Gadobenic acid is a gadolinium compound used as a contrast agent in MRIs.
- Brand Names
- Generic Name
- Gadobenic acid
- DrugBank Accession Number
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.
- Small Molecule
- Approved, Investigational
- Average: 667.73
- Chemical Formula
- Acide gadobenique
- Acido gadobenico
- Acidum gadobenicum
- Gadobenic acid
- External IDs
- B 19036
- B 19036/7
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.Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.
- Associated Conditions
- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
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).
- Volume of distribution
- Protein binding
Plasma protein binding is low, weak, and transient.
- Route of elimination
Gadobenate ion is eliminated predominately via the kidneys, with 78% to 96% of an administered dose recovered in the urine.
- 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]
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
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.
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Abacavir Gadobenic acid may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Gadobenic acid which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Gadobenic acid which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Gadobenic acid which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Gadobenic acid which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Gadobenic acid which could result in a higher serum level. Aclidinium Gadobenic acid may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Gadobenic acid. Acyclovir Acyclovir may decrease the excretion rate of Gadobenic acid which could result in a higher serum level. Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Gadobenic acid which could result in a higher serum level.Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more
- Food Interactions
- No interactions found.
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Gadobenate dimeglumine 3Q6PPC19PO 127000-20-8 OCDAWJYGVOLXGZ-VPVMAENOSA-K
- Active Moieties
Name Kind UNII CAS InChI Key Gadolinium cation (3+) ionic AZV954TZ9N 22541-19-1 RJOJUSXNYCILHH-UHFFFAOYSA-N
- International/Other Brands
- Multihance Multipack (Bracco)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image MultiHance Injection, solution 529 mg/1mL Intravenous Bracco Diagnostics Inc 2004-11-23 Not applicable MultiHance Solution 529 mg / mL Intravenous Bracco Imaging S.P.A. 2004-10-28 Not applicable MultiHance Injection, solution 529 mg/1mL Intravenous Bracco Diagnostics Inc 2004-11-23 Not applicable
- ATC Codes
- V08CA08 — Gadobenic acid
- Drug Categories
- Amino Sugars
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Gadolinium-based Contrast Agent
- Magnetic Resonance Contrast Activity
- Magnetic Resonance Imaging Contrast Media
- Moderate Risk QTc-Prolonging Agents
- Other Diagnostics
- Paramagnetic Contrast Agent
- Paramagnetic Contrast Media
- QTc Prolonging Agents
- Sugar Alcohols
- Not classified
- Affected organisms
- Humans and other mammals
- CAS number
- InChI Key
- IUPAC Name
- gadolinium(3+) ion 4-carboxy-8,11-bis(carboxylatomethyl)-5-(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oate
- 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.US20120232151
- General References
- 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. [Article]
- Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. [Article]
- 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. [Article]
- Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. [Article]
- 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. [Article]
- 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]
- FDA label
- Download (247 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Brain Pathology 1 4 Completed Diagnostic Brain Diseases 1 4 Completed Diagnostic Brain Lesions 1 4 Completed Diagnostic Neoplasms, Brain 1 4 Recruiting Diagnostic Colorectal Carcinoma (CRC) / Hepatic Metastases / Oligometastatic Disease 1 4 Recruiting Other Cognitive Functioning / Contrast Medium / Motor Function 1 3 Completed Diagnostic Breast Cancer 1 3 Completed Diagnostic Carotid, Aortic, Renal or Peripheral Artery Disease 1 3 Completed Diagnostic Peripheral Vascular Disease Patient 1 3 Completed Diagnostic Steno-Occlusive Disease 1
- Bracco diagnostics inc
- Bracco Diagnostics Inc.
- Nycomed Inc.
- Patheon Inc.
- Dosage Forms
Form Route Strength Injection Intravenous Injection, solution Intravenous Injection, solution Intravenous 529 mg/1mL Solution Intravenous 334 mg/1ml Solution Intravenous 529 mg / mL Injection, solution Parenteral Solution Intravenous
Unit description Cost Unit Multihance 529 mg/ml vial 6.87USD mlDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent Number Pediatric Extension Approved Expires (estimated) Region US4916246 No 1990-04-10 2012-04-10
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.768 mg/mL ALOGPS logP 0.92 ALOGPS logP -4.1 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 0.085 ChemAxon pKa (Strongest Basic) 9.58 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 213.94 Å2 ChemAxon Rotatable Bond Count 20 ChemAxon Refractivity 154.36 m3·mol-1 ChemAxon Polarizability 48.32 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9749 Blood Brain Barrier - 0.9391 Caco-2 permeable - 0.691 P-glycoprotein substrate Substrate 0.8261 P-glycoprotein inhibitor I Non-inhibitor 0.7702 P-glycoprotein inhibitor II Non-inhibitor 0.7288 Renal organic cation transporter Non-inhibitor 0.8635 CYP450 2C9 substrate Non-substrate 0.8598 CYP450 2D6 substrate Non-substrate 0.8006 CYP450 3A4 substrate Non-substrate 0.6356 CYP450 1A2 substrate Non-inhibitor 0.8637 CYP450 2C9 inhibitor Non-inhibitor 0.8597 CYP450 2D6 inhibitor Non-inhibitor 0.8675 CYP450 2C19 inhibitor Non-inhibitor 0.8851 CYP450 3A4 inhibitor Non-inhibitor 0.9349 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9905 Ames test Non AMES toxic 0.8062 Carcinogenicity Non-carcinogens 0.9179 Biodegradation Not ready biodegradable 0.8088 Rat acute toxicity 2.3557 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8499 hERG inhibition (predictor II) Non-inhibitor 0.6371
- Mass Spec (NIST)
- Not Available
- Not 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 colloid...
- Gene Name
- Uniprot ID
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created on June 13, 2005 13:24 / Updated on September 19, 2021 19:53