Gadobenate dimeglumineProduct ingredient for Gadobenic acid
- Name
- Gadobenate dimeglumine
- Drug Entry
- Gadobenic acid
Gadobenic acid, usually available in the salt form gadobenate dimeglumine, is a linear MRI gadolinium-based contrast agent (GBCA) used primarily for MR imaging of the liver.9 It differs from other GBCAs due to the benzene ring that confers weak protein binding, thus leading to an increased R1 and R2 relaxivity.8 As gadobenate dimeglumine is specifically taken up by hepatocytes and excreted through the biliary system, it is a useful contrast agent for liver MRI.3
Gadobenate dimeglumine was approved by the FDA in November 2004 under the brand name MultiHance.8
- Accession Number
- DBSALT001794
- Structure
Structure for Gadobenate dimeglumine (DBSALT001794)
- Synonyms
- Gadobenic acid meglumine / Gadobenoate dimeglumine / Meglumine gadobenate
- UNII
- 3Q6PPC19PO
- CAS Number
- 127000-20-8
- Weight
- Average: 1058.15
Monoisotopic: 1058.317829604 - Chemical Formula
- C36H62GdN5O21
- InChI Key
- OCDAWJYGVOLXGZ-VPVMAENOSA-K
- InChI
- InChI=1S/C22H31N3O11.2C7H17NO5.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;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1
- IUPAC Name
- gadolinium(3+) bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate
- SMILES
- [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CCN(CCN(CC(O)=O)C(COCC1=CC=CC=C1)C([O-])=O)CC([O-])=O)CC([O-])=O
- External Links
- Human Metabolome Database
- HMDB0014881
- ChemSpider
- 170831
- PharmGKB
- PA164745426
- Wikipedia
- Gadobenic_acid
- Predicted Properties
Property Value Source Water Solubility 0.705 mg/mL ALOGPS logP 1.06 ALOGPS logP -4.3 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 2.02 Chemaxon pKa (Strongest Basic) 8.83 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 213.94 Å2 Chemaxon Rotatable Bond Count 32 Chemaxon Refractivity 154.36 m3·mol-1 Chemaxon Polarizability 48.51 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon