Chemistry:Gadobenic acid
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| Trade names | Multihance |
| Other names | gadobenate dimeglumine (USAN US) |
| AHFS/Drugs.com | Professional Drug Facts |
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| Formula | C22H28GdN3O11 |
| Molar mass | 667.73 g·mol−1 |
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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.[3]
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
- ↑ "Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC)". 14 August 2019. https://www.medicines.org.uk/emc/product/1388/smpc.
- ↑ "Multihance- gadobenate dimeglumine injection, solution". https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=59077a3e-5f03-4342-ae24-856267545631.
- ↑ Sweetman, Sean C., ed (2009). "Contrast Media". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. pp. 1478. ISBN 978-0-85369-840-1.
- ↑ 4.0 4.1 "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. 1995. doi:10.1021/ic00107a017. ISSN 0020-1669.
External links
- "Gadobenic acid". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/rn/113662-23-0.
- "Gadobenate Dimeglumine". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/gadobenate%20dimeglumine.
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