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Gadodiamide
Also known as: Gadodiamide, 131410-48-5, Omniscan, 2-[bis[2-[carboxylatomethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetate;gadolinium(3+), 122795-43-1, Omniscan (tn)
Molecular Formula
C16H26GdN5O8
Molecular Weight
573.7  g/mol
InChI Key
HZHFFEYYPYZMNU-UHFFFAOYSA-K
FDA UNII
84F6U3J2R6

Gadodiamide is a paramagnetic gadolinium-based contrast agent (GBCA), with imaging activity upon magnetic resonance imaging (MRI). When placed in a magnetic field, gadodiamide generates a large local magnetic field, which can enhance the relaxation rate of nearby protons. This change in proton relaxation dynamics, iincreases the MRI signal intensity of tissues in which gadodiamide has accumulated; therefore, visualization of those tissues is enhanced.
Gadodiamide is a Paramagnetic Contrast Agent. The mechanism of action of gadodiamide is as a Magnetic Resonance Contrast Activity.
1 2D Structure

Gadodiamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[bis[2-[carboxylatomethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetate;gadolinium(3+)
2.1.2 InChI
InChI=1S/C16H29N5O8.Gd/c1-17-12(22)7-20(10-15(26)27)5-3-19(9-14(24)25)4-6-21(11-16(28)29)8-13(23)18-2;/h3-11H2,1-2H3,(H,17,22)(H,18,23)(H,24,25)(H,26,27)(H,28,29);/q;+3/p-3
2.1.3 InChI Key
HZHFFEYYPYZMNU-UHFFFAOYSA-K
2.1.4 Canonical SMILES
CNC(=O)CN(CCN(CCN(CC(=O)NC)CC(=O)[O-])CC(=O)[O-])CC(=O)[O-].[Gd+3]
2.2 Other Identifiers
2.2.1 UNII
84F6U3J2R6
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gadodiamide

2. Gd-dtpa Bis-(methylamide)

3. Gd-dtpa-bma

4. Omniscan

5. Omniscan Unique Softpack

2.3.2 Depositor-Supplied Synonyms

1. Gadodiamide

2. 131410-48-5

3. Omniscan

4. 2-[bis[2-[carboxylatomethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetate;gadolinium(3+)

5. 122795-43-1

6. Omniscan (tn)

7. Gadodiamide Anhydrous

8. Gadodiamide, Gd-dtpa-bma

9. 84f6u3j2r6

10. Gddtpa-bma

11. Gadodiamide (usp/inn)

12. Gadodiamide [mi]

13. Gadodiamide [inn]

14. S-041

15. Gadodiamide [hsdb]

16. Gadodiamide [usan]

17. Gadodiamide [vandf]

18. Gadodiamide [mart.]

19. Schembl73031

20. Gadodiamide [usp-rs]

21. Gadodiamide [who-dd]

22. Gadodiamide [orange Book]

23. Dtxsid201019701

24. Moli001033

25. Gadodiamide [usp Monograph]

26. Ac-925

27. Mfcd00867269

28. Akos015900642

29. Db-042031

30. D04284

31. 4-(n-(1,8-naphthalimido))-n-butyricacid

32. A806259

33. F02-0056

34. J-004857

35. (5,8-bis(carboxymethyl)-11-(2-(methylamino)-2-oxoethyl)-3-oxo-2,5,8,11-tetraazatridecan-13-oato(3-))gadolinium

36. (n,n-bis(2-((carboxymethyl)((methylcarbamoyl)methyl)amino)ethyl)glycinato(3-))gadolinium

37. 2-[bis[2-[[2-(methylamino)-2-oxidanylidene-ethyl]-(2-oxidanidyl-2-oxidanylidene-ethyl)amino]ethyl]amino]ethanoate; Gadolinium(3+)

38. 2-[bis[2-[carboxylatomethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetate; Gadolinium(3+)

39. Gadolinium(iii) 5,8-bis(carboxylatomethyl)-2-[2-(methylamino)-2-oxoethyl]-10-oxo-2,5,8,11-tetraazadodecane-1-carboxylate

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 573.7 g/mol
Molecular Formula C16H26GdN5O8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count13
Exact Mass574.10225 g/mol
Monoisotopic Mass574.10225 g/mol
Topological Polar Surface Area188 Ų
Heavy Atom Count30
Formal Charge0
Complexity527
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Contrast Media

National Library of Medicine's Medical Subject Headings. Gadodiamide. Online file (MeSH, 2014). Available from, as of October 23, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html


