Gadobenate dimeglumineProduct ingredient for Gadobenic acid

Name
Gadobenate dimeglumine
Drug Entry
Gadobenic acid

Gadobenic acid (in the form of gadobenate dimeglumine) is an MRI contrast agent used primarily for MR imaging of the liver. It can also be used for visualizing the CNS and heart. In contrast to conventional extracellular fluid contrast agents, gadobenate dimeglumine is characterized by a weak and transient binding capacity to serum proteins. This binding leads to an increased relaxivity of gadobenate dimeglumine and, consequently, to a considerably increased signal intensity over that of other agents.

Accession Number
DBSALT001794
Structure
Thumb
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+) ion 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
PropertyValueSource
logP-4.1ChemAxon
pKa (Strongest Acidic)0.085ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area213.94 Å2ChemAxon
Rotatable Bond Count32ChemAxon
Refractivity154.36 m3·mol-1ChemAxon
Polarizability48.51 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon