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Gadoxetic acid
Identification
- Name
- Gadoxetic acid
- Accession Number
- DB08884
- Description
Gadoxetic acid (gadoxetate) is a paramagnetic gadolinium-containing contrast agent in which its salt form, gadoxetate disodium, is used for intravenous injection. Ethoxybenzyl diethylenetriaminepentaacetic acid is the moiety that chelates with a gadolinium ion and forms a stable complex with it to make up the drug. It is marketed by Bayer HealthCare Pharmaceuticals and FDA approved on July 3, 2008.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gadoxetic acid (DB08884)
- Weight
- Average: 681.75
Monoisotopic: 682.11214 - Chemical Formula
- C23H30GdN3O11
- Synonyms
- Gadoxetate
- Gadoxetic acid
- Gd-EOB-DTPA
Pharmacology
- Indication
Gadoxetate is used as a contrast medium for magnetic resonance imaging (MRI) to detect and characterize lesions in the liver.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Gadoxetate disodium is an amphipathic compound in which gadoxetate is hydrophillic and its moiety, the ethoxybenyzl group, is lipophillic. Consequently, gadoxetate disodium has a biphasic mode of action in which it first distributes into the extracellular space after bolus injection and then hepatocytes selectively takes up the drug.
- Mechanism of action
When gadoxetate disodium is placed in an external magnetic field, a large magnetic moment is produced. As a result, a magnetic field is induced around the tissue. The water protons in the vicinity are disrupted such that the change the proton density and spin characteristics are detected and visualized by a device.
- Absorption
- Not Available
- Volume of distribution
Total volume of distribution at steady state is 0.21 L/kg. Gadoxetate disodium cannot diffuse through the blood brain barrier. The two transporters that gadoxetate disodium can enter the hepatocyte through are OATP1B1 and OATP1B3. Gadoxetate disodium may also exit the heptaocyte and go back into sinusoidal space via active transport through multidrug resistance protein 3 and 4.
- Protein binding
<10% protein bound. Because it is more protein bound than other gadolinium-based contrast agents, gadoxetate disodium has increased T1 relaxivity. This results in an enhancement of the signal.
- Metabolism
Gadoxetate disodium is not metabolized.
- Route of elimination
Gadoxetate disodium is eliminated equally via urine and feces. Multidrug resistance protein 2 actively transports/excretes gadoxetate disodium into the bile.
- Half-life
Terminal elimination half-life, healthy subjects, adults = 0.91 - 0.95 hours
- Clearance
Clearance may be lower in older patients. Total serum clearance (CLtot) = 250 mL/min; Renal clearance (CLr) = 120 mL/min
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50, oral, rat = 18100 mg/kg; LD50, oral, mouse = 14500 mg/kg; LD50, IV, rat = 3600 - 7300 mg/kg; LD50, IV, mouse = 5400 - 10900 mg/kg; LD50, IV, dog = >2200 mg/kg
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAcetylcysteine The excretion of Gadoxetic acid can be decreased when combined with Acetylcysteine. Aminohippuric acid The excretion of Gadoxetic acid can be decreased when combined with Aminohippuric acid. Amprenavir The excretion of Gadoxetic acid can be decreased when combined with Amprenavir. Apalutamide The excretion of Gadoxetic acid can be increased when combined with Apalutamide. Asunaprevir The excretion of Gadoxetic acid can be decreased when combined with Asunaprevir. Ataluren The excretion of Gadoxetic acid can be decreased when combined with Ataluren. Atazanavir The excretion of Gadoxetic acid can be decreased when combined with Atazanavir. Atorvastatin The excretion of Gadoxetic acid can be decreased when combined with Atorvastatin. Axitinib The excretion of Gadoxetic acid can be decreased when combined with Axitinib. Baricitinib The excretion of Gadoxetic acid can be decreased when combined with Baricitinib. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Gadoxetate disodium HOY74VZE0M 135326-22-6 SLYTULCOCGSBBJ-UHFFFAOYSA-I - 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 Unlock Additional DataEovist Injection, solution 181.43 mg/1mL Intravenous Bayer HealthCare Pharmaceuticals Inc. 2008-07-03 Not applicable US 
Primovist Solution Intravenous Bayer 2010-02-04 Not applicable Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- V08CA10 — Gadoxetic acid
- Drug Categories
- Acetates
- Acids, Acyclic
- Amines
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Fatty Acids
- Fatty Acids, Volatile
- Gadolinium-based Contrast Agent
- Lipids
- Magnetic Resonance Contrast Activity
- Magnetic Resonance Imaging Contrast Media
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- Organometallic Compounds
- Other Diagnostics
- Paramagnetic Contrast Agent
- Paramagnetic Contrast Media
- Polyamines
- Classification
- Not classified
Chemical Identifiers
- UNII
- 3QJA87N40S
- CAS number
- 135326-11-3
- InChI Key
- PCZHWPSNPWAQNF-LMOVPXPDSA-K
- InChI
