Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H28N3O11.Gd.2H |
Molecular Weight | 681.75 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[H+].[Gd+3].CCOC1=CC=C(C[C@@H](CN(CCN(CC([O-])=O)CC([O-])=O)CC([O-])=O)N(CC([O-])=O)CC([O-])=O)C=C1
InChI
InChIKey=PCZHWPSNPWAQNF-LMOVPXPDSA-K
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
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7960618; https://www.ncbi.nlm.nih.gov/pubmed/?term=23435930; http://mnoncology.com/disease-drug-info/drug-dictionary/G/
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7960618; https://www.ncbi.nlm.nih.gov/pubmed/?term=23435930; http://mnoncology.com/disease-drug-info/drug-dictionary/G/
DOTAREM (Gadoterate Meglumine ) is a gadolinium-based contrast agent indicated for intravenous use with magnetic resonance imaging (MRI) in brain (intracranial), spine and associatedtissues 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. Gadoterate Meglumine is a gadolinium chelate paramagnetic contrast agent. When placed in a magnetic field, gadoterate meglumine produces a large magnetic moment and so a large local magnetic field, which can enhance the relaxation rate of nearby protons; as a result, the signal intensity of tissue images observed with magnetic resonance imaging (MRI) may be enhanced. Because this agent is preferentially taken up by normal functioning hepatocytes, normal hepatic tissue is enhanced with MRI while tumor tissue is unenhanced. In addition, because gadobenate dimeglumine is excreted in the bile, it may be used to visualize the biliary system using MRI.
CNS Activity
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdf
Curator's Comment: 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 bloodbrain barrier or abnormal vascularity allows distribution of gadoterate in lesions such as neoplasms, abscesses, and infarcts.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7960618http://www.prnewswire.com/news-releases/fda-approves-dotarem-gadoterate-meglumine-first-macrocyclic-and-ionic-gadolinium-based-contrast-agent-in-usa-199354771.html
Curator's Comment: # Schering AG (now subsidiary of Bayer)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P27169 Gene ID: 5444.0 Gene Symbol: PON1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/31179770 |
105.0 mM [Ki] | ||
Target ID: P52209 Gene ID: 5226.0 Gene Symbol: PGD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20235752 |
73.0 mM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | DOTAREM Approved UseIndicated 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. Launch Date2013 |
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Diagnostic | GADAVIST Approved UseGadavist is a gadolinium-based contrast agent indicated for use with magnetic resonance imaging to detect and visualize areas with disrupted blood brain barrier and/or abnormal vascularity of the central nervous system in adult and pediatric patients (including term neonates); to assess the presence and extent of malignant breast disease; to evaluate known or suspected supra-aortic or renal artery disease in adult and pediatric patients (including term neonates) disease. Launch Date2011 |
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Diagnostic | GADAVIST Approved UseGadavist is a gadolinium-based contrast agent indicated for use with magnetic resonance imaging to detect and visualize areas with disrupted blood brain barrier and/or abnormal vascularity of the central nervous system in adult and pediatric patients (including term neonates); to assess the presence and extent of malignant breast disease; to evaluate known or suspected supra-aortic or renal artery disease in adult and pediatric patients (including term neonates) disease. Launch Date2011 |
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Diagnostic | GADAVIST Approved UseGadavist is a gadolinium-based contrast agent indicated for use with magnetic resonance imaging to detect and visualize areas with disrupted blood brain barrier and/or abnormal vascularity of the central nervous system in adult and pediatric patients (including term neonates); to assess the presence and extent of malignant breast disease; to evaluate known or suspected supra-aortic or renal artery disease in adult and pediatric patients (including term neonates) disease. Launch Date2011 |
PubMed
Title | Date | PubMed |
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Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors. | 1997 May |
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Aluminum is a weak agonist for the calcium-sensing receptor. | 1999 May |
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The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel. | 2001 Feb 16 |
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Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow. | 2001 Feb 9 |
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Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations. | 2002 Jun 1 |
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Diacylglycerol activates the influx of extracellular cations in T-lymphocytes independently of intracellular calcium-store depletion and possibly involving endogenous TRP6 gene products. | 2002 May 15 |
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Gadolinium-containing contrast media for radiographic examinations: a position paper. | 2002 Oct |
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A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium. | 2004 May |
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Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. | 2005 Apr 20 |
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Gadolinium-based contrast agents and nephrotoxicity in patients undergoing coronary artery procedures. | 2006 Feb |
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Renal safety of gadolinium-based contrast agent for ionizing radiation imaging. | 2006 Jul |
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Loss of primary cilia results in deregulated and unabated apical calcium entry in ARPKD collecting duct cells. | 2006 Jun |
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Gadolinium-based contrast agents and nephrotoxicity. | 2006 Nov |
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Suggesting gadolinium-based contrast media for CT in azotemic patients is not based on historical, clinical, and experimental data. | 2007 Aug |
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Gadolinium contrast may be risky in kidney disease. | 2007 Jun 30 |
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Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue. | 2008 Apr |
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Quantification of gadolinium in nephrogenic systemic fibrosis: re-examination of a reported cohort with analysis of clinical factors. | 2008 Aug |
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Gadolinium and kidney disease: are your patients at risk? | 2008 Mar-Apr |
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Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry. | 2008 Nov 1 |
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Renal failure and gadolinium. The number of documented cases is rising. | 2008 Oct |
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Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency. | 2009 Dec |
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Large sample of nephrogenic systemic fibrosis cases from a single institution. | 2009 Oct |
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Heavy metal cations permeate the TRPV6 epithelial cation channel. | 2011 Jan |
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Toxicological safety evaluation of gadobutrol. | 2012 Nov |
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Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children. | 2013 Apr |
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Tumor Detection at 3 Tesla with an Activatable Cell Penetrating Peptide Dendrimer (ACPPD-Gd), a T1 Magnetic Resonance (MR) Molecular Imaging Agent. | 2015 |
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Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats. | 2015 Dec |
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MR Angiography at 3 T of Peripheral Arterial Disease: A Randomized Prospective Comparison of Gadoterate Meglumine and Gadobutrol. | 2015 Jun |
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Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging. | 2015 Mar |
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The Benefits of High Relaxivity for Brain Tumor Imaging: Results of a Multicenter Intraindividual Crossover Comparison of Gadobenate Dimeglumine with Gadoterate Meglumine (The BENEFIT Study). | 2015 Sep |
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MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T. | 2016 Mar |
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NCI_THESAURUS |
C62358
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WHO-VATC |
QV08CA10
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V08CA10
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NDF-RT |
N0000175862
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NDF-RT |
N0000180184
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CHEMBL2221312
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219084
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802624
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3259
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C77549
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DB08884
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100000084490
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GADOXETIC ACID
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7226
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m5630
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135326-11-3
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Gadoxetate
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SUB07868MIG
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DTXSID90928961
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ACTIVE MOIETY
SUBSTANCE RECORD