Gadobenate Dimeglumine

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Product Details:

  • CAS No: 127000-20-8
  • AHFC code: 32:00.0
  • Synonyms: B 1903617, B19036/7, Dihydrogen ((+-)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5-))gadolinate(2-), compound with 1-deoxy-1-(methylamino)-D-glucitol (1:2), Gadobenate Dimeglumine, Gadobenate Meglumine, Gadobenic acid dimeglumine salt, Gadolinate(2-), (4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5-)-N(sup 5),N(sup 8),N(sup 11),O(sup 4),O(sup 5),O(sup 8),O(sup 11),O(sup 13))-, dihydrogen, comp. with 1-deoxy-1-(methylamino)-D-glucitol (1:2), Gd-Bopta/dimeg, HSDB 7546, Multihance, Multihance multipack, UNII-3Q6PPC19PO
  • ATC Code: V08CA08
  • Chemical Formula: C22-H28-Gd-N3-O11.2C7-H17-N-O5
  • Molecular Weight: 1061.1735
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00743
  • SMILES: [H+].[H+].CNC[C,,H]([C,H]([C,,H]([C,,H](CO)O)O)O)O.CNC[C,,H]([C,H]([C,,H]([C,,H](CO)O)O)O)O.c1ccc(cc1)COCC2C(=O)[O-][Gd+3]345678N2(CCN3(CCN4(CC(=O)[O-]5)CC(=O)[O-]6)CC(=O)[O-]7)CC(=O)[O-]8
  • InChl:
  • PubChem:
  • IUPAC: 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

Additional Details

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.
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.
Mode 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).
Not metabolized.
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.
General Reference:
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. PubmedMorana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. PubmedVogl 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. PubmedKirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. PubmedClement 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
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