Omniscan is a gadolinium-based contrast agent indicated for intravenous use in MRI to visualize lesions with abnormal vascularity (or those thought to cause abnormalities in the blood-brain barrier) in the brain (intracranial lesions), spine, and associated tissues. /Included in US product label/

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


Omniscan is a gadolinium-based contrast agent indicated for intravenous use in MRI to facilitate the visualization of lesions with abnormal vascularity within the thoracic (noncardiac), abdominal, pelvic cavities, and the retroperitoneal space. /Included in US product label/

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


... To evaluate the safety and effectiveness of gadodiamide-enhanced magnetic resonance (MR) angiography with single and triple doses in the assessment of abdominal arterial stenoses ... One hundred five patients were included in the randomized, double-blind, phase III multicenter trial. Results of MR angiography with 0.1 mmol/kg and 0.3 mmol/kg doses of gadodiamide were compared with those of digital subtraction angiography (DSA) and according to dose ... No serious adverse events were observed. The mean contrast index at the region proximal to the primary stenosis was significantly higher in the triple-dose group (P = 0.03). Mean 95% CI values for the difference in depicted degree of stenosis between DSA and postcontrast MR angiography improved from -3.4% +/- 4.7 (SD) in the single-dose group to -1.2% +/- 4.7 in the triple-dose group. Mean values for overall image quality on the visual analogue scale improved with the triple dose (P = 0.02). Confidence in diagnosis was high at postcontrast MR angiography in 88% and 96% of cases in the single- and triple-dose groups, respectively ... Gadodiamide-enhanced MR angiography performed with single and triple doses is safe and effective for assessing major abdominal arterial stenoses. Although high agreement between MR angiography and DSA was achieved with both doses, triple-dose MR angiography was superior in the evaluations of image quality, degree of arterial stenoses, and confidence in diagnosis.

PMID:11274548 Thurnher SA et al; Radiology 219 (1): 137-46 (2001)


... The safety and diagnostic efficacy of MultiHance (gadobenate dimeglumine) in the central nervous system (CNS) were evaluated in a double-blind, multicenter, phase III clinical trial ... Two hundred five patients highly suspected of having a CNS lesion (by previous imaging exam) were enrolled at 16 sites in the United States. Patients were randomized to one of three incremental dosing regimens. Magnetic resonance imaging with Omniscan (gadodiamide) at doses of 0.1 and 0.3 mmol/kg was compared with MultiHance (gadobenate dimeglumine) at doses of 0.05 and 0.15 mmol/kg and at 0.1 and 0.2 mmol/kg ... Compared with predose images alone, efficacy was demonstrated in each of the gadobenate dimeglumine and gadodiamide groups (single and cumulative doses) as indicated by the level of diagnostic information, number of lesions detected, and contrast-to-noise ratio measurements. The level of diagnostic information from gadobenate dimeglumine at 0.1 mmol/kg was equivalent to that with gadodiamide at the same dose. One of the two blinded reviewers found equivalence between the gadobenate dimeglumine 0.05 mmol/kg dose and gadodiamide at 0.1 mmol/kg. Both reviewers found the level of diagnostic information to be equivalent after the second dose of contrast for all three dosing regimens. The cumulative doses of gadobenate dimeglumine were well tolerated and as safe as gadodiamide ... Gadobenate dimeglumine is comparable to gadodiamide in terms of safety and efficacy for imaging of CNS lesions, with a possible advantage in imaging applications owing to enhanced T1 relaxivity.

PMID:11224753 Runge VM et al; Invest Radiol 36(2):65-71 (2001)


4.2 Drug Warning

/BOXED WARNING/ WARNING: NOT FOR INTRATHECAL USE AND NEPHROGENIC SYSTEMIC FIBROSIS (NSF). NOT FOR INTRATHECAL USE: Inadvertent intrathecal use of OMNISCAN has caused convulsions, coma, sensory and motor neurologic deficits. NEPHROGENIC SYSTEMIC FIBROSIS (NSF): Gadolinium-based contrast agents (GBCAs) increase the risk for NSF among patients with impaired elimination of the drugs. Avoid use of GBCAs in these patients unless the diagnostic information is essential and not available with non-contrasted MRI or other modalities. NSF may result in fatal or debilitating fibrosis affecting the skin, muscle and internal organs. Do not administer Omniscan to patients with: chronic, severe kidney disease (GFR < 30 mL/min/1.73 sq m), or acute kidney injury. Screen patients for acute kidney injury and other conditions that may reduce renal function. For patients at risk for chronically reduced renal function (e.g., age > 60 years, hypertension or diabetes), estimate the glomerular filtration rate (GFR) through laboratory testing. Do not exceed the recommended Omniscan dose and allow a sufficient period of time for elimination of the drug from the body prior to any readministration

