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Revision as of 12:58, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 472775067 of page Gadopentetic_acid for the Chem/Drugbox validation project (updated: 'ChEMBL').  Latest revision as of 06:00, 13 July 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,333 edits infobox, links 
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{{Short description|Complex of gadolinium by DTPA}}
{{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
| Watchedfields = changed
| verifiedrevid = 458290542 | verifiedrevid = 476997570
| image = Gd(DTPA)(aq)2-.png | image = Gd(DTPA)(aq)2-.png
| USAN = gadopentetate dimeglumine

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Magnevist
| Drugs.com = {{drugs.com|CDI|gadopentetate_dimeglumine}} | Drugs.com = {{drugs.com|CDI|gadopentetate_dimeglumine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_category =
| pregnancy_US = <!-- A / B / C / D / X -->
⚫ | routes_of_administration = ]
⚫ | pregnancy_category =
| ATC_prefix = V08
⚫ | ATC_suffix = CA01
⚫ | ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=] | date=7 July 2016 | 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=13 July 2024}}</ref>
| legal_UK = <!-- GSL / P / POM / CD --> | legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only --> | legal_US = Rx-only
| legal_US_comment =<ref name="Magnevist FDA label">{{cite web | title=Magnevist- gadopentetate dimeglumine injection | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=be234024-ed43-404e-a40e-a3c1572a9726 | access-date=29 August 2021}}</ref>
⚫ | legal_status =
| legal_EU = Rx-only
⚫ | routes_of_administration =
| legal_EU_comment =<ref>{{cite web | date = 14 January 2021 | url = https://www.ema.europa.eu/documents/psusa/gadopentetic-acid-list-nationally-authorised-medicinal-products-psusa/00001504/202004_en.pdf | title = List of nationally authorised medicinal products: Gadopentetic acid | work = Europeans Medicines Agency }}</ref>
⚫ | legal_status =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = Distribution half life 12 minutes, elimination half 100 minutes | elimination_half-life = Distribution half-life 12 minutes, elimination half-life 100 minutes
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 86050-77-3 | CAS_number = 86050-77-3
| ATC_prefix = V08 | PubChem = 6857474
⚫ | ATC_suffix = CA01
⚫ | ATC_supplemental =
| PubChem = 55466
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00789 | DrugBank = DB00789
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| ChEBI = 31797 | ChEBI = 31797
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1200431 --> | ChEMBL = 1200431

⚫ | C=28 | H=54 | Gd=1 | N=5 | O=20
<!--Chemical data-->
| molecular_weight =
⚫ | C=14 | H=18 | Gd=1 | N=3 | O=10
| smiles = .C(=O)CN(CCN(CC(=O)O)CC()=O)CCN(CC()=O)CC(=O)O.O((O)CNC)(O)(O)CO.O(CNC)(O)(O)(O)CO | smiles = .C(=O)CN(CCN(CC(=O)O)CC()=O)CCN(CC()=O)CC(=O)O.O((O)CNC)(O)(O)CO.O(CNC)(O)(O)(O)CO
| InChI = 1/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1
| InChIKey = LGMLJQFQKXPRGA-TTXANEAOBX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1 | StdInChI = 1S/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LGMLJQFQKXPRGA-VPVMAENOSA-K | StdInChIKey = LGMLJQFQKXPRGA-VPVMAENOSA-K
|drug_name=|alt=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}}
}}

'''Gadopentetic acid''', sold under the brand name '''Magnevist''', is a ]-based ].<ref name="Magnevist FDA label" />

It is usually administered as a salt of a complex of gadolinium with ] (''d''iethylene''t''riamine''p''ent''a''cetate) with the chemical formula A<sub>2</sub>; when cation A is the protonated form of the ] ] the salt goes under the name "gadopentetate dimeglumine". It was described in 1981 by ] and colleagues<ref>{{Cite patent | country = US | number = 5021236 | url=https://patents.google.com/patent/US5021236|title = Method of enhancing NMR imaging using chelated paramagnetic ions bound to biomolecules}}</ref> and introduced as the first MRI ] in 1987 by the ]. It is used to assist imaging of blood vessels and of inflamed or diseased tissue where the blood vessels become "leaky". It is often used when viewing ] ]s with abnormal ] or abnormalities in the ]. It is usually injected intravenously. Gd-DTPA is classed as an acyclic, ionic gadolinium contrast medium. Its ] property reduces the ] ] (and to some extent the T2 and T2* relaxation times) in ], which is the source of its clinical utility.

