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
Structure for Gadoversetamide (DB00538)
- 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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Liver lesions •••••••••••• ••••• Diagnostic agent Spinal cord lesions •••••••••••• ••••• Diagnostic agent Intracranial lesion •••••••••••• ••••• - Contraindications & Blackbox Warnings
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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
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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 regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Gadolinium cation (3+) ionic AZV954TZ9N 22541-19-1 RJOJUSXNYCILHH-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Optimark Injection, solution 500 micromol/ml Intravenous Mallinckrodt Deutschland Gmb H 2016-09-20 2017-12-11 EU 
Optimark Injection, solution 500 micromol/ml Intravenous Mallinckrodt Deutschland Gmb H 2016-09-20 2017-12-11 EU Optimark Injection, solution 500 micromol/ml Intravenous Mallinckrodt Deutschland Gmb H 2016-09-20 2017-12-11 EU Optimark Injection, solution 500 micromol/ml Intravenous Mallinckrodt Deutschland Gmb H 2016-09-20 2017-12-11 EU Optimark Solution 330.9 mg / mL Intravenous Liebel Flarsheim Company Llc Not applicable Not applicable Canada 
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
- External Links
- Human Metabolome Database
- HMDB0014678
- KEGG Drug
- D01646
- PubChem Compound
- 444013
- PubChem Substance
- 46504481
- ChemSpider
- 392041
- 228833
- ChEBI
- 31644
- ChEMBL
- CHEMBL1200457
- PharmGKB
- PA164743703
- Wikipedia
- Gadoversetamide
- FDA label
- Download (925 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Pathological Processes 1 2 Completed Diagnostic Brain Disorders / Spinal Cord Diseases 1 Not Available Completed Basic Science Coronary Artery Disease (CAD) 1
Pharmacoeconomics
- Manufacturers
- Mallinckrodt inc
- Packagers
- Mallinckrodt Inc.
- Dosage Forms
Form Route Strength Injection Intravenous 100 mg Injection, solution Intravenous Injection, solution Intravenous 0.5 mmol/1mL Injection, solution Intravenous 500 micromol/ml Solution Intravenous 330.9 mg / mL Injection, solution Intravenous 500 μmol/ml - Prices
Unit description Cost Unit Optimark 330.9 mg/ml vial 4.49USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5130120 No 1992-07-14 2009-07-14 US 
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.98 mg/mL ALOGPS logP 0.36 ALOGPS logP -8.9 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 0.91 Chemaxon pKa (Strongest Basic) 8.34 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 206.77 Å2 Chemaxon Rotatable Bond Count 22 Chemaxon Refractivity 154.49 m3·mol-1 Chemaxon Polarizability 49.81 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9122 Blood Brain Barrier + 0.8868 Caco-2 permeable - 0.5196 P-glycoprotein substrate Substrate 0.7041 P-glycoprotein inhibitor I Non-inhibitor 0.6432 P-glycoprotein inhibitor II Non-inhibitor 0.9129 Renal organic cation transporter Non-inhibitor 0.8953 CYP450 2C9 substrate Non-substrate 0.8552 CYP450 2D6 substrate Non-substrate 0.8151 CYP450 3A4 substrate Non-substrate 0.5786 CYP450 1A2 substrate Non-inhibitor 0.9171 CYP450 2C9 inhibitor Non-inhibitor 0.8749 CYP450 2D6 inhibitor Non-inhibitor 0.9323 CYP450 2C19 inhibitor Non-inhibitor 0.8211 CYP450 3A4 inhibitor Non-inhibitor 0.9656 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9637 Ames test Non AMES toxic 0.7751 Carcinogenicity Non-carcinogens 0.8075 Biodegradation Not ready biodegradable 0.5115 Rat acute toxicity 2.0763 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9576 hERG inhibition (predictor II) Non-inhibitor 0.8903
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03di-2031901000-7138d3d3f1b5d5d82c31 - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 226.7123511 predictedDarkChem Lite v0.1.0 [M+H]+ 223.4432511 predictedDarkChem Lite v0.1.0 [M+Na]+ 225.6696511 predictedDarkChem Lite v0.1.0
Drug created at June 13, 2005 13:24 / Updated at April 17, 2024 06:33