Gadobenic acid

Gadobenic acid (INN, brand 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.[3]

Gadobenic acid
Clinical data
Trade namesMultihance
Other namesgadobenate dimeglumine (USAN US)
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ATC code
Legal status
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Identifiers
IUPAC name
  • dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).
CAS Number
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Chemical and physical data
FormulaC22H28GdN3O11
Molar mass667.73 g·mol−1
3D model (JSmol)
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 N
  • Key:MXZROTBGJUUXID-UHFFFAOYSA-K N
 NY (what is this?)  (verify)

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.[4] 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.[4]

References
  1. "Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC)". (emc). 14 August 2019. Retrieved 29 August 2021.
  2. "Multihance- gadobenate dimeglumine injection, solution". DailyMed. Retrieved 29 August 2021.
  3. 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.
  4. Uggeri F, Aime S, Anelli PL, Botta M, Brocchetta M, de Haeen 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". Inorganic Chemistry. 34 (3): 633–643. doi:10.1021/ic00107a017. ISSN 0020-1669.


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