Gadodiamide

{{Short description|Chemical compound}}

{{Use dmy dates|date=August 2021}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 461115819

| image = Gadodiamide.png

| width = 250

| alt =

| pronounce =

| tradename = Omniscan

| Drugs.com = {{drugs.com|CONS|gadodiamide-intravenous}}

| MedlinePlus =

| DailyMedID = Gadodiamide

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = Intravenous

| class =

| ATC_prefix = V08

| ATC_suffix = CA03

| ATC_supplemental =

| legal_AU =

| legal_CA = Rx-only

| legal_CA_comment = {{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}

| legal_UK =

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Omniscan- gadodiamide injection | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1e9a37e2-f28a-4373-bf0f-3e9b60f42d8a | access-date=29 August 2021}}

| legal_EU = Rx-only

| legal_EU_comment = {{cite web | title = Active substance: gadodiamide | date = 14 January 2021 | work = List of nationally authorised medicinal products | publisher = European Medicine Agency | url = https://www.ema.europa.eu/documents/psusa/gadodiamide-list-nationally-authorised-medicinal-products-psusa/00001503/202004_en.pdf}}

| legal_status =

| bioavailability =

| protein_bound = negligible

| metabolism = not metabolized

| elimination_half-life = 77.8 minutes

| excretion = Kidney

| CAS_number_Ref = {{cascite|changed|CAS}}

| CAS_number = 131410-48-5

| CAS_supplemental =
{{CAS|122795-43-1}} (hydrate)

| PubChem = 153921

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00225

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 135661

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 84F6U3J2R6

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01645

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 37333

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1200346

| IUPAC_name = gadolinium(III) 5,8-bis(carboxylatomethyl)-2-[2-(methylamino)-2-oxoethyl]-10-oxo-2,5,8,11-tetraazadodecane-1-carboxylate hydrate

| C=16 | H=28 | Gd=1 | N=5 | O=9

| smiles = [Gd+3].[O-]C(=O)CN(CC(=O)NC)CCN(CCN(CC([O-])=O)CC(=O)NC)CC([O-])=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HZHFFEYYPYZMNU-UHFFFAOYSA-K

| synonyms = 2-[bis[2-(carboxylatomethyl-(methylcarbamoylmethyl)amino)ethyl]amino]acetate; gadolinium(+3) cation

}}

Gadodiamide, sold under the brand name Omniscan, is a gadolinium-based MRI contrast agent (GBCA), used in magnetic resonance imaging (MRI) procedures to assist in the visualization of blood vessels.

Medical uses

{{further|MRI contrast agent}}

File:Omniscan nima.JPG

Gadodiamide is a contrast medium used for cranial and spinal magnetic resonance imaging (MRI) and for general MRI of the body after intravenous administration. It provides contrast enhancement and facilitates visualisation of abnormal structures or lesions in various parts of the body including the central nervous system (CNS). It crosses intact the blood brain barrier.{{cite journal | vauthors = Rasschaert M, Weller RO, Schroeder JA, Brochhausen C, Idée JM | title = Retention of Gadolinium in Brain Parenchyma: Pathways for Speciation, Access, and Distribution. A Critical Review | journal = Journal of Magnetic Resonance Imaging | volume = 52 | issue = 5 | pages = 1293–1305 | date = November 2020 | pmid = 32246802 | pmc = 7687192 | doi = 10.1002/jmri.27124 }}

Adverse effects

Gadodiamide is one of the main GBCA associated with nephrogenic systemic fibrosis (NSF), a toxic reaction occurring in some people with kidney problems.{{cite journal | title = Magnetic Resonance Imaging (MRI), Gadolinium | journal = StatPearls [Internet] | date = January 2018 | pmid = 29494094 | publisher = StatPearls Publishing | vauthors = Ibrahim MA, Hazhirkarzar B, Dublin AB }} No cases have been seen in people with normal kidney function.{{cite journal | vauthors = Canavese C, Mereu MC, Aime S, Lazzarich E, Fenoglio R, Quaglia M, Stratta P | title = Gadolinium-associated nephrogenic systemic fibrosis: the need for nephrologists' awareness | journal = Journal of Nephrology | volume = 21 | issue = 3 | pages = 324–336 | year = 2008 | pmid = 18587720 }}

A 2015 study found gadolinium deposited in the brain tissue of people who had received gadodiamide.{{cite news| vauthors = Anderson P |title=Gadolinium Found in Brain Tissue|url=http://www.medscape.com/viewarticle/842107|access-date=14 April 2015|agency=Medscape|date=26 March 2015}} Other studies using post-mortem mass spectrometry found most of the deposit remained at least 2 years after an injection and deposit also in individuals with no kidney issues.

