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Revision as of 14:46, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,077 edits Saving copy of the {{drugbox}} taken from revid 456631572 of page Gadodiamide for the Chem/Drugbox validation project (updated: 'ChEMBL').		Latest revision as of 07:53, 6 May 2024 edit Kku (talk | contribs)Extended confirmed users115,739 editsm link contrast agent
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			{{Short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
			{{Use dmy dates|date=August 2021}}
	{{Drugbox		{{Drugbox
	| Verifiedfields = changed		| Verifiedfields = changed
		⚫	| verifiedrevid = 461115819
	| Watchedfields = changed
⚫	| verifiedrevid = 399932728
⚫	| IUPAC_name = gadolinium(III) 5,8-''bis''(carboxylatomethyl)-2--10-oxo-2,5,8,11-tetraazadodecane-1-carboxylate hydrate
	| image = Gadodiamide.png		| image = Gadodiamide.png
	| width = 250px		| width = 250
			| alt =
	| image2 = Gadodiamide2.png
	| width2 = 250px
			<!-- Clinical data -->
			| pronounce =
		⚫	| tradename = Omniscan
		⚫	| Drugs.com = {{drugs.com|CONS|gadodiamide-intravenous}}
			| MedlinePlus =
			| DailyMedID = Gadodiamide
		⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			| pregnancy_AU_comment =
		⚫	| pregnancy_category=
		⚫	| routes_of_administration = ]
			| class =
		⚫	| ATC_prefix = V08
		⚫	| ATC_suffix = CA03
			| ATC_supplemental =
	<!--Clinical data-->		<!-- Legal status -->
⚫	| tradename =
⚫	| Drugs.com = {{drugs.com|CONS|gadodiamide}}
⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	| pregnancy_US = C<!-- A / B / C / D / X -->
⚫	| pregnancy_category =
	| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->		| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
	| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->		| legal_CA = Rx-only
			| legal_CA_comment = <ref>{{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}}</ref>
	| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->		| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
	| legal_US = Rx-only <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->		| legal_US = Rx-only
			| legal_US_comment = <ref name="Omniscan FDA label">{{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}}</ref>
⚫	| legal_status =
			| legal_EU = Rx-only
⚫	| routes_of_administration = ]
			| legal_EU_comment = <ref>{{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}}</ref>
		⚫	| legal_status =
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
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	| metabolism = not metabolized		| metabolism = not metabolized
	| elimination_half-life = 77.8 minutes		| elimination_half-life = 77.8 minutes
	| excretion = ]		| excretion = ]
	<!--Identifiers-->		<!--Identifiers-->
	| CASNo_Ref = {{cascite|correct|CAS}}		| CAS_number_Ref = {{cascite|changed|CAS}}
			| CAS_number = 131410-48-5
	| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 122795-43-1		| CAS_supplemental = <br />{{CAS|122795-43-1}} (hydrate)
⚫	| ATC_prefix = V08
⚫	| ATC_suffix = CA03
	| PubChem = 153921		| PubChem = 153921
	| DrugBank_Ref = {{drugbankcite|changed|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB00225		| DrugBank = DB00225
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 84F6U3J2R6		| UNII = 84F6U3J2R6
	| KEGG_Ref = {{keggcite|changed|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D01645		| KEGG = D01645
	| ChEBI_Ref = {{ebicite|changed|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 37333		| ChEBI = 37333
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 1200346 -->		| ChEMBL = 1200346
	| chemical_formula =
			<!--Chemical data-->
⚫	| C=16 | H=28 | Gd=1 | N=5 | O=9
		⚫	| IUPAC_name = gadolinium(III) 5,8-''bis''(carboxylatomethyl)-2--10-oxo-2,5,8,11-tetraazadodecane-1-carboxylate hydrate
	| molecular_weight = 591.672g/mol
		⚫	| C=16 | H=28 | Gd=1 | N=5 | O=9
	| smiles = .C(=O)CN(CC(=O)NC)CCN(CCN(CC()=O)CC(=O)NC)CC()=O		| smiles = .C(=O)CN(CC(=O)NC)CCN(CCN(CC()=O)CC(=O)NC)CC()=O
	| InChI = 1/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
	| InChIKey = HZHFFEYYPYZMNU-DFZHHIFOAX
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| 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		| 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
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	| synonyms = <small>2-amino]acetate; gadolinium(+3) cation</small>		| synonyms = <small>2-amino]acetate; gadolinium(+3) cation</small>
	}}		}}
			'''Gadodiamide''', sold under the brand name '''Omniscan''', is a ] (GBCA), used in ] (MRI) procedures to assist in the visualization of blood vessels.
			== Medical uses ==
			{{further|MRI contrast agent}}
			]
			Gadodiamide is a ] used for cranial and spinal ] (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 ] (CNS). It crosses intact the ].<ref>{{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 | year = 2020 | doi = 10.1002/jmri.27124 | pmid = 32246802 | pmc = 7687192 }}</ref>
			== Adverse effects ==
			Gadodiamide is one of the main GBCA associated with ] (NSF), a toxic reaction occurring in some people with ].<ref>{{cite journal | vauthors = Ibrahim MA, Hazhirkarzar B, Dublin AB | title = Magnetic Resonance Imaging (MRI), Gadolinium | journal = StatPearls | location = Treasure Island (FL) | publisher = StatPearls Publishing | date = January 2018 | pmid = 29494094 }}</ref> No cases have been seen in people with normal kidney function.<ref>{{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 = 324–36 | year = 2008 | pmid = 18587720 }}</ref>
			A 2015 study found ] deposited in the brain tissue of people who had received gadodiamide.<ref name=Med2015>{{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}}</ref> Other studies using ] ] found most of the deposit remained at least 2 years after an injection and deposit also in individuals with no kidney issues.
			] studies found it to be ].<ref>{{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/ }}</ref>
			An Italian task force recommended that breastfeeding mothers precautionally avoid any ], such as gadodiamide, that has been associated with nephrogenic systemic fibrosis.<ref>{{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 | display-authors = 6 | 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 = 2012–22 | date = August 2014 | pmid = 24838733 | doi = 10.1007/s00330-014-3198-6 | s2cid = 24502257 }}</ref>
			== Society and culture ==
			Gadodiamide was suspended along with ] (Magnevist) by the ] in 2017.<ref>{{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}}</ref>
			== References ==
			{{reflist}}
			{{Contrast media}}
			{{Portal bar | Medicine}}
			]
			]
			]