関: gadolinium DTPA、gadopentetate dimeglumine、gadopentetic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/26 21:37:14」(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 and 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
2. 肝胆道系のMRI magnetic resonance imaging of the hepatobiliary tract
3. 直腸癌治療前の局所の病期分類評価 pretreatment local staging evaluation for rectal cancer
4. 腎血管性高血圧の診断 establishing the diagnosis of renovascular hypertension

English Journal

Transport of gadolinium- and arsenic-based pharmaceuticals in saturated soil under various redox conditions.

Menahem A1, Dror I2, Berkowitz B1.
Chemosphere.Chemosphere.2016 Feb;144:713-20. doi: 10.1016/j.chemosphere.2015.09.044. Epub 2015 Sep 25.
The release of pharmaceuticals and personal care products (PPCPs) to the soil-water environment necessitates understanding of PPCP transport behavior under conditions that account for dynamic flow and varying redox states. This study investigates the transport of two organometallic PPCPs, Gd-DTPA an
PMID 26408978

Differences in Perilymphatic Space Enhancement and Adverse Inflammatory Reaction after Intratympanic Injection of Two Different Gadolinium Agents: A 9.4-Tesla Magnetic Resonance Imaging Study.

Park M1, Lee HS2, Kim H3, Oh SH4, Lee JH4, Suh MW5.
Hearing research.Hear Res.2016 Jan 12. pii: S0378-5955(15)30009-5. doi: 10.1016/j.heares.2015.10.022. [Epub ahead of print]
PURPOSE: To compare the inner ear enhancement after intratympanic injection of two widely used gadolinium (Gd) agents by 9.4 Tesla micro-magnetic resonance imaging (MRI) and to investigate the effects of Gd on the inner ear.METHODS: Twelve ears of six rats received intratympanic administration of 1/
PMID 26795351

Hepatic Hemangiomas: Factors Associated with Pseudo Washout Sign on Gd-EOB-DTPA-enhanced MR Imaging.

Tateyama A1, Fukukura Y, Takumi K, Shindo T, Kumagae Y, Nakamura F.
Magnetic resonance in medical sciences : MRMS : an official journal of Japan Society of Magnetic Resonance in Medicine.Magn Reson Med Sci.2016 Jan 12;15(1):73-82. doi: 10.2463/mrms.2014-0125. Epub 2015 Sep 4.
PURPOSE: Our study aim was to clarify the characteristics of hemangiomas with pseudo washout sign (PWS) by comparing their features with those of hemangiomas without PWS on gadolinium-ethoxybenzyl-diethylenetriaminepentaacetic acid (Gd-EOB-DTPA)-enhanced magnetic resonance (MR) imaging.METHODS: We e
PMID 26346400

Japanese Journal

Pharmacokinetics of chiral dendrimer-triamine-coordinated Gd-MRI contrast agents evaluated by in Vivo MRI and estimated by in Vitro QCM

Sensors 15(12), 31973-31986, 2015-12-18
NAID 120005756291

Direct Immobilization of Gadolinium Complex on Silica Particles and Their MRI Properties

e-Journal of Surface Science and Nanotechnology 13(0), 42-46, 2015
NAID 130004933832

Interaction Between Iopamidol and Gadopentetate Dimeglumine: An in-vitro Experimental Study of Direct Mixing

Journal of Nippon Medical School 71(2), 120-125, 2004
NAID 130004057262

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★リンクテーブル★

リンク元	「マグネビスト」「gadopentetate dimeglumine」「gadolinium DTPA」「gadopentetic acid」

「マグネビスト」

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
CASRN	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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