Gadobenic acid
Systematic (IUPAC) name | |
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dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).
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Clinical data | |
AHFS/Drugs.com | International Drug Names |
Identifiers | |
CAS Number | 113662-23-0 |
ATC code | V08CA08 (WHO) |
PubChem | CID: 105124 |
DrugBank | DB00743 |
ChemSpider | 94843 |
UNII | 15G12L5X8K |
KEGG | D08018 |
ChEMBL | CHEMBL1200571 |
Chemical data | |
Formula | C22H28GdN3O11 |
Molecular mass | 667.72 g/mol |
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Gadobenic acid (INN, trade name MultiHance) is a complex of gadolinium with the ligand BOPTA. In the form of the methylglucamine salt meglumine gadobenate (INNm) or gadobenate dimeglumine (USAN), it is used as a gadolinium-based MRI contrast medium.[1]
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. [2] In the "gadobenate" ion gadolinium ion is 9-coordinate with BOPTA acting as an 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.[2]
References
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