関: gadolinium DTPA、gadopentetic acid、Magnevist、meglumine gadopentetate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/24 08:40:31」(JST)

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Gadopentetic acid is one of the trade names for a gadolinium-based MRI contrast agent, 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 and introduced as the first MRI contrast agent in 1987. 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.

A bottle of Magnevist contrast agent.

Marketed as Magnevist by Bayer Schering Pharma, it was the first intravenous contrast agent to become available for clinical use, and is in widespread use around the world. Similar contrast agents are Magnetol manufactured by Soreq, Dotarem (gadoterate) Guerbet, MultiHance (gadobenate dimeglumine) and ProHance (gadoteridol) manufactured by Bracco, Omniscan (gadodiamide) manufactured by GE Healthcare, and OptiMARK (gadoversetamide) manufactured by Mallinckrodt.

Gadolinium based agents may cause a toxic reaction known as nephrogenic systemic fibrosis (NSF) in patients with severe kidney problems.^[1]^[2]

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.^[3]^[4]

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.^[5] 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.^[6]

References

^ Murphy KJ, Brunberg JA, Cohan RH (1996). "Adverse reactions to gadolinium contrast media: a review of 36 cases". American Journal of Roentgenology. 167 (4): 847–849. doi:10.2214/ajr.167.4.8819369. PMID 8819369.
^ H.S. Thomsen; S.K. Morcos; P. Dawson (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. 61 (11): 905–906. doi:10.1016/j.crad.2006.09.003. PMID 17018301.
^ Bashir A, Gray ML, Boutin RD, Burstein D. Glycosaminoglycan in articular cartilage: in vivo assessment with delayed Gd(DTPA)(2-)-enhanced MR imaging. Radiology. Nov 1997;205(2) 551–558.
^ Bashir A, Gray ML, Hartke J, Burstein D. Nondestructive imaging of human cartilage glycosaminoglycan concentration by MRI. Magn Reson Med. May 1999;41(5) 857–865.
^ A. Dean Sherry, Peter Caravan, Robert E. Lenkinski "Primer on Gadolinium Chemistry" J. Magnetic Resonance 2009, volume 30, p1240–1248. doi:10.1002/jmri.21966
^ Caravan, Peter; Ellison, Jeffrey J.; McMurry, Thomas J.; Lauffer, Randall B. (1999). "Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and Applications". Chem. Revs. 99 (9): 2293–2342. doi:10.1021/cr980440x. PMID 11749483.

External links

Bayer Healthcare Pharmaceuticals page on Magnevist (for US)
Bayer Schering Pharma global Magnevist Website
"Gadopentetate Dimeglumine". Magnetic Resonance—Technology Information Portal. Retrieved 2006-03-27.

UpToDate Contents

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1. 進行した腎不全における腎性全身性線維症／腎性線維化性皮膚症 nephrogenic systemic fibrosis nephrogenic fibrosing dermopathy in advanced renal failure
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English Journal

Enhanced conjugation stability and blood circulation time of macromolecular gadolinium-DTPA contrast agent.

Jenjob R1, Kun N2, Ghee JY3, Shen Z4, Wu X4, Cho SK5, Lee DH6, Yang SG7.
Materials science & engineering. C, Materials for biological applications.Mater Sci Eng C Mater Biol Appl.2016 Apr 1;61:659-64. doi: 10.1016/j.msec.2016.01.008. Epub 2016 Jan 7.
In this study, we prepared macromolecular MR T1 contrast agent: pullulan-conjugated Gd diethylene triamine pentaacetate (Gd-DTPA-Pullulan) and estimated residual free Gd(3+), chelation stability in competition with metal ions, plasma and tissue pharmacokinetics, and abdominal MR contrast on rats. Re
PMID 26838894

Investigating the stability of gadolinium based contrast agents towards UV radiation.

Birka M1, Roscher J1, Holtkamp M1, Sperling M2, Karst U3.
Water research.Water Res.2016 Mar 15;91:244-50. doi: 10.1016/j.watres.2016.01.012. Epub 2016 Jan 11.
Since the 1980s, the broad application of gadolinium(Gd)-based contrast agents for magnetic resonance imaging (MRI) has led to significantly increased concentrations of Gd in the aqueous environment. Little is known about the stability of these highly polar xenobiotics under environmental conditions
PMID 26802476

Comparison of tissue distribution, phrenic nerve involvement, and epidural spread in standard- vs low-volume ultrasound-guided interscalene plexus block using contrast magnetic resonance imaging: a randomized, controlled trial†.

Stundner O1, Meissnitzer M2, Brummett CM3, Moser S3, Forstner R2, Koköfer A4, Danninger T4, Gerner P4, Kirchmair L5, Fritsch G4.
British journal of anaesthesia.Br J Anaesth.2016 Mar;116(3):405-12. doi: 10.1093/bja/aev550.
BACKGROUND: Ultrasound guidance allows for the use of much lower volumes of local anaesthetics for nerve blocks, which may be associated with less aberrant spread and fewer complications. This randomized, controlled study used contrast magnetic resonance imaging to view the differential-volume local
PMID 26865133

Japanese Journal

Evaluation of Liver Fibrosis Using Texture Analysis on Combined-Contrast-Enhanced Magnetic Resonance Images at 3.0T

BioMed Research International 2015, 2015
NAID 120005745652

Incidence and Severity of Acute Adverse Reactions to Four Different Gadolinium-based MR Contrast Agents

Magnetic Resonance in Medical Sciences 13(1), 1-6, 2014
NAID 130003392983

Estimation of Perilymph Enhancement after Intratympanic Administration of Gd-DTPA by Fast T1-mapping with a Dual Flip Angle 3D Spoiled Gradient Echo Sequence

Magnetic resonance in medical sciences : MRMS 12(3), 223-228, 2013-09-01
NAID 10031201760

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★リンクテーブル★

リンク元	「ガドペンテト酸メグルミン」「ガドペンテト酸ジメグルミン」「Magnevist」「gadolinium DTPA」「gadopentetic acid」
関連記事	「dimeglumine」

「ガドペンテト酸メグルミン」

Gadopentetic acid
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pharmacokinetic data
Biological half-life	Distribution half life 12 minutes, elimination half 100 minutes
Identifiers
CAS Number	86050-77-3
ATC code	V08CA01 (WHO)
PubChem	CID 55466
DrugBank	DB00789
ChemSpider	50087
UNII	RH248G8V27
KEGG	D01707
ChEBI	CHEBI:31797
ChEMBL	CHEMBL1200431
Chemical data
Formula	C14H18GdN3O10
Molar mass	545.56 g·mol−1
	SMILES [Gd+3].[O-]C(=O)CN(CCN(CC(=O)O)CC([O-])=O)CCN(CC([O-])=O)CC(=O)O.O[C@H]([C@@H](O)CNC)[C@H](O)[C@H](O)CO.O[C@@H](CNC)[C@@H](O)[C@H](O)[C@H](O)CO ;
	InChI InChI=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 ; Key:LGMLJQFQKXPRGA-VPVMAENOSA-K ;
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