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


Gadolinium-based contrast agents (GBCAs) increase the risk for nephrogenic systemic fibrosis (NSF) among patients with impaired elimination of the drugs. Avoid use of GBCAs among these patients unless the diagnostic information is essential and not available with non-contrast enhanced MRI or other modalities. The GBCA-associated NSF risk appears highest for patients with chronic, severe kidney disease (GFR < 30 mL/min/1.73 sq m) as well as patients with acute kidney injury. Do not administer Omniscan to these patients. The risk appears lower for patients with chronic, moderate kidney disease (GFR 30-59 mL/min/1.73 sq m) and little, if any, for patients with chronic, mild kidney disease (GFR 60-89 mL/min/1.73 sq m). NSF may result in fatal or debilitating fibrosis affecting the skin, muscle and internal organs. ... Screen patients for acute kidney injury and other conditions that may reduce renal function. Features of acute kidney injury consist of rapid (over hours to days) and usually reversible decrease in kidney function, commonly in the setting of surgery, severe infection, injury or drug-induced kidney toxicity. Serum creatinine levels and estimated GFR may not reliably assess renal function in the setting of acute kidney injury. For patients at risk for chronically reduced renal function (e.g., age > 60 years, diabetes mellitus or chronic hypertension), estimate the GFR through laboratory testing. Among the factors that may increase the risk for NSF are repeated or higher than recommended doses of a GBCA and the degree of renal impairment at the time of exposure. Record the specific GBCA and the dose administered to a patient. When administering Omniscan, do not exceed the recommended dose and allow a sufficient period of time for elimination of the drug prior to any readministration

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


Anaphylactoid and anaphylactic reactions, with cardiovascular, respiratory and/or cutaneous manifestations, resulting in death have occurred. Personnel trained in resuscitation techniques and resuscitation equipment should be present prior to Omniscan administration. If a hypersensitivity reaction occurs, stop Omniscan Injection and immediately begin appropriate therapy. Observe patients closely, particularly those with a history of drug reactions, asthma, allergy or other hypersensitivity disorders, during and up to several hours after Omniscan Injection.

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


For more Drug Warnings (Complete) data for GADODIAMIDE (24 total), please visit the HSDB record page.


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
GADODIAMIDE
5.2.2 FDA UNII
84F6U3J2R6
5.2.3 Pharmacological Classes
Paramagnetic Contrast Agent [EPC]; Magnetic Resonance Contrast Activity [MoA]
5.3 ATC Code

V - Various

V08 - Contrast media

V08C - Magnetic resonance imaging contrast media

V08CA - Paramagnetic contrast media

V08CA03 - Gadodiamide


5.4 Absorption, Distribution and Excretion

The objective of this study was to determine the gadolinium (Gd) concentration remaining in human bone tissue after administration of standard clinical doses of 2 Gd-based contrast agents: ProHance and Omniscan. After administration of 0.1 mmol/kg of Gd chelate to patients undergoing hip replacement surgery, bone specimens were collected and analyzed, and compared with an age-matched control population without a history of Gd chelate administration. Bone specimens were collected fresh, refrigerated, and subsequently frozen. After grinding and freeze-drying, tissue digestion was performed using Teflon bombs and concentrated nitric acid. A method for analysis of Gd in bone specimens was developed and validated using inductively coupled plasma mass spectroscopy (ICP-MS). Results were compared with a previous study using a different technique for analysis of the same tissue specimens. Tissue retention was 1.77+/-0.704 microg Gd/g bone (n=9) for Omniscan and 0.477+/-0.271 microg Gd/g bone (n=10) for ProHance measured by ICP-MS. These findings confirmed results from the previous ICP-AES study. Omniscan (Gd[DTPA-BMA]) left approximately 4 times (previous study 2.5 times) more Gd behind in bone than did ProHance (Gd[HP-DO3A]).

PMID:16481910 White GW et al; Invest Radiol 41 (3): 272-8 (2006)


Twenty-seven patients--nine with severely reduced renal function (glomerular filtration rate, 2-10 mL/min), nine undergoing hemodialysis, and nine undergoing continuous ambulatory peritoneal dialysis--were followed up for 5, 8, and 22 days, respectively, after receiving gadodiamide injection (0.1 mmol per kilogram body weight). Gadodiamide injection caused no changes in renal function. In patients with severely reduced renal function, the elimination half-life of gadodiamide injection was prolonged (34.3 hours +/- 22.9) compared with data in healthy volunteers (1.3 hours +/- 0.25). An average of 65% of the gadodiamide injected was eliminated during a hemodialysis session. After 22 days of continuous ambulatory peritoneal dialysis, 69% of the total amount of gadodiamide was excreted; this reflects the low peritoneal clearance. In all patients, no metabolism or transmetallation of gadodiamide was found. ...

