Gadoteric acid
Identification
- Name
- Gadoteric acid
- Accession Number
- DB09132
- Description
Gadoteric acid is a macrocycle-structured gadolinium-based MRI contrast agent. It is composed of the organic acid DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) used for its chelating properties, and gadolinium (Gd3+). As a paramagnetic molecule, gadoterate develops a magnetic moment when placed in a magnetic field. This magnetic moment enhances the relaxation rates of water protons in its vicinity, leading to an increase in signal intensity (brightness) of tissues. More specifically, it reduces the T1 relaxation time (and to some extent the T2 and T2* relaxation times) in NMR, which is the source of its clinical utility. Increased signal brightness allows it to be used in imaging of blood vessels and of inflamed or diseased tissue where the blood vessels become 'leaky'.
Gadoteric acid, as the FDA approved product Dotarem, is indicated for intravenous use with magnetic resonance imaging (MRI) in brain (intracranial), spine and associated tissues in adult and pediatric patients (2 years of age and older) to detect and visualize areas with disruption of the blood brain barrier (BBB) and/or abnormal vascularity.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gadoteric acid (DB09132)
- Weight
- Average: 558.65
Monoisotopic: 559.09135 - Chemical Formula
- C16H25GdN4O8
- Synonyms
- [2,2',2'',2'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl-κ4N1,N4,N7,N10)tetraacetato(3−)]gadolinium
- DOTA-Gd
- Gadoterate
- Gadoteric acid
- Gd-DOTA
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
Gadoteric acid is indicated for intravenous use with magnetic resonance imaging (MRI) in brain (intracranial), spine and associated tissues in adult and pediatric patients (2 years of age and older) to detect and visualize areas with disruption of the blood brain barrier (BBB) and/or abnormal vascularity.
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Gadoterate affects proton relaxation times and consequently the MR signal, and the contrast obtained is characterized by the relaxivity of the gadoterate molecule. The relaxivity values for gadoterate are similar across the spectrum of magnetic field strengths used in clinical MRI (0.2 - 1.5 T). Gadoterate does not cross the intact blood-brain barrier and, therefore, does not enhance normal brain or lesions that have a normal blood-brain barrier, e.g. cysts, mature post-operative scars. However, disruption of the blood-brain barrier or abnormal vascularity allows distribution of gadoterate in lesions such as neoplasms, abscesses, and infarcts.
- Mechanism of action
Gadoterate is a paramagnetic molecule that develops a magnetic moment when placed in a magnetic field. The magnetic moment enhances the relaxation rates of water protons in its vicinity, leading to an increase in signal intensity (brightness) of tissues. When placed in a magnetic field, gadoterate shortens the T1 and T2 relaxation times in target tissues.
- Absorption
- Not Available
- Volume of distribution
The volume of distribution at steady state of total gadolinium in normal subjects is 179 and 211 mL/kg in female and male subjects respectively, roughly equivalent to that of extracellular water.
- Protein binding
Gadoterate does not undergo protein binding in vitro.
- Metabolism
Gadoterate is not known to be metabolized.
- Route of elimination
Gadoteric acid is excreted primarily in urine.
- Half-life
Gadoteric acid demonstrates a mean elimination half-life of about 1.4 hr and 2.0 hr in female and male subjects, respectively.
- Clearance
In healthy subjects, the renal and total clearance rates of total gadolinium are comparable (1.27 and 1.74 mL/min/kg in females; and 1.40 and 1.64 mL/min/kg in males, respectively).
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
The most frequent adverse reactions in clinical studies were nausea, headache, injection site pain, injection site coldness, and burning sensation. Nephrogenic Systemic Fibrosis has occurred in patients with impaired elimination of GBCAs.
- Affected organisms
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Gadoteric acid which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Acrivastine Gadoteric acid may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Gadoteric acid which could result in a higher serum level. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Gadoterate meglumine L0ND3981AG 92943-93-6 RYHQMKVRYNEBNJ-BMWGJIJESA-K - 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 Dotarem Solution 376.9 mg Intravenous Guerbet 2017-09-22 Not applicable Canada 
Dotarem Injection 376.9 mg/1mL Intravenous Guerbet LLC 2019-09-18 Not applicable US 
Dotarem Injection 376.9 mg/1mL Intravenous Guerbet LLC 2013-04-26 Not applicable US Dotarem Injection 376.9 mg/1mL Intravenous Guerbet LLC 2013-04-26 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Clariscan Injection, solution 376.9 mg/1mL Intravenous Ge Healthcare 2019-11-01 Not applicable US
Categories
- ATC Codes
- V08CA02 — Gadoteric acid
- Drug Categories
- Alcohols
- Amino Sugars
- Carbohydrates
- Chelating Agents
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Gadolinium-based Contrast Agent
- Hexosamines
- Magnetic Resonance Imaging Contrast Media
- Other Diagnostics
- Paramagnetic Contrast Media
- Sequestering Agents
- Sugar Alcohols
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Tetracarboxylic acids and derivatives
- Direct Parent
- Tetracarboxylic acids and derivatives
- Alternative Parents
- Alpha amino acids / Trialkylamines / Carboxylic acid salts / Amino acids / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic zwitterions / Organic salts / Organic oxides show 2 more
- Substituents
- Aliphatic heteromonocyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid salt show 13 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- gadolinium coordination entity (CHEBI:73732)
Chemical Identifiers
- UNII
- QVF9Y6955W
- CAS number
- 72573-82-1
- InChI Key
- GFSTXYOTEVLASN-UHFFFAOYSA-K
- InChI
- InChI=1S/C16H28N4O8.Gd/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26;/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28);/q;+3/p-3
- IUPAC Name
- gadolinium(3+) ion 2-[4,7-bis(carboxylatomethyl)-10-(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetate
- SMILES
- [Gd+3].OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D08007
- PubChem Compound
- 158536
- PubChem Substance
- 310265047
- ChemSpider
- 139460
- ChEBI
- 73732
- ChEMBL
- CHEMBL3833326
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Gadoteric_acid
- AHFS Codes
- 36:89.00* — Other Diagnostics
- FDA label
- Download (3.85 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Diagnostic Renal Dysfunction 1 4 Completed Not Available Arterial Occlusive Diseases 1 4 Completed Diagnostic Brain Diseases 1 4 Completed Diagnostic Coronary Artery Atherosclerosis / Type 2 Diabetes Mellitus 1 4 Completed Diagnostic Impaired kidney function 1 4 Completed Diagnostic Magnetic Resonance Imaging (MRI) 2 4 Completed Diagnostic Neoplastic CNS Lesions 1 4 Completed Diagnostic Peripheral Arterial Disease (PAD) 1 4 Completed Diagnostic Primary Brain Tumors 1 4 Completed Diagnostic Transient Severe Arterial Phase Motion 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intra-articular Injection, solution Intravenous 376.9 mg/1mL Solution Intravenous Injection, solution Parenteral Injection Intravenous Injection, solution Intramuscular Injection Intravenous 376.9 mg/1mL Solution Intravenous 376.9 mg Solution Intravenous 377 mg/1ml Injection, solution Intravenous Injection, solution - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 12.8 mg/mL ALOGPS logP 0.23 ALOGPS logP -7.7 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 0.47 ChemAxon pKa (Strongest Basic) 10.08 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 170.65 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 128.93 m3·mol-1 ChemAxon Polarizability 38.15 Å3 ChemAxon Number of Rings 1 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Drug created on September 29, 2015 19:58 / Updated on April 12, 2021 12:00