]

Gadolinium based agents may cause a toxic reaction known as ] (NSF) in patients with severe kidney problems.<ref name="murphy">{{cite journal | vauthors = Murphy KJ, Brunberg JA, Cohan RH | title = Adverse reactions to gadolinium contrast media: a review of 36 cases | journal = AJR. American Journal of Roentgenology | volume = 167 | issue = 4 | pages = 847–849 | date = October 1996 | pmid = 8819369 | doi = 10.2214/ajr.167.4.8819369 | doi-access = free }}</ref><ref name="thomsen">{{cite journal | vauthors = Thomsen HS, Morcos SK, Dawson P | title = Is there a causal relation between the administration of gadolinium based contrast media and the development of nephrogenic systemic fibrosis (NSF)? | journal = Clinical Radiology | volume = 61 | issue = 11 | pages = 905–906 | date = November 2006 | pmid = 17018301 | doi = 10.1016/j.crad.2006.09.003 }}</ref>

Compared to other gadolinium-based MRI contrast agents, Gadopentetate dimeglumine (Gd-DTPA2-) ] allow ]. The unique charge characteristic of this complex allows researchers to inversely measure ]s as they are related to the concentration of ] aggregates and charged ] side chains in ].<ref>{{cite journal | vauthors = Bashir A, Gray ML, Boutin RD, Burstein D | title = Glycosaminoglycan in articular cartilage: in vivo assessment with delayed Gd(DTPA)(2-)-enhanced MR imaging | journal = Radiology | volume = 205 | issue = 2 | pages = 551–558 | date = November 1997 | pmid = 9356644 | doi = 10.1148/radiology.205.2.9356644 }}</ref><ref>{{cite journal | vauthors = Bashir A, Gray ML, Hartke J, Burstein D | title = Nondestructive imaging of human cartilage glycosaminoglycan concentration by MRI | journal = Magnetic Resonance in Medicine | volume = 41 | issue = 5 | pages = 857–865 | date = May 1999 | pmid = 10332865 | doi = 10.1002/(sici)1522-2594(199905)41:5<857::aid-mrm1>3.0.co;2-e | s2cid = 22939233 | doi-access = free }}</ref>

==Chemical structure and mode of action==
In the complex of Gd<sup>3+</sup> and DTPA<sup>5−</sup> the gadolinium ion is 9-coordinate, surrounded by the 3 nitrogen atoms and 5 oxygen atoms from the carboxylate groups. The ninth coordination site is occupied by a water molecule.{{cite journal | vauthors = Sherry AD, Caravan P, Lenkinski RE | title = Primer on gadolinium chemistry | journal = Journal of Magnetic Resonance Imaging | volume = 30 | issue = 6 | pages = 1240–1248 | date = December 2009 | pmid = 19938036 | pmc = 2853020 | doi = 10.1002/jmri.21966 }} This water molecule is ] and exchanges rapidly with water molecules in the immediate vicinity of the gadolinium complex. The gadolinium ion has 7 unpaired electrons with parallel spins and is strongly ] with an <sup>8</sup>S electronic ground state. The ] of the water molecules is affected by their intermittent binding to the paramagnetic centre. This alters their MRI properties and enables contrast enhancement to be achieved.<ref>{{cite journal | vauthors = Caravan P, Ellison JJ, McMurry TJ, Lauffer RB | title = Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and Applications | journal = Chemical Reviews | volume = 99 | issue = 9 | pages = 2293–2352 | date = September 1999 | pmid = 11749483 | doi = 10.1021/cr980440x }}</ref>

== Concerns ==
Gadolinium is highly toxic and the accumulation of gadolinium in the brain has become a concern. The EU banned linear chelates 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><ref>{{Cite web|title=EU pulls gadolinium contrast agents over deposition concerns|url=https://www.radiologybusiness.com/topics/policy/eu-pulls-gadolinium-contrast-agents-over-deposition-concerns|access-date=18 August 2020|website=www.radiologybusiness.com}}</ref>

== References ==
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