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Gadopentetic acid

Complex of gadolinium by DTPA

Summary

Complex of gadolinium by DTPA

Field	Value
Verifiedfields	changed
Watchedfields	changed
verifiedrevid	476997570
image	Gd(DTPA)(aq)2-.png
image_class	skin-invert-image
USAN	gadopentetate dimeglumine
<!--Clinical data-->	tradename	Magnevist
Drugs.com
pregnancy_AU
routes_of_administration	Intravenous
ATC_prefix	V08
ATC_suffix	CA01
ATC_supplemental
legal_AU
legal_CA	Rx-only
legal_CA_comment
legal_UK
legal_US	Rx-only
legal_US_comment
legal_EU	Rx-only
legal_EU_comment
legal_status
elimination_half-life	Distribution half-life 12 minutes, elimination half-life 100 minutes
excretion
CAS_number_Ref
CAS_number	86050-77-3
PubChem	6857474
DrugBank_Ref
DrugBank	DB00789
ChemSpiderID_Ref
ChemSpiderID	50087
UNII_Ref
UNII	RH248G8V27
KEGG_Ref
KEGG	D01707
ChEBI_Ref
ChEBI	31797
ChEMBL_Ref
ChEMBL	1200431
<!--Chemical data-->	C	14
H	20
Gd	1
N	3
O	10
smiles	[Gd+3].[O-]C(=O)CN(CCN(CC(=O)O)CC([O-])=O)CCN(CC([O-])=O)CC(=O)O.OC@H C@H C@HCO.OC@@HC@@H C@H C@HCO
StdInChI_Ref
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;21-8-2-4(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);24-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1
StdInChIKey_Ref
StdInChIKey	LGMLJQFQKXPRGA-VPVMAENOSA-K

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

Gadopentetic acid, sold under the brand name Magnevist, is a gadolinium-based MRI contrast agent.

It is usually administered as a salt of a complex of gadolinium with DTPA (diethylenetriaminepentacetate) 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 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 lesions with abnormal 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 T1 relaxation time (and to some extent the T2 and T2* relaxation times) in NMR, which is the source of its clinical utility.

Gadolinium based agents may cause a toxic reaction known as nephrogenic systemic fibrosis (NSF) in patients with severe kidney problems.

Compared to other gadolinium-based MRI contrast agents, Gadopentetate dimeglumine (Gd-DTPA2-) chelates allow delayed Gadolinium-enhanced Magnetic Resonance of Cartilage (dGEMRIC). The unique charge characteristic of this complex allows researchers to inversely measure spin-lattice relaxation times as they are related to the concentration of proteoglycan aggregates and charged glycosaminoglycan side chains in articular cartilage.

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. 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.

Concerns

Gadolinium is highly toxic and the accumulation of gadolinium in the brain has become a concern. The EU banned linear chelates in 2017.

References

(7 July 2016). "Product monograph brand safety updates".
"Magnevist- gadopentetate dimeglumine injection".
(14 January 2021). "List of nationally authorised medicinal products: Gadopentetic acid". Europeans Medicines Agency.
"Method of enhancing NMR imaging using chelated paramagnetic ions bound to biomolecules".
(October 1996). "Adverse reactions to gadolinium contrast media: a review of 36 cases". AJR. American Journal of Roentgenology.
(November 2006). "Is there a causal relation between the administration of gadolinium based contrast media and the development of nephrogenic systemic fibrosis (NSF)?". Clinical Radiology.
(November 1997). "Glycosaminoglycan in articular cartilage: in vivo assessment with delayed Gd(DTPA)(2-)-enhanced MR imaging". Radiology.
(May 1999). "Nondestructive imaging of human cartilage glycosaminoglycan concentration by MRI". Magnetic Resonance in Medicine.
(December 2009). "Primer on gadolinium chemistry". Journal of Magnetic Resonance Imaging.
(September 1999). "Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and Applications". Chemical Reviews.
(14 December 2017). "Gadolinium-containing contrast agents: removal of Omniscan and iv Magnevist, restrictions to the use of other linear agents".
"EU pulls gadolinium contrast agents over deposition concerns".

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

mri-contrast-agents organogadolinium-compounds withdrawn-drugs

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