88. I0299

89. D01774

90. Iodipamide, Analytical Standard, For Drug Analysis

91. Sr-01000760542

92. Q4682934

93. Sr-01000760542-2

94. Brd-k67261995-001-03-4

95. Iodipamide, United States Pharmacopeia (usp) Reference Standard

96. 3-{5-[(3-carboxy-2,4,6-triiodophenyl)carbamoyl]pentanamido}-2,4,6-triiodobenzoic Acid

97. 3-[[6-[(3-carboxy-2,4,6-triiodophenyl)amino]-6-oxohexanoyl]amino]-2,4,6-triiodobenzoic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 1139.8 g/mol
Molecular Formula C20H14I6N2O6
XLogP35.5
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass1139.5120 g/mol
Monoisotopic Mass1139.5120 g/mol
Topological Polar Surface Area133 Ų
Heavy Atom Count34
Formal Charge0
Complexity714
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Contrast Media

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Cholografin Meglumine is indicated for intravenous cholangiography and cholecystography as follows: (a) visualization of the gallbladder and biliary ducts in the differential diagnosis of acute abdominal conditions, (b) visualization of the biliary ducts, especially in patients with symptoms after cholecystectomy, and (c) visualization of the gallbladder in patients unable to take oral contrast media or to absorb contrast media from the gastrointestinal tract. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for cholografin meglumine (Iodipamide Meglumine) injection, solution (June 2008). Available from, as of July 9, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=430c343b-bad6-4584-8c63-05bca0b203a2


THERAPEUTIC CATEGORY: Diagnostic aid (radiopaque medium-cholecystographic)

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 873


THERAPEUTIC CATEGORY (VETERINARY): Diagnostic aid (radiopaque medium)

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 873


4.2 Drug Warning

Iodipamide meglumine is contraindicated for use in intrathecal procedures.

US Natl Inst Health; DailyMed. Current Medication Information for cholografin meglumine (Iodipamide Meglumine) injection, solution (June 2008). Available from, as of July 9, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=430c343b-bad6-4584-8c63-05bca0b203a2


Iodipamide meglumine is contraindicated in patients with a hypersensitivity to salts of iodipamide or who exhibit sensitivity reactions to the test dose. It is also contraindicated in patients with concomitant severe impairment of renal and liver function.

US Natl Inst Health; DailyMed. Current Medication Information for cholografin meglumine (Iodipamide Meglumine) injection, solution (June 2008). Available from, as of July 9, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=430c343b-bad6-4584-8c63-05bca0b203a2


Serious adverse reactions have been reported due to the inadvertent intrathecal administration of iodinated contrast media that are not indicated for intrathecal use. These serious adverse reactions include: death, convulsions, cerebral hemorrhage, coma, paralysis, arachnoiditis, acute renal failure, cardiac arrest, seizures, rhabdomyolysis, hyperthermia, and brain edema. Special attention must be given to insure that this drug product is not inadvertently administered intrathecally.

US Natl Inst Health; DailyMed. Current Medication Information for cholografin meglumine (Iodipamide Meglumine) injection, solution (June 2008). Available from, as of July 9, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=430c343b-bad6-4584-8c63-05bca0b203a2


The possibility exists for inadvertent administration into the intrathecal space during epidural administrations. Therefore, epidural administration procedures, such as pain management catheter placement, should not be performed with use of this product.

US Natl Inst Health; DailyMed. Current Medication Information for cholografin meglumine (Iodipamide Meglumine) injection, solution (June 2008). Available from, as of July 9, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=430c343b-bad6-4584-8c63-05bca0b203a2


For more Drug Warnings (Complete) data for Iodipamide (15 total), please visit the HSDB record page.


4.3 Drug Indication

Iodipamide is used as a contrast agent for cholecystography and intravenous cholangiography.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Following intravenous administration of Cholografin Meglumine, iodipamide is carried to the liver where it is rapidly secreted. The contrast medium appears in the bile within 10 to 15 minutes after injection, thus permitting visualization of the hepatic and common bile ducts, even in cholecystectomized patients. The biliary ducts are readily visualized within about 25 minutes after administration, except in patients with impaired liver function. The gallbladder begins to fill within an hour after injection; maximum filling is reached after two to two and one-half hours. The contrast medium is finally eliminated in the feces without passing through the enterohepatic circulation, except for approximately 10 percent of the intravenously administered dose which is excreted through the kidneys.


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
IODIPAMIDE
5.3.2 FDA UNII
TKQ858A3VW
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

V08AC - Watersoluble, hepatotropic x-ray contrast media

V08AC04 - Adipiodone


5.5 Absorption, Distribution and Excretion

To characterize the saturation kinetics of iodipamide, timed samples of blood, urine, and bile were taken from two unanesthetized dogs infused with iodipamide at increasing rates to achieve various steady state blood concentrations. Biliary excretion rate of iodipamide reached an asymptote with increasing blood concentration, indicating a biliary transport maximum (Tm) of 15.2 to 16.2 mgI/min. Urinary excretion was not a pure, first order process and urinary excretion rate was higher than the glomerular filtration rate corrected for plasma protein binding, suggesting that active tubular secretion may play a part. Extrarenal elimination followed Michaelis-Menten kinetics. Estimates of maximum rate (Vm) and Michaelis-Menten constant (Km) were obtained graphically. The estimated values of Vm were 4 to 6 times that of biliary Tm. In acute infusion experiments the iodipamide excreted in the bile and urine and that remaining in the organs analyzed accounted for only a fraction of the dose administered; no significant accumulation of iodipamide was found in the liver.

PMID:856758 Lin SK et al; Invest Radiol 12 (2): 175-9 (1977)


The contrast agent for biliary tract visualization, iodipamide, is strongly bound to serum albumin. The relationship between the affinity of the contrast agent for albumin and its preferential uptake and excretion by the liver has been unclear. The role of serum albumin on hepatic uptake and excretion of iodipamide therefore was investigated on the isolated perfused rabbit liver. With the perfusate containing fully reconstituted rabbit plasma protein or 3.5 g/100 mL rabbit albumin alone, the iodipamide excretion is initially extremely slow. It then increases gradually to about 6 mug/gm liver per min by 60 minutes and thereafter remains constant. The half-time of transfer to the bile is about 130 min. Without albumin in the perfusate the initial clearance rate of iodipamide is rapid, with half-time transfer to the bile of about 40 min. Rabbit serum globulins have no effect on iodipamide excretion. Thus, binding of iodipamide to albumin retards the transfer of iodipamide from plasma to the bile, probably due to competition between albumin and the anion binding protein of the liver.

PMID:1254421 Song CS et al; Invest Radiol 11 (1): 39-44 (1976)


The contrast medium is eliminated in the feces without passing through the enterohepatic circulation, except for approximately 10 percent of the intravenously administered dose which is excreted through the kidneys.

US Natl Inst Health; DailyMed. Current Medication Information for cholografin meglumine (Iodipamide Meglumine) injection, solution (June 2008). Available from, as of July 9, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=430c343b-bad6-4584-8c63-05bca0b203a2


5.6 Metabolism/Metabolites

Hepatic.


5.7 Mechanism of Action

Organic iodine compounds block x-rays as they pass through the body, thereby allowing body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these iodinated organic compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. Iodipamide's primary excretion through the hepato-biliary system and concentration in bile allows visualization of the gallbladder and biliary ducts.


... The iodine in the contrast medium is responsible for the absorption of x-rays and the resulting opacification of the organ system or other area under investigation. ...

PMID:3902331 Swanson DP et al; Clin Pharm 4 (5): 527-38 (1985)


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