Gadoversetamide

Identification

Name
Gadoversetamide
Accession Number
DB00538  (APRD00993)
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • Gadoversetamid
  • Gadoversetamida
  • Gadoversetamide
  • Gadoversetamidum
External IDs
MP 1177 / MP-1177
Active Moieties
NameKindUNIICASInChI Key
Gadolinium cation (3+)ionicAZV954TZ9N22541-19-1RJOJUSXNYCILHH-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OptimarkSolution330.9 mgIntravenousLiebel Flarsheim Company Llc2001-08-20Not applicableCanada
OptimarkSolution330.9 mgIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada
OptimarkSolution330.9 mgIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada
OptimarkSolution330.9 mgIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada
OptimarkSolution330.9 mgIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada
OptimarkInjection, solution0.5 mmol/1mLIntravenousLiebel-Flarsheim Company LLC2012-01-222018-09-15Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
OptimarkGadoversetamide (500 micromol/ml)Injection, solutionIntravenousMallinckrodt Deutschland Gmb H2007-07-232017-12-11Eu
Categories
UNII
RLM74T3Z9D
CAS number
131069-91-5
Weight
Average: 661.76
Monoisotopic: 662.154667866
Chemical Formula
C20H34GdN5O10
InChI Key
HBEAOBRDTOXWRZ-UHFFFAOYSA-K
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
IUPAC Name
gadolinium(3+) ion 2-[bis({2-[(carboxylatomethyl)({[(2-methoxyethyl)carbamoyl]methyl})amino]ethyl})amino]acetate
SMILES
[Gd+3].COCCNC(=O)CN(CCN(CCN(CC([O-])=O)CC(=O)NCCOC)CC([O-])=O)CC([O-])=O

Pharmacology

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.

Pharmacodynamics
Not Available
Mechanism of action

Based on the behavior of protons when placed in a strong magnetic field, which is interpreted and transformed into images by magnetic resonance (MR) instruments. MR images are based primarily on proton density and proton relaxation dynamics. MR instruments are sensitive to two different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and T2 (spin-spin or transverse relaxation time). Paramagnetic agents contain one or more unpaired electrons that enhance the T1 and T2 relaxation rates of protons in their molecular environment. In MRI, visualization of normal and pathological brain, spinal and hepatic tissue depends in part on variations in the radio frequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadoversetamide shortens the T1 and T2 relaxation times in tissues where it accumulates. At the recommended dose, the effect is primarily on T1 relaxation time, and produces an increase in signal intensity (brightness). Gadoversetamide does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in CNS lesions that may have a normal blood-brain barrier (e.g., cysts, mature post-operative scars). Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadoversetamide in lesions such as neoplasms, abscesses, and subacute infarcts.

Absorption
Not Available
Volume of distribution
  • 162 ± 25 mL/kg [normal subjects]
Protein binding
Not Available
Metabolism

None detected

Route of 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

Half life

Distribution 13.3 ± 6.8 (mean) minutes, elimination 103.6 ± 19.5 (mean) minutes.

Clearance
  • 72 +/- 16.3 mL/hr/kg [healthy]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014678
KEGG Drug
D01646
PubChem Compound
444013
PubChem Substance
46504481
ChemSpider
392041
ChEBI
31644
ChEMBL
CHEMBL1200457
PharmGKB
PA164743703
Wikipedia
Gadoversetamide
ATC Codes
V08CA06 — Gadoversetamide
AHFS Codes
  • 36:89.00* — Other Diagnostics
FDA label
Download (925 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticPathological Processes1
Not AvailableCompletedBasic ScienceCoronary Artery Disease1

Pharmacoeconomics

Manufacturers
  • Mallinckrodt inc
Packagers
  • Mallinckrodt Inc.
Dosage forms
FormRouteStrength
Injection, solutionIntravenous0.5 mmol/1mL
Injection, solutionIntravenous500 micromol/ml
SolutionIntravenous330.9 mg
Prices
Unit descriptionCostUnit
Optimark 330.9 mg/ml vial4.49USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5130120No1992-07-142009-07-14Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.98 mg/mLALOGPS
logP0.36ALOGPS
logP-7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)2.32ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area206.77 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity154.49 m3·mol-1ChemAxon
Polarizability49.81 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9122
Blood Brain Barrier+0.8868
Caco-2 permeable-0.5196
P-glycoprotein substrateSubstrate0.7041
P-glycoprotein inhibitor INon-inhibitor0.6432
P-glycoprotein inhibitor IINon-inhibitor0.9129
Renal organic cation transporterNon-inhibitor0.8953
CYP450 2C9 substrateNon-substrate0.8552
CYP450 2D6 substrateNon-substrate0.8151
CYP450 3A4 substrateNon-substrate0.5786
CYP450 1A2 substrateNon-inhibitor0.9171
CYP450 2C9 inhibitorNon-inhibitor0.8749
CYP450 2D6 inhibitorNon-inhibitor0.9323
CYP450 2C19 inhibitorNon-inhibitor0.8211
CYP450 3A4 inhibitorNon-inhibitor0.9656
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9637
Ames testNon AMES toxic0.7751
CarcinogenicityNon-carcinogens0.8075
BiodegradationNot ready biodegradable0.5115
Rat acute toxicity2.0763 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9576
hERG inhibition (predictor II)Non-inhibitor0.8903
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Alpha amino acids / Tricarboxylic acids and derivatives / Trialkylamines / Secondary carboxylic acid amides / Carboxylic acid salts / Amino acids / Dialkyl ethers / Carboxylic acids / Organopnictogen compounds / Organic zwitterions
show 4 more
Substituents
Alpha-amino acid amide / Alpha-amino acid / Tricarboxylic acid or derivatives / Carboxamide group / Carboxylic acid salt / Secondary carboxylic acid amide / Tertiary amine / Tertiary aliphatic amine / Amino acid / Ether
show 14 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
gadolinium coordination entity (CHEBI:31644)

Drug created on June 13, 2005 07:24 / Updated on December 10, 2018 06:10