Identification

Summary

Gadoversetamide is a gadolinium compound used as a contrast agent in MRI tests of the brain, spine, and liver.

Generic Name
Gadoversetamide
DrugBank Accession Number
DB00538
Background

Gadoversetamide, marketed under the trade name OptiMARK, is a gadolinium compound used as a contrast agent in magnetic resonance imaging (MRI), particularly imaging of the brain, spine and liver.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 661.76
Monoisotopic: 662.154667866
Chemical Formula
C20H34GdN5O10
Synonyms
  • Gadoversetamid
  • Gadoversetamida
  • Gadoversetamide
  • Gadoversetamidum
External IDs
  • MP 1177
  • MP-1177

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.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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]
Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Active Moieties
NameKindUNIICASInChI Key
Gadolinium cation (3+)ionicAZV954TZ9N22541-19-1RJOJUSXNYCILHH-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OptimarkSolution330.9 mg / mLIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada flag
OptimarkSolution330.9 mg / mLIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada flag
OptimarkInjection, solution500 micromol/mlIntravenousMallinckrodt Deutschland Gmb H2016-09-202017-12-11EU flag
OptimarkInjection, solution500 micromol/mlIntravenousMallinckrodt Deutschland Gmb H2016-09-202017-12-11EU flag
OptimarkInjection, solution500 micromol/mlIntravenousMallinckrodt Deutschland Gmb H2016-09-202017-12-11EU flag
OptimarkInjection, solution500 micromol/mlIntravenousMallinckrodt Deutschland Gmb H2016-09-202017-12-11EU flag
OptimarkSolution330.9 mg / mLIntravenousLiebel Flarsheim Company Llc2001-08-202018-03-23Canada flag
OptimarkSolution330.9 mg / mLIntravenousLiebel Flarsheim Company LlcNot applicableNot applicableCanada flag
OptimarkInjection, solution500 micromol/mlIntravenousMallinckrodt Deutschland Gmb H2016-09-202017-12-11EU flag
OptimarkInjection, solution500 micromol/mlIntravenousMallinckrodt Deutschland Gmb H2016-09-202017-12-11EU flag

Categories

ATC Codes
V08CA06 — Gadoversetamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alpha-amino acid / Alpha-amino acid amide / Amine / Amino acid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid salt / Dialkyl ether
show 14 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
gadolinium coordination entity (CHEBI:31644)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
RLM74T3Z9D
CAS number
131069-91-5
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+) 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

References

General References
Not Available
Human Metabolome Database
HMDB0014678
KEGG Drug
D01646
PubChem Compound
444013
PubChem Substance
46504481
ChemSpider
392041
RxNav
228833
ChEBI
31644
ChEMBL
CHEMBL1200457
PharmGKB
PA164743703
Wikipedia
Gadoversetamide
FDA label
Download (925 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticPathological Processes1
2CompletedDiagnosticBrain Diseases / Spinal Cord Diseases1
Not AvailableCompletedBasic ScienceCoronary Artery Disease (CAD)1

Pharmacoeconomics

Manufacturers
  • Mallinckrodt inc
Packagers
  • Mallinckrodt Inc.
Dosage Forms
FormRouteStrength
InjectionIntravenous100 mg
Injection, solutionIntravenous
Injection, solutionIntravenous0.5 mmol/1mL
Injection, solutionIntravenous500 micromol/ml
SolutionIntravenous330.9 mg / mL
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)Region
US5130120No1992-07-142009-07-14US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.98 mg/mLALOGPS
logP0.36ALOGPS
logP-8.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.91ChemAxon
pKa (Strongest Basic)8.34ChemAxon
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

Drug created at June 13, 2005 13:24 / Updated at May 21, 2022 00:27