Identification
- Summary
Gadoteridol is a medication used to improve the contrast of MRI scans for better visualization.
- Brand Names
- Prohance
- Generic Name
- Gadoteridol
- DrugBank Accession Number
- DB00597
- Background
Gadoteridol provides contrast enhancement of the brain, spine and surrounding tissues resulting in improved visualization (compared with unenhanced MRI) of lesions with abnormal vascularity or those thought to cause a disruption of the normal blood brain barrier. Gadoteridol can also be used for whole body contrast enhanced MRI including the head, neck, liver, breast, musculoskeletal system and soft tissue pathologies. n MRI, visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadoteridol shortens the T1 relaxation time in tissues where it accumulates. Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadoteridol in lesions such as neoplasms, abscesses, and subacute infarcts.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Gadoteridol (DB00597)
- Weight
- Average: 558.68
Monoisotopic: 559.127724835 - Chemical Formula
- C17H29GdN4O7
- Synonyms
- gadolinium 2,2',2''-[10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]triacetate
- gadolinium-HP-DO3A
- Gadoteridol
- Gadoteridolum
- GD-HP-DO 3A
- Gd-HPDO3A
- External IDs
- Gd-HP-DO 3A
- SQ 32692
Pharmacology
- Indication
Gadoteridol is indicated for use with magnetic resonance imaging (MRI) in order to visualize lesions with disrupted blood-brain barrier and/or abnormal vascularity in the brain, spine, and associated tissues in adult and pediatric patients, including term neonates.1 It is also indicated for visualization of lesions in the head and neck in adult patients.1
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- 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. Paramagnetic agents have unpaired electrons that generate a magnetic field about 700 times larger than the proton's field, thus disturbing the proton's local magnetic field. When the local magnetic field around a proton is disturbed its relaxation process is altered. MR images are based on proton density and proton relaxation dynamics. MR instruments can record two different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and T2 (spin-spin or transverse relaxation time). In MRI, visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadoteridol shortens the T1 relaxation time in tissues where it accumulates. Gadoteridol does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in central nervous system (CNS) lesions that have not caused an abnormal blood-brain barrier (e.g., cysts, mature post-operative scars). Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadoteridol in lesions such as neoplasms, abscesses, and subacute infarcts.
- Absorption
Not Available
- Volume of distribution
- 204 ± 58 mL/kg
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Gadoteridol is eliminated in the urine with 94.4 ± 4.8% (mean ± SD) of the dose excreted within 24 hours post-injection.
- Half-life
Distribution 12 minutes (mean), elimination 100 minutes (mean).
- Clearance
- 1.50+/- 0.35 mL/ min/kg
- renal cl=1.41 +/- 0.33 mL/ min/kg
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Gadoteridol may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Gadoteridol which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Gadoteridol which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Gadoteridol which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Gadoteridol which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Gadoteridol which could result in a higher serum level. Aclidinium Gadoteridol may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Gadoteridol may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Gadoteridol which could result in a higher serum level. Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Gadoteridol which could result in a higher serum level. 
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- 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.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ProHance Injection, solution 279.3 mg/1mL Intravenous BIPSO GmbH 1992-11-16 2016-11-09 US 
ProHance Injection, solution 279.3 mg/1mL Intravenous Bracco Diagnostics Inc 1992-11-16 Not applicable US Prohance - Liq IV 279.3mg/ml Solution 279.3 mg / mL Intravenous Bracco Imaging S.P.A. 1998-09-08 Not applicable Canada 
Prohance Liq IV 279.3mg/ml Liquid 279.3 mg / mL Intravenous Squibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc. 1993-12-31 1998-07-30 Canada
Categories
- ATC Codes
- V08CA04 — Gadoteridol
- Drug Categories
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Elements
