Gadobenate Dimeglumine

Title: Gadobenate Dimeglumine
CAS Registry Number: 127000-20-8
CAS Name: 1-Deoxy-1-(methylamino)-D-glucitol [4-(carboxy-kO)-5,8,11-tris[(carboxy-kO)methyl]-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5-)-kN5,kN8,kN11,kO13]gadolinate(2-) (2:1)
Additional Names: gadolinium benzyloxypropionictetraacetate dimeglumine; Gd-BOPTA/Dimeg
Manufacturers' Codes: B-19036/7
Trademarks: MultiHance (Bracco)
Molecular Formula: C36H62GdN5O21
Molecular Weight: 1058.15
Percent Composition: C 40.86%, H 5.91%, Gd 14.86%, N 6.62%, O 31.75%
Literature References: Intravascular paramagnetic MRI contrast agent. Prepn: E. Felder et al., EP 230893; eidem, US 4916246 (1987, 1990 both to Bracco); F. Ungerri et al., Inorg. Chem. 34, 633 (1995). HPLC determn in biological samples: T. Arbughi et al., J. Chromatogr. B 713, 415 (1998). Physicochemical properties: C. de Haen et al., J. Comput. Assist. Tomogr. 23, Suppl. 1, S161 (1999). Pharmacology: P. Tirone et al., ibid. S195. Pharmacokinetics: V. Lorusso et al., ibid. S181. Toxicology: A. Morisetti et al., ibid. S207. Clinical study in MRI of liver lesions: J. Petersein et al. Radiology 215, 727 (2000). Review of clinical studies: B. Hamm et al., J. Comput. Assist. Tomogr. 23, Suppl. 1, S53-S60 (1999).
Properties: Hygroscopic powder. mp 124°. Freely sol in water, sol in methanol. Practically insol in n-butanol, n-octanol, chloroform. Abs max 257.8 nm (e 203). [a]36520 -26.9° (c = 1.45 in water). Prepd as 0.5M soln, osmolality (37°) 1.97 mol/kg. d20 1.22. Viscosity (mPa.s): 9.2 (20°), 5.3 (37°). LD50 i.v. in mice (mmol/kg): 5.7 (at 1 mL/min), 7.9 (at 0.2 mL/min); LD50 i.v. in rats (mmol/kg): 6.6 (at 6 mL/min), 9.2 (at 1 mL/min) (Morisetti).
Melting point: mp 124°
Optical Rotation: [a]36520 -26.9° (c = 1.45 in water)
Absorption maximum: Abs max 257.8 nm (e 203)
Density: d20 1.22
Toxicity data: LD50 i.v. in mice (mmol/kg): 5.7 (at 1 mL/min), 7.9 (at 0.2 mL/min); LD50 i.v. in rats (mmol/kg): 6.6 (at 6 mL/min), 9.2 (at 1 mL/min) (Morisetti)
Therap-Cat: Diagnostic aid (MRI contrast agent).
Keywords: Diagnostic Aid (MRI Contrast Agent).
Gadodiamide Gadofosveset Gadopentetic Acid Gadoteridol Gadoversetamide

Gadobenic acid
Structure of Gadobenic acid.png
Systematic (IUPAC) name
2-[2-[2-[bis(2-oxido-2-oxoethyl)amino]ethyl-(2-oxido-2-oxoethyl)amino]ethyl-
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 113662-23-0 N
ATC code V08CA08
PubChem CID 105124
DrugBank DB00996
ChemSpider 94843 N
UNII 15G12L5X8K YesY
KEGG D08018 YesY
ChEMBL CHEMBL1200571 N
Chemical data
Formula C22H28GdN3O11 
Mol. mass 667.72 g/mol
 N (what is this?)  (verify)

Gadobenic acid (tradename MultiHance) is a complex of gadolinium with the ligand BOPTA. In the form of the diglumine salt it functions as a gadolinium-based MRI contrast medium, under the trade name gadobenate dimeglumine.

BOPTA is a derivative of DTPA in which one terminal carboxyl group, –C(O)OH is replaced by -C–O–CH2C6H5. Thus gadobenic acid is closely related to gadopentetic acid. BOPTA itself was first synthesized in 1995. [1] In the "gadobenate" ion gadolinium ion is 9-coordinate with BOPTA acting as a 8-coordinating ligand. The ninth position is occupied by a water molecule, which exchanges rapidly with water molecules in the immediate vicinity of the strongly paramagnetic complex, providing a mechanism for MRI contrast enhancement. 139La NMR studies on the diamagnetic La-BOPTA2- complex suggest that the Gd complex maintains in solution the same kind of coordination as found, by X-ray crystallography, in the solid state for Gd-BOPTA disodium salt.[1]

  1. ^ a b Uggeri, F.; Aime, S., Anelli, P.L., Botta, M., Brocchetta, M., De Haën, C., Ermondi, G., Grandi, M., Paoli, P. (1995). "Novel contrast agents for magnetic resonance imaging. Synthesis and characterization of the ligand BOPTA and its Ln(III) complexes (Ln = Gd, La, Lu). X-ray structure of disodium (TPS-9-145337286-C-S)-[4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8, 11-triazatridecan-13-oato(5-)]gadolinate(2-) in a mixture with its enantiomer". Inorg. Chem. 34 (3): 633–642. doi:10.1021/ic00107a017.