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Identification
Name Gadobenate Dimeglumine
Accession Number DB00743 (APRD00989)
Type small molecule
Groups approved
Description

Gadobenate Dimeglumine is an MRI contrast agent used primarily for MR imaging of the liver. It can also be used for visualizing the CNS and heart. In contrast to conventional extracellular fluid contrast agents, gadobenate dimeglumine is characterized by a weak and transient binding capacity to serum proteins. This binding leads to an increased relaxivity of gadobenate dimeglumine and, consequently, to a considerably increased signal intensity over that of other agents.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
Gadobenic acid
Salts Not Available
Brand names
Name Company
Gd-BOPTA
Gd-BOPTA/Dimeg
Multihance
Multihance Multipack
Brand mixtures Not Available
Categories
  • Contrast Media
CAS number 113662-23-0
Weight Average: 1058.15
Monoisotopic: 1058.317829604
Chemical Formula C36H62GdN5O21
InChI Key InChIKey=OCDAWJYGVOLXGZ-VPVMAENOSA-K
InChI
InChI=1S/C22H31N3O11.2C7H17NO5.Gd/c26-18(27)10-23(6-7-24(11-19(28)29)12-20(30)31)8-9-25(13-21(32)33)17(22(34)35)15-36-14-16-4-2-1-3-5-16;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1
Plain Text
IUPAC Name
gadolinium(3+) ion bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate
SMILES
[Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CCN(CCN(CC(O)=O)C(COCC1=CC=CC=C1)C([O-])=O)CC([O-])=O)CC([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Amino Acids
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Anions
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Amino Alcohols
  • Aromatic compounds
  • Amino Acids
  • Cations
Pharmacology
Indication Gadobenate Dimeglumine is an MRI contrast agent used primarily for MR imaging of the liver. It can also be used for MRI of the heart, as well as and central nervous system in adults to visualize lesions with abnormal brain vascularity or abnormalities in the blood brain barrier, the brain, spine, or other associated tissues.
Pharmacodynamics Gadobenate dimeglumine shares the pharmacokinetic properties of the ECF contrast agent gadopentetate dimeglumine; however, gadobenate differs in that is also selectively taken-up by hepatocytes and excreted via the bile (up to 5% of dose). The elimination half-life of gadobenate dimeglumine is approximately 1 hour. It is not metabolized.
Mechanism of action Based on the behavior of protons when placed in a strong magnetic field, which is interpreted and transformed into images by magnetic resonance (MR) instruments. Paramagnetic agents have unpaired electrons that generate a magnetic field about 700 times larger than the proton's field, thus disturbing the proton's local magnetic field. When the local magnetic field around a proton is disturbed, its relaxation process is altered. MR images are based on proton density and proton relaxation dynamics. MR instruments can record 2 different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and the T2 (spin-spin or transverse relaxation time). In magnetic resonance imaging (MRI), visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in the T2. When placed in a magnetic field, Gadobenate Dimeglumine shortens both the T1 and the T2 relaxation times in tissues where it accumulates. At clinical doses, Gadobenate Dimeglumine primarily affects the T1 relaxation time, thus producing an increase in signal intensity. Gadobenate Dimeglumine does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in central nervous system (CNS) lesions that have not caused an abnormal blood-brain barrier (e.g., cysts, mature post-operative scars).
Absorption Not Available
Volume of distribution Not Available
Protein binding Plasma protein binding is low, weak, and transient.
Metabolism
Not metabolized.
Route of elimination Gadobenate ion is eliminated predominately via the kidneys, with 78% to 96% of an administered dose recovered in the urine.
Half life 1 hour
Clearance
  • 0.093 +/- 0.010 L/hr/kg [healthy male subjects receiving 3 single-dose IV administration with doses from 0.005-0.4 mmol/kg]
Toxicity Gadolinium-based radiocontrast agents like gadobenate dimeglumine are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bracco diagnostics inc
Packagers
Dosage forms
Form Route Strength
Solution Intravenous
Prices
Unit description Cost Unit
Multihance 529 mg/ml vial 6.87 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 4916246 1995-04-10 2012-04-10
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
logP -4.1 ChemAxon
pKa (strongest acidic) 0.085 ChemAxon
pKa (strongest basic) 9.58 ChemAxon
physiological charge -4 ChemAxon
hydrogen acceptor count 14 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 213.94 ChemAxon
rotatable bond count 32 ChemAxon
refractivity 154.36 ChemAxon
polarizability 48.51 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. de Haen C, Cabrini M, Akhnana L, Ratti D, Calabi L, Gozzini L: Gadobenate dimeglumine 0.5 M solution for injection (MultiHance) pharmaceutical formulation and physicochemical properties of a new magnetic resonance imaging contrast medium. J Comput Assist Tomogr. 1999 Nov;23 Suppl 1:S161-8. Pubmed
  2. Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. Pubmed
  3. Vogl TJ, Pegios W, McMahon C, Balzer J, Waitzinger J, Pirovano G, Lissner J: Gadobenate dimeglumine—a new contrast agent for MR imaging: preliminary evaluation in healthy volunteers. AJR Am J Roentgenol. 1992 Apr;158(4):887-92. Pubmed
  4. Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. Pubmed
  5. Clement O, Siauve N, Cuenod CA, Vuillemin-Bodaghi V, Leconte I, Frija G: Mechanisms of action of liver contrast agents: impact for clinical use. J Comput Assist Tomogr. 1999 Nov;23 Suppl 1:S45-52. Pubmed
External Links
Resource Link
PubChem Compound 6918204 Link_out
PubChem Substance 46506805 Link_out
ChemSpider 170831 Link_out
Therapeutic Targets Database DAP001225 Link_out
PharmGKB PA164745426 Link_out
Drug Product Database 2248302 Link_out
ATC Codes
  • V08CA08
AHFS Codes
  • 92:00.00
PDB Entries Not Available
FDA label show (247 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Carriers

1. Serum albumin

Actions: binder

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Port M, Corot C, Violas X, Robert P, Raynal I, Gagneur G: How to compare the efficiency of albumin-bound and nonalbumin-bound contrast agents in vivo: the concept of dynamic relaxivity. Invest Radiol. 2005 Sep;40(9):565-73. Pubmed
  2. Wendland MF, Saeed M, Lauerma K, Derugin N, Mintorovitch J, Cavagna FM, Higgins CB: Alterations in T1 of normal and reperfused infarcted myocardium after Gd-BOPTA versus GD-DTPA on inversion recovery EPI. Magn Reson Med. 1997 Mar;37(3):448-56. Pubmed
  3. Cavagna FM, Maggioni F, Castelli PM, Dapra M, Imperatori LG, Lorusso V, Jenkins BG: Gadolinium chelates with weak binding to serum proteins. A new class of high-efficiency, general purpose contrast agents for magnetic resonance imaging. Invest Radiol. 1997 Dec;32(12):780-96. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19