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Identification
NameGadoversetamide
Accession NumberDB00538  (APRD00993)
TypeSmall Molecule
GroupsApproved, 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
OptiMARK
External Identifiers
  • MP 1177
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Optimarkinjection, solution.5 mmol/mLintravenousMallinckrodt Inc.2010-12-10Not applicableUs
Optimarksolution330.9 mgintravenousLiebel Flarsheim Canada IncNot applicableNot applicableCanada
Optimarksolution330.9 mgintravenousLiebel Flarsheim Canada IncNot applicableNot applicableCanada
Optimarksolution330.9 mgintravenousLiebel Flarsheim Canada IncNot applicableNot applicableCanada
Optimarksolution330.9 mgintravenousLiebel Flarsheim Canada IncNot applicableNot applicableCanada
Optimarksolution330.9 mgintravenousLiebel Flarsheim Canada Inc2001-08-20Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIRLM74T3Z9D
CAS number131069-91-5
WeightAverage: 661.76
Monoisotopic: 662.154667866
Chemical FormulaC20H34GdN5O10
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid salt
  • Carboxamide group
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationGadoversetamide 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.
PharmacodynamicsNot Available
Mechanism of actionBased 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.
Related Articles
AbsorptionNot Available
Volume of distribution
  • 162 ± 25 mL/kg [normal subjects]
Protein bindingNot Available
Metabolism

None detected

Route of eliminationThe 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 lifeDistribution 13.3 ± 6.8 (mean) minutes, elimination 103.6 ± 19.5 (mean) minutes.
Clearance
  • 72 +/- 16.3 mL/hr/kg [healthy]
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Mallinckrodt inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous.5 mmol/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)
US5130120 No1992-07-142009-07-14Us
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesV08CA06
AHFS Codes
  • 36:68.00
PDB EntriesNot Available
FDA labelDownload (925 KB)
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on February 19, 2014 10:27