In vitro studies found it to be neurotoxic.{{cite journal | vauthors = Bower DV, Richter JK, von Tengg-Kobligk H, Heverhagen JT, Runge VM | title = Gadolinium-Based MRI Contrast Agents Induce Mitochondrial Toxicity and Cell Death in Human Neurons, and Toxicity Increases With Reduced Kinetic Stability of the Agent | journal = Investigative Radiology | volume = 54 | issue = 8 | pages = 453–463 | date = August 2019 | pmid = 31265439 | doi = 10.1097/RLI.0000000000000567 | s2cid = 164486744 | url = https://boris.unibe.ch/132314/ }}

An Italian task force recommended that breastfeeding mothers precautionally avoid any contrast agent, such as gadodiamide, that has been associated with nephrogenic systemic fibrosis.{{cite journal | vauthors = Cova MA, Stacul F, Quaranta R, Guastalla P, Salvatori G, Banderali G, Fonda C, David V, Gregori M, Zuppa AA, Davanzo R | title = Radiological contrast media in the breastfeeding woman: a position paper of the Italian Society of Radiology (SIRM), the Italian Society of Paediatrics (SIP), the Italian Society of Neonatology (SIN) and the Task Force on Breastfeeding, Ministry of Health, Italy | journal = European Radiology | volume = 24 | issue = 8 | pages = 2012–2022 | date = August 2014 | pmid = 24838733 | doi = 10.1007/s00330-014-3198-6 | s2cid = 24502257 }}

Like other gadolinium-based contrast agents (GBCAs), gadodiamide may cause a range of adverse reactions. The most common include mild symptoms such as nausea, headache, or injection site discomfort. However, rare but serious reactions have been reported.

= Hypersensitivity and anaphylaxis =

Gadodiamide can cause severe allergic or hypersensitivity reactions, including anaphylaxis—a potentially life-threatening condition requiring immediate medical attention and treatment with epinephrine (adrenaline). Post-marketing surveillance and case studies have documented such events in patients who received gadodiamide.{{cite journal | vauthors = Lv M, Zhang X, Hedwig B | title = Phonotactic steering and representation of directional information in the ascending auditory pathway of a cricket | journal = Journal of Neurophysiology | volume = 123 | issue = 3 | pages = 865–875 | date = March 2020 | pmid = 31913780 | doi = 10.1152/jn.00737.2019 | pmc = 7099476 }}

Data from the U.S. FDA Adverse Event Reporting System (FAERS) also list anaphylaxis and other hypersensitivity reactions among the reported adverse effects associated with gadodiamide.{{Cite web |title=FDA Adverse Event Reporting System (FAERS) Public Dashboard |url=https://www.fda.gov/drugs/questions-and-answers-fdas-adverse-event-reporting-system-faers/fda-adverse-event-reporting-system-faers-public-dashboard |publisher=U.S. Food and Drug Administration |access-date=2025-04-04}}

Patients with a known history of allergic reactions to contrast media or other drugs should inform their healthcare provider before undergoing imaging studies with gadodiamide. In high-risk individuals, premedication and pre-screening protocols may be considered to mitigate the risk of severe reactions.

Society and culture

Gadodiamide was suspended along with gadopentetic acid (Magnevist) by the European Medicines Agency in 2017.{{cite web | title=Gadolinium-containing contrast agents: removal of Omniscan and iv Magnevist, restrictions to the use of other linear agents | website=GOV.UK | date=14 December 2017 | url=https://www.gov.uk/drug-safety-update/gadolinium-containing-contrast-agents-removal-of-omniscan-and-iv-magnevist-restrictions-to-the-use-of-other-linear-agents | access-date=29 August 2021}}

References

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Category:MRI contrast agents

Category:Organogadolinium compounds

Category:Withdrawn drugs