Gadobenic acid

Gadobenic acid
Clinical data
Trade names	Multihance
Other names	gadobenate dimeglumine (USAN US)
AHFS/Drugs.com	Professional Drug Facts
ATC code	V08CA08 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
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	113662-23-0 ;
PubChem CID	105124;
DrugBank	DB00743 ;
ChemSpider	94843 ;
UNII	15G12L5X8K;
KEGG	D08018 ;
ChEMBL	ChEMBL1200571 ;
CompTox Dashboard (EPA)	DTXSID00921145 ;
Chemical and physical data
Formula	C22H28GdN3O11
Molar mass	667.73 g·mol−1
3D model (JSmol)	Interactive image;
	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, 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.^[4]

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.^[5] 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.^[5]

References

^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
^ "Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC)". (emc). 14 August 2019. Retrieved 29 August 2021.
^ "Multihance- gadobenate dimeglumine injection, solution". DailyMed. Retrieved 29 August 2021.
^ 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.
^ ^a ^b 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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[1] "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.

[2] "Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC)". (emc). 14 August 2019. Retrieved 29 August 2021.

[3] "Multihance- gadobenate dimeglumine injection, solution". DailyMed. Retrieved 29 August 2021.

[Martindale-4] 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.

[UggeriAime1995-5] 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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