Gadobenic acid

Gadobenic acid

Systematic (IUPAC) name
dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).
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
Molar mass	667.72 g/mol
SMILES [H+].[H+].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)C(C([O-])=O)COCc1ccccc1
InChI InChI=1S/C22H31N3O11.Gd/c26-18(27)10-23(6-7-24(11-19(28)29)12-20(30)31)8-9-25(13-21(32)33)17(22(34)35)15-36-14-16-4-2-1-3-5-16;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);/q;+3/p-3 Key:MXZROTBGJUUXID-UHFFFAOYSA-K
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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

1. Sweetman, Sean C., ed. (2009). "Contrast Media". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 1478. ISBN 978-0-85369-840-1.
2. 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.