- InChI=1S/C23H33N3O11.Gd/c1-2-37-18-5-3-16(4-6-18)9-17(26(14-22(33)34)15-23(35)36)10-24(11-19(27)28)7-8-25(12-20(29)30)13-21(31)32;/h3-6,17H,2,7-15H2,1H3,(H,27,28)(H,29,30)(H,31,32)(H,33,34)(H,35,36);/q;+3/p-3/t17-;/m0./s1
- IUPAC Name
- gadolinium(3+) ion 2-[(2-{[(2S)-2-[bis(carboxymethyl)amino]-3-(4-ethoxyphenyl)propyl](carboxylatomethyl)amino}ethyl)(carboxylatomethyl)amino]acetate
- SMILES
- [Gd+3].[H][C@@](CN(CCN(CC([O-])=O)CC([O-])=O)CC([O-])=O)(CC1=CC=C(OCC)C=C1)N(CC(O)=O)CC(O)=O
References
- General References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [PubMed:22504332]
- External Links
- KEGG Drug
- D04288
- PubChem Compound
- 131704314
- PubChem Substance
- 175427133
- ChemSpider
- 189907
- 802624
- ChEMBL
- CHEMBL1201768
- PharmGKB
- PA165985534
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Gadoxetic_acid
- AHFS Codes
- 36:89.00* — Other Diagnostics
- FDA label
- Download (223 KB)
- MSDS
- Download (114 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Diagnostic Liver Cirrhosis 1 4 Completed Diagnostic Contrast Media 1 4 Completed Diagnostic Hepatocellular Carcinoma 1 4 Completed Diagnostic Transient Severe Arterial Phase Motion 1 4 Not Yet Recruiting Other Cognitive Function / Contrast Media / Motor Function 1 4 Not Yet Recruiting Treatment Metastatic Hepatic Cancer / Primary Liver Cancers 1 3 Completed Diagnostic Known or Suspected Focal Liver Lesions 1 3 Terminated Diagnostic Magnetic Resonance Imaging (MRI) 1 2 Completed Diagnostic Prostate Cancer 1 1 Completed Diagnostic Adult Hepatocellular Carcinoma / Advanced Adult Hepatocellular Carcinoma / BCLC Stage 0 Adult Hepatocellular Carcinoma / BCLC Stage A Adult Hepatocellular Carcinoma / BCLC Stage B Adult Hepatocellular Carcinoma / BCLC Stage C Adult Hepatocellular Carcinoma / BCLC Stage D Adult Hepatocellular Carcinoma / Localized Non-Resectable Adult Liver Carcinoma / Localized Resectable Adult Liver Carcinoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 181.43 mg/1mL Solution Intravenous - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6039931 No 2000-03-21 2021-11-13 US US5798092 No 1998-08-25 2015-08-25 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source pKa 6.8-8 MSDS - Predicted Properties
Property Value Source Water Solubility 0.497 mg/mL ALOGPS logP 1.24 ALOGPS logP -4.3 ChemAxon logS -3.2 ALOGPS pKa (Strongest Acidic) 1.98 ChemAxon pKa (Strongest Basic) 9.99 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 213.94 Å2 ChemAxon Rotatable Bond Count 20 ChemAxon Refractivity 159.21 m3·mol-1 ChemAxon Polarizability 50.67 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
Property Value Probability Human Intestinal Absorption + 0.6058 Blood Brain Barrier + 0.6251 Caco-2 permeable - 0.5137 P-glycoprotein substrate Substrate 0.6927 P-glycoprotein inhibitor I Non-inhibitor 0.6538 P-glycoprotein inhibitor II Non-inhibitor 0.9495 Renal organic cation transporter Non-inhibitor 0.6488 CYP450 2C9 substrate Non-substrate 0.8375 CYP450 2D6 substrate Non-substrate 0.8177 CYP450 3A4 substrate Non-substrate 0.6054 CYP450 1A2 substrate Non-inhibitor 0.6386 CYP450 2C9 inhibitor Non-inhibitor 0.7982 CYP450 2D6 inhibitor Non-inhibitor 0.6855 CYP450 2C19 inhibitor Non-inhibitor 0.781 CYP450 3A4 inhibitor Non-inhibitor 0.9528 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7762 Ames test Non AMES toxic 0.6871 Carcinogenicity Non-carcinogens 0.8385 Biodegradation Not ready biodegradable 0.6465 Rat acute toxicity 2.2477 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Non-inhibitor 0.7809
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Nassif A, Jia J, Keiser M, Oswald S, Modess C, Nagel S, Weitschies W, Hosten N, Siegmund W, Kuhn JP: Visualization of hepatic uptake transporter function in healthy subjects by using gadoxetic acid-enhanced MR imaging. Radiology. 2012 Sep;264(3):741-50. doi: 10.1148/radiol.12112061. Epub 2012 Jul 6. [PubMed:22771883]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Nassif A, Jia J, Keiser M, Oswald S, Modess C, Nagel S, Weitschies W, Hosten N, Siegmund W, Kuhn JP: Visualization of hepatic uptake transporter function in healthy subjects by using gadoxetic acid-enhanced MR imaging. Radiology. 2012 Sep;264(3):741-50. doi: 10.1148/radiol.12112061. Epub 2012 Jul 6. [PubMed:22771883]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
- Gene Name
- ABCC3
- Uniprot ID
- O15438
- Uniprot Name
- Canalicular multispecific organic anion transporter 2
- Molecular Weight
- 169341.14 Da
References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [PubMed:22504332]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- Canalicular multispecific organic anion transporter 1
- Molecular Weight
- 174205.64 Da
References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [PubMed:22504332]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- May be an organic anion pump relevant to cellular detoxification.
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [PubMed:22504332]
Drug created on May 22, 2013 15:49 / Updated on August 05, 2020 23:35
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