Jump to content

Gadobenic acid

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Tricker108 (talk | contribs) at 21:39, 20 June 2016 (Updated the empirical formula and molecular weight (molar mass) of the compound from pubchem / fda). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Gadobenic acid
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC36H62GdN5O21 [1] [2]
Molar massExpression error: Unexpected < operator1058.14838 g/mol [3] [4]Expression error: Unexpected < operator
3D model (JSmol)
  • [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=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
 ☒NcheckY (what is this?)  (verify)

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.[5]

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. [6] 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.[6]

References

  1. ^ https://pubchem.ncbi.nlm.nih.gov/compound/6918204#section=Top
  2. ^ https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021358s008lbl.pdf
  3. ^ https://pubchem.ncbi.nlm.nih.gov/compound/6918204#section=Top
  4. ^ https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021358s008lbl.pdf
  5. ^ 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.
  6. ^ a b 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)