Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Gadopentetic acid: Difference between pages

{{Short description|Complex of gadolinium by DTPA}}

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

| Watchedfields = changed

| verifiedrevid = 476997570

| USAN = gadopentetate dimeglumine

| tradename = Magnevist

| pregnancy_category =

| routes_of_administration = [[Intravenous]]

| ATC_prefix = V08

| ATC_suffix = CA01

| ATC_supplemental =

<!-- Legal status -->

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=[[Health Canada]] | 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_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_EU = Rx-only

| 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 =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = Distribution half-life 12 minutes, elimination half-life 100 minutes

| excretion =

| PubChem = 6857474

| ChEMBL = 1200431

<!--Chemical data-->

| C=14 | H=18 | Gd=1 | N=3 | O=10

|drug_name=|alt=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}}

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

It is usually administered as a salt of a complex of gadolinium with [[DTPA]] (''d''iethylene''t''riamine''p''ent''a''cetate) with the chemical formula A₂[Gd(DTPA)(H₂O)]; when cation A is the protonated form of the [[amino sugar]] [[meglumine]] the salt goes under the name "gadopentetate dimeglumine". It was described in 1981 by [[Hanns-Joachim Weinmann]] 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 [[contrast agent]] in 1987 by the [[Schering AG]]. 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 [[intracranial]] [[lesion]]s with abnormal [[blood vessel|vascularity]] or abnormalities in the [[blood–brain barrier]]. It is usually injected intravenously. Gd-DTPA is classed as an acyclic, ionic gadolinium contrast medium. Its [[paramagnetic]] property reduces the [[Spin-lattice relaxation time|T1]] [[Relaxation (NMR)|relaxation time]] (and to some extent the T2 and T2* relaxation times) in [[NMR]], which is the source of its clinical utility.

[[File:Magnevist Bottle.JPG|thumb|left|A bottle of Magnevist contrast agent.]]

Gadolinium based agents may cause a toxic reaction known as [[nephrogenic systemic fibrosis]] (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-) [[chelates]] allow [[Delayed Gadolinium Enhanced Magnetic Resonance Imaging of Cartilage (dGEMRIC)|delayed Gadolinium-enhanced Magnetic Resonance of Cartilage (dGEMRIC)]]. The unique charge characteristic of this complex allows researchers to inversely measure [[spin-lattice relaxation time]]s as they are related to the concentration of [[proteoglycan]] aggregates and charged [[glycosaminoglycan]] side chains in [[articular cartilage]].<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 Gd³⁺ and DTPA⁵⁻ 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 [[labile]] 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 [[paramagnetic]] with an ⁸S electronic ground state. The [[relaxation time]] 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 ==

{{reflist}}

{{Contrast media}}

{{Portal bar | Medicine}}

[[Category:MRI contrast agents]]

[[Category:Organogadolinium compounds]]

[[Category:Withdrawn drugs]]