CAS 131069-91-5|gadolinium(3+) ion 2-[bis({2-[(carboxylatomethyl)({[(2-methoxyethyl)carbamoyl]methyl})amino]ethyl})amino]acetate|Gadoversetamide|Gadoversetamide [USAN:INN:BAN]|gadolinium(3+) 2-[bis(...

General Information

Structure

Molecular Formula

C₂₀H₃₄GdN₅O₁₀

Molecular Mass

661.76146

Exact Mass

662.15467031

Charge

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

Canonic Smiles

COCCNC(=O)CN(CC(=O)[O-])CCN(CC(=O)[O-])CCN(CC(=O)NCCOC)CC(=O)[O-].[Gd+3]

Isomeric Smiles

[Gd+3].[O-]C(=O)CN(CCN(CC(=O)NCCOC)CC(=O)[O-])CCN(CC(=O)NCCOC)CC(=O)[O-]

Calculated Properties

JChem

LogD (pH = 7.4)

-13.13

LogD (pH = 5.5)

-9.30

Log P

-6.35

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

2.18

Polar Surface Area

206.77

Polarizability

49.57

Molar Refractivity

154.49

LOG S

0.72

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

GadoversetamideGadoversetamide [USAN:INN:BAN]gadoversetamidegadoversetamidegadoversetamide

IUPAC name

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

Brand Name

OptiMARK

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

PubChem CID

444013

CAS Number

131069-91-5

PubChem SID

46504481160963883135610207

SureChEMBL Database

SCHEMBL237265

Wikipedia Title

Gadoversetamide

Reaxys Registry

11736544

MetaboLights Database

CompTox Database

CHEBI ID

DrugBank ID

KEGG DRUG Database

Gmelin ID

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

ChEBI

CHEBI:31644

A gadolinium coordination entity that consists of Gd(3+) coordinated to 3,6,9-triazaundecadiamide in which each of the amide nitrogens is substituted by a 2-methoxyethyl group and in which the nitrogens at positions 3, 6, and 9 are each substituted by carboxylatomethyl group. The gadolinium is coordinated to the three tertiary amino groups as well as to the carboxylate groups. A white odourless powder that is freely soluble in water, gadoversetamide has paramagnetic properties and is used as a contrast agent in magnetic resonance imaging. It distributes mainly in extracellular fluid, but does not cross the blood-brain barrier. It is used particularly in imaging the brain, spine and liver.

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity

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