- Lanthanoid Series Elements
- Magnetic Resonance Contrast Activity
- Magnetic Resonance Imaging Contrast Media
- Metals
- Metals, Rare Earth
- Other Diagnostics
- Paramagnetic Contrast Agent
- Paramagnetic Contrast Media
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
- 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 acids
- Alternative Parents
- Tricarboxylic acids and derivatives / Trialkylamines / Secondary alcohols / Carboxylic acid salts / Amino acids / 1,2-aminoalcohols / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic zwitterions show 4 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Aliphatic heteromonocyclic compound / Alpha-amino acid / Amine / Amino acid / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid salt show 14 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- gadolinium coordination entity (CHEBI:31643)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0199MV609F
- CAS number
- 120066-54-8
- InChI Key
- DPNNNPAKRZOSMO-UHFFFAOYSA-K
- InChI
- InChI=1S/C17H32N4O7.Gd/c1-14(22)10-18-2-4-19(11-15(23)24)6-8-21(13-17(27)28)9-7-20(5-3-18)12-16(25)26;/h14,22H,2-13H2,1H3,(H,23,24)(H,25,26)(H,27,28);/q;+3/p-3
- IUPAC Name
- gadolinium(3+) 2-[4,7-bis(carboxylatomethyl)-10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetate
- SMILES
- [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1
References
- General References
- FDA Approved Drug Products: Prohance (gadoteridol) injection for intravenous administration [Link]
- External Links
- Human Metabolome Database
- HMDB0014735
- KEGG Drug
- D01137
- PubChem Compound
- 60714
- PubChem Substance
- 46505738
- ChemSpider
- 54719
- 25483
- ChEBI
- 31643
- ChEMBL
- CHEMBL1200593
- PharmGKB
- PA164746463
- Wikipedia
- Gadoteridol
- FDA label
- Download (195 KB)
- MSDS
- Download (60.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Brain Disorders 1 4 Completed Diagnostic Coronary Artery Disease (CAD) / Type 1 Diabetes Mellitus 1 4 Recruiting Other Cognitive Functioning / Contrast Medium / Motor Function 1 3 Completed Diagnostic Brain Metastases 1 3 Completed Diagnostic Central Nervous System Disorder / Imaging procedure 1 1 Active Not Recruiting Treatment Anaplastic Astrocytoma (AA) / Glioblastoma Multiforme (GBM) / High Grade Glioma (HGG) / Malignant Glioma 1 0 Recruiting Diagnostic Multiple Sclerosis / Secondary Progressive Multiple Sclerosis (SPMS) 1 Not Available Active Not Recruiting Not Available Multiple Sclerosis 1 Not Available Completed Not Available Central Nervous System Disorder / Central Nervous System Neoplasm 1 Not Available Completed Diagnostic Glioblastoma Multiforme (GBM) 1
Pharmacoeconomics
- Manufacturers
- Bracco diagnostics inc
- Packagers
- Bracco Diagnostics Inc.
- Nycomed Inc.
- Dosage Forms
Form Route Strength Injection, solution Intravenous Injection, solution Intravenous 279.3 mg/1mL Injection, solution Intravenous 279.3 MG/ML Solution Intravenous 279.3 mg Injection, solution Parenteral Solution Intravenous 279.3 mg / mL Liquid Intravenous 279.3 mg / mL - Prices
Unit description Cost Unit Prohance 279.3 mg/ml vial 6.81USD 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 US5474756 No 1995-12-12 2012-12-12 US CA1341176 No 2001-01-30 2018-01-30 Canada US5846519 No 1998-12-08 2015-12-08 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 11.2 mg/mL ALOGPS logP 0.36 ALOGPS logP -6.8 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 1.46 Chemaxon pKa (Strongest Basic) 8.3 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 153.58 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 133.55 m3·mol-1 Chemaxon Polarizability 39.38 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 - 0.8097 Blood Brain Barrier + 0.6442 Caco-2 permeable - 0.5567 P-glycoprotein substrate Substrate 0.7825 P-glycoprotein inhibitor I Non-inhibitor 0.8295 P-glycoprotein inhibitor II Non-inhibitor 0.8408 Renal organic cation transporter Non-inhibitor 0.8026 CYP450 2C9 substrate Non-substrate 0.8605 CYP450 2D6 substrate Non-substrate 0.769 CYP450 3A4 substrate Non-substrate 0.6437 CYP450 1A2 substrate Non-inhibitor 0.8814 CYP450 2C9 inhibitor Non-inhibitor 0.8843 CYP450 2D6 inhibitor Non-inhibitor 0.8737 CYP450 2C19 inhibitor Non-inhibitor 0.81 CYP450 3A4 inhibitor Non-inhibitor 0.908 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9838 Ames test Non AMES toxic 0.7586 Carcinogenicity Non-carcinogens 0.9134 Biodegradation Not ready biodegradable 0.6054 Rat acute toxicity 2.1688 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6113 hERG inhibition (predictor II) Non-inhibitor 0.8966
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at June 13, 2005 13:24 / Updated at March 21, 2023 17:58