Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H38N3O14P.Gd.3Na.H2O |
Molecular Weight | 975.87 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].[Na+].[Na+].[Gd+3].[O-]C(=O)CN(CCN(CC([O-])=O)CC([O-])=O)C[C@H](COP([O-])(=O)OC1CCC(CC1)(C2=CC=CC=C2)C3=CC=CC=C3)N(CC([O-])=O)CC([O-])=O
InChI
InChIKey=PIZALBORPSCYJU-QSQMUHTISA-H
InChI=1S/C33H44N3O14P.Gd.3Na.H2O/c37-28(38)18-34(15-16-35(19-29(39)40)20-30(41)42)17-26(36(21-31(43)44)22-32(45)46)23-49-51(47,48)50-27-11-13-33(14-12-27,24-7-3-1-4-8-24)25-9-5-2-6-10-25;;;;;/h1-10,26-27H,11-23H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48);;;;;1H2/q;+3;3*+1;/p-6/t26-;;;;;/m1...../s1
Molecular Formula | HO |
Molecular Weight | 17.0073 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Gd |
Molecular Weight | 157.25 |
Charge | 3 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C33H39N3O14P |
Molecular Weight | 732.6482 |
Charge | -5 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.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/2013/204781s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.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/
Gadobutrol is a second-generation extracellular non-ionic macrocyclic GBCA that is used in patients undergoing diagnostic contrast-enhanced MRI for visualization of pathological lesions in the CNS and all other body regions or for contrast-enhanced magnetic resonance angiography (MRA) to evaluate perfusion and flow-related abnormalities. It is a non-ionic, paramagnetic complex consisting of gadolinium (Gd3+) chelated with the macrocyclic compound dihydroxy-hydroxymethylpropyl-tetraazacyclododecane-triacetic acid (butrol). Gadavist (the trade name of gadobutrol) was approved by FDA in 2011 for intravenous use in diagnostic MRI in adults and children (2 years of age and older) to detect and visualize areas with disrupted blood brain barrier and/or abnormal vascularity of the central nervous system. Application of gadobutrol in humans, up to a dose of 0.5 mmol/kg was shown to be well tolerated. Following intravenous administration, gadobutrol may increase MRI sensitivity for the detection of tumors and inflammatory and demyelinating diseases of the central nervous system which are associated with areas with blood-brain barrier defects due to altered perfusion or an enlarged extracellular space. Gadobutrol is not metabolized. It is eliminated in an unchanged form via the kidneys; extra-renal elimination is negligible. Side effects include headache, nausea, abnormal taste and feeling hot.
CNS Activity
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.pdf
Curator's Comment: In rats, gadobutrol does not penetrate the intact blood-brain barrier
Originator
Sources: http://www.prnewswire.com/news-releases/fda-approves-dotarem-gadoterate-meglumine-first-macrocyclic-and-ionic-gadolinium-based-contrast-agent-in-usa-199354771.htmlhttps://www.ncbi.nlm.nih.gov/pubmed/7960618
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 |
---|---|---|---|---|
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 Date1.36373758E12 |
|||
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 Date1.30006083E12 |
|||
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 Date1.30006083E12 |
|||
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 Date1.30006083E12 |
PubMed
Title | Date | PubMed |
---|---|---|
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors. | 1997 May |
|
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations. | 2002 Jun 1 |
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Gadolinium-containing contrast media for radiographic examinations: a position paper. | 2002 Oct |
|
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium. | 2004 May |
|
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. | 2005 Apr 20 |
|
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C. | 2006 Apr 28 |
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Renal safety of gadolinium-based contrast agent for ionizing radiation imaging. | 2006 Jul |
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Gadolinium-based contrast agents and nephrotoxicity. | 2006 Nov |
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Gadolinium and kidney disease: are your patients at risk? | 2008 Mar-Apr |
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Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency. | 2009 Dec |
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Release of ATP from rat urinary bladder mucosa: role of acid, vanilloids and stretch. | 2009 Dec |
|
Large sample of nephrogenic systemic fibrosis cases from a single institution. | 2009 Oct |
|
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity. | 2010 Aug |
|
Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture. | 2010 Mar |
|
Toxicological safety evaluation of gadobutrol. | 2012 Nov |
|
MR Angiography at 3 T of Peripheral Arterial Disease: A Randomized Prospective Comparison of Gadoterate Meglumine and Gadobutrol. | 2015 Jun |
|
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging. | 2015 Mar |
|
MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T. | 2016 Mar |
Sample Use Guides
For adult and pediatric patients (2 years and older), the recommended dose of DOTAREM (gadoterate meglumine) is 0.2 mL/kg (0.1 mmol/kg) body weight administered as an intravenous bolus injection, manually or by power injector, at a flow rate of approximately 2 mL/second for adults and 1-2 mL/second for pediatric patients.
Route of Administration:
Intravenous
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:19:43 UTC 2023
by
admin
on
Wed Jul 05 23:19:43 UTC 2023
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Record UNII |
XM33Q67UVH
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Record Status |
Validated (UNII)
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Record Version |
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EMA ASSESSMENT REPORTS |
ABLAVAR (WITHDRAWN: RADIO RESONANCE PERFUSION)
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NCI_THESAURUS |
C62358
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100000089561
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Gadofosveset
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XM33Q67UVH
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DB06705
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1364289
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CHEMBL1908843
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SUB21051
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158440
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C81057
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211570-55-7
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DTXSID501027793
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |