U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N4O8.Gd.Na
Molecular Weight 580.62
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GADOTERATE SODIUM

SMILES

[Na+].[Gd+3].[O-]C(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1

InChI

InChIKey=VIFBVOSDYUIKIK-UHFFFAOYSA-J
InChI=1S/C16H28N4O8.Gd.Na/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;+1/p-4

HIDE SMILES / InChI

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 C16H24N4O8
Molecular Weight 400.3838
Charge -4
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

Description
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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P27169
Gene ID: 5444.0
Gene Symbol: PON1
Target Organism: Homo sapiens (Human)
105.0 mM [Ki]
Target ID: P52209