gadolinium(3+) ion 2-[bis({2-[(carboxylatomethyl)({[(2-methoxyethyl)carbamoyl]methyl})amino]ethyl})amino]acetate

• ChemBase ID: 420
• Molecular Formular: C20H34GdN5O10
• Molecular Mass: 661.76146
• Monoisotopic Mass: 662.15467031
• SMILES: [Gd+3].[O-]C(=O)CN(CCN(CC(=O)NCCOC)CC(=O)[O-])CCN(CC(=O)NCCOC)CC(=O)[O-]
• Canonical SMILES: COCCNC(=O)CN(CC(=O)[O-])CCN(CC(=O)[O-])CCN(CC(=O)NCCOC)CC(=O)[O-].[Gd+3]
• InChI: InChI=1S/C20H37N5O10.Gd/c1-34-9-3-21-16(26)11-24(14-19(30)31)7-5-23(13-18(28)29)6-8-25(15-20(32)33)12-17(27)22-4-10-35-2;/h3-15H2,1-2H3,(H,21,26)(H,22,27)(H,28,29)(H,30,31)(H,32,33);/q;+3/p-3
• InChIKey: HBEAOBRDTOXWRZ-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: gadolinium(3+) ion 2-[bis({2-[(carboxylatomethyl)({[(2-methoxyethyl)carbamoyl]methyl})amino]ethyl})amino]acetate
• IUPAC Traditional name: gadolinium(3+) 2-[bis({2-[(carboxylatomethyl)({[(2-methoxyethyl)carbamoyl]methyl})amino]ethyl})amino]acetate
• Brand Name: OptiMARK
• Synonyms: Gadoversetamide [USAN:INN:BAN]; gadoversetamide; Gadoversetamide

Database IDs

• CAS Number: 131069-91-5
• PubChem SID: 160963883; 46504481
• PubChem CID: 444013

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.322693
• H Acceptors: 13
• H Donor: 2
• LogD (pH = 5.5): -9.52119
• LogD (pH = 7.4): -12.7595005
• Log P: -7.0427794
• Molar Refractivity: 154.4854 cm^3
• Polarizability: 47.47008 Å^3
• Polar Surface Area: 206.77 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.36
• LOG S: -2.41
• Solubility (Water): 2.98e+00 g/l

DETAILS

DrugBank - DB00538

• Drug Groups: approved; investigational
• Description: Gadoversetamide is a gadolinium compound used as a contrast agent in magnetic resonance imaging (MRI), particularly imaging of the brain, spine and liver. It is marketed under the trade name OptiMARK.
• Indication: Gadoversetamide is an MRI contrast agent used for MRI diagnostic procedures to provide increased enhancement and visualization of lesions of the brain, spine and liver, including tumors.
• Affected Organisms: Humans and other mammals
• Biotransformation: None detected
• Half Life: Distribution 13.3 ± 6.8 (mean) minutes, elimination 103.6 ± 19.5 (mean) minutes.
• Elimination: The mean cumulative urinary excretion of gadoversetamide at 72 hours was approximately 93.5% for renal impaired patients and 95.8% for subjects with normal renal function
• Distribution: * 162 ± 25 mL/kg [normal subjects]
• Clearance: * 72 +/- 16.3 mL/hr/kg [healthy]
• External Links: Wikipedia