You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
NameGadobenic acid
Accession NumberDB00743  (APRD00989)
TypeSmall Molecule

Gadobenic acid (in the form of 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.

Acide gadobenique
Acido gadobenico
Acidum gadobenicum
Gadobenic acid
External Identifiers
  • B 19036
  • B 19036/7
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Multihanceinjection, solution529 mg/mLintravenousBRACCO DIAGNOSTICS INC2004-11-23Not applicableUs
Multihancesolution529 mgintravenousBracco Imaging Canada2004-10-28Not applicableCanada
Multihanceinjection, solution529 mg/mLintravenousBRACCO DIAGNOSTICS INC2004-11-23Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
Multihance MultipackBracco
Brand mixturesNot Available
Gadobenate dimeglumine
  • Monoisotopic Mass: 1058.317829604
  • Average Mass: 1058.15
CAS number113662-23-0
WeightAverage: 667.73
Monoisotopic: 668.09649
Chemical FormulaC22H28GdN3O11
gadolinium(3+) ion 4-carboxy-8,11-bis(carboxylatomethyl)-5-(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oate
DescriptionThis compound belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassPentacarboxylic acids and derivatives
Direct ParentPentacarboxylic acids and derivatives
Alternative Parents
  • Pentacarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Benzylether
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic zwitterion
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic salt
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
IndicationGadobenate 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.
PharmacodynamicsGadobenate 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 actionBased 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).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingPlasma protein binding is low, weak, and transient.

Not metabolized.

Route of eliminationGadobenate ion is eliminated predominately via the kidneys, with 78% to 96% of an administered dose recovered in the urine.
Half life1 hour
  • 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]
ToxicityGadolinium-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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption-0.9749
Blood Brain Barrier-0.9391
Caco-2 permeable-0.691
P-glycoprotein substrateSubstrate0.8261
P-glycoprotein inhibitor INon-inhibitor0.7702
P-glycoprotein inhibitor IINon-inhibitor0.7288
Renal organic cation transporterNon-inhibitor0.8635
CYP450 2C9 substrateNon-substrate0.8598
CYP450 2D6 substrateNon-substrate0.8006
CYP450 3A4 substrateNon-substrate0.6356
CYP450 1A2 substrateNon-inhibitor0.8637
CYP450 2C9 inhibitorNon-inhibitor0.8597
CYP450 2D6 inhibitorNon-inhibitor0.8675
CYP450 2C19 inhibitorNon-inhibitor0.8851
CYP450 3A4 inhibitorNon-inhibitor0.9349
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9905
Ames testNon AMES toxic0.8062
BiodegradationNot ready biodegradable0.8088
Rat acute toxicity2.3557 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8499
hERG inhibition (predictor II)Non-inhibitor0.6371
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
  • Bracco diagnostics inc
Dosage forms
Injection, solutionintravenous529 mg/mL
Solutionintravenous529 mg
Unit descriptionCostUnit
Multihance 529 mg/ml vial6.87USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4916246 No1995-04-102012-04-10Us
Experimental PropertiesNot Available
Predicted Properties
Water Solubility0.768 mg/mLALOGPS
pKa (Strongest Acidic)0.085ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area213.94 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity154.36 m3·mol-1ChemAxon
Polarizability48.32 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
SpectraNot Available
Synthesis Reference

Pier Lucio Anelli, Pierfrancesco Morisini, Silvia Ceragioli, Fulvio Uggeri, Luciano Lattuada, Roberta Fretta, Aurelia Ferrigato, “Process for the Preparation of Gadobenate Dimeglumine Complex in a Solid Form.” U.S. Patent US20120232151, issued September 13, 2012.

General References
  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:10608412 ]
  2. Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. [PubMed:17921081 ]
  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:1546612 ]
  4. Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. [PubMed:9818314 ]
  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:10608397 ]
  6. Sweetman, Sean C. (2009). Contrast Media. In Martindale : The Complete Drug Reference, 36th Edition 2 Volume Set (36th ed., pp. 1478). Pharmaceutical Press. [ISBN:978-0-85369-840-1 ]
External Links
ATC CodesV08CA08
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (247 KB)
MSDSNot Available
Drug Interactions
CitalopramGadobenate Dimeglumine may increase the QTc-prolonging activities of Citalopram.
DofetilideGadobenate Dimeglumine may increase the QTc-prolonging activities of Dofetilide.
GoserelinGoserelin may increase the QTc-prolonging activities of Gadobenate Dimeglumine.
IvabradineIvabradine may increase the QTc-prolonging activities of Gadobenate Dimeglumine.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Gadobenate Dimeglumine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Gadobenate Dimeglumine.
OctreotideOctreotide may increase the QTc-prolonging activities of Gadobenate Dimeglumine.
Food InteractionsNot Available


Pharmacological action
General Function:
Toxic substance binding
Specific Function:
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. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
Uniprot ID:
Molecular Weight:
69365.94 Da
  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:16118549 ]
  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:9055236 ]
  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:9406019 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23