Gadoterate meglumineProduct ingredient for Gadoteric acid
- Name
- Gadoterate meglumine
- Drug Entry
- Gadoteric acid
Gadoteric acid, commonly used in the salt form gadoterate meglumine, is a macrocyclic, ionic gadolinium-based contrast agent (GBCA).1 It is composed of the organic acid DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) used for its chelating properties, and gadolinium (Gd3+).2 Gadoterate meglumine has one of the highest thermodynamic stability, apparent stability, and kinetic stability, partly due to its macrocyclic structure, and thus has a more favorable safety profile due to a decreased tendency of gadolinium dechelation.3,4
Gadoterate is approved by the FDA under the brand name DOTAREM on 20th March 2013 for intravenous uses with magnetic resonance imaging (MRI) in the brain (intracranial), spine, and associated tissues in adult and pediatric patients (2 years of age and older) to detect and visualize areas with disruption of the blood-brain barrier (BBB) and/or abnormal vascularity.7
- Accession Number
- DBSALT001229
- Structure
Structure for Gadoterate meglumine (DBSALT001229)
- Synonyms
- Not Available
- UNII
- L0ND3981AG
- CAS Number
- 92943-93-6
- Weight
- Average: 753.86
Monoisotopic: 754.20202 - Chemical Formula
- C23H42GdN5O13
- InChI Key
- RYHQMKVRYNEBNJ-BMWGJIJESA-K
- InChI
- InChI=1S/C16H28N4O8.C7H17NO5.Gd/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26;1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28);4-13H,2-3H2,1H3;/q;;+3/p-3/t;4-,5+,6+,7+;/m.0./s1
- IUPAC Name
- gadolinium(3+) ion (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol 2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetate
- SMILES
- [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1
- External Links
- Predicted Properties
Property Value Source Water Solubility 12.8 mg/mL ALOGPS logP 0.23 ALOGPS logP -7.6 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.17 Chemaxon pKa (Strongest Basic) 9.28 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 170.65 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 128.93 m3·mol-1 Chemaxon Polarizability 37.84 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