PMID:9653466 Joffe P et al; Acad Radiol 5 (7): 491-502 (1998)


The pharmacokinetic behavior of gadodiamide was consistent with its extracellular distribution. ... Gadodiamide was shown to be excreted rapidly, primarily through the kidneys. In rats, 94% of the administered dose was excreted in the urine within the first 24 hours after administration. Approximately 1% to 4% appeared in the feces during the same period.

PMID:8486501 Harpur ES et al; Invest Radiol 28 (Suppl 1): S28-43 (1993)


... /In rats/ following iv dosing of gadodiamide (NaCa DTPA-BMA) (0.015 mmol/kg) in a (14)C-labeled form, plasma concentrations of the drug declined rapidly with an elimination half-live of 0.31 hr, a distribution volume of 244 mL/kg and a plasma clearance of 9.2 mL/min/kg. These results demonstrate that NaCa DTPA-BMA distributes into the extracellular fluid compartment and is renally excreted via glomerular filtration. Of the dose of radioactivity given, 86.6% was excreted in urine by 4 hr after injection, and 95.3% in urine and 3.3% in feces by 120 hr. ...

PMID:8821523 Okazaki O et al; Arzneimittelforschung 46 (1): 79-83 (1996)


For more Absorption, Distribution and Excretion (Complete) data for GADODIAMIDE (10 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

In addition, experiments were done /in rats/ to clarify the in vivo metabolism of gadodiamide (NaCa DTPA-BMA). Results show small quantities of transchelated forms of NaCa DTPA-BMA in urine. HPLC analysis demonstrated these metabolites were the Zn and Cu forms of the drug, resulting from displacement of the Ca ion in the NaCa DTPA-BMA molecule by endogeneous Zn or Cu. Further analyses by HPLC and ICP-AES demonstrate that the unchanged parent drug, the Zn and the Cu forms occur in relative quantities of approximately 92%, 7%, and 1%, respectively. This demonstrates that the Ca ion in caldiamide sodium can be replaced by Zn or Cu ions in vivo, but only to a small extent.

PMID:8821523 Okazaki O et al; Arzneimittelforschung 46 (1): 79-83 (1996)


5.6 Biological Half-Life

... /In rats/ following iv dosing of gadodiamide (NaCa DTPA-BMA) (0.015 mmol/kg) in a (14)C-labeled form, plasma concentrations of the drug declined rapidly with an elimination half-live of 0.31 hr ...

PMID:8821523 Okazaki O et al; Arzneimittelforschung 46 (1): 79-83 (1996)


The pharmacokinetic behavior of gadodiamide was consistent with its extracellular distribution. Its half-life in rats, rabbits, and monkeys was short, 18, 38, and 75 minutes, respectively.

PMID:8486501 Harpur ES et al; Invest Radiol 28 Suppl 1:S28-43 (1993)


The pharmacokinetics of intravenously administered gadodiamide in normal subjects conforms to an open, two-compartment model with mean distribution and elimination half-lives (reported as mean + or - SD) of 3.7 + or - 2.7 minutes and 77.8 + or - 16 minutes, respectively.

NIH; DailyMed. Current Medication Information for Omniscan (Gadodiamide) Injection (Revised: September 2013). Available from, as of October 27, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a


... The average half-time of gadodiamide was 1.93 hr (SD 0.55) /in thirteen hemodialysis patients with abdominal disease receiving iv gadodiamide (0.1 mmol/kg body weight)/.

PMID:16958426 Saitoh T et al; Radiat Med 24 (6): 445-51 (2006)


Twenty-seven patients--nine with severely reduced renal function (glomerular filtration rate, 2-10 mL/min), nine undergoing hemodialysis, and nine undergoing continuous ambulatory peritoneal dialysis--were followed up for 5, 8, and 22 days, respectively, after receiving gadodiamide injection (0.1 mmol per kilogram body weight). Gadodiamide injection caused no changes in renal function. In patients with severely reduced renal function, the elimination half-life of gadodiamide injection was prolonged (34.3 hours +/- 22.9) compared with data in healthy volunteers (1.3 hours +/- 0.25). ...

PMID:9653466 Joffe P et al; Acad Radiol 5 (7): 491-502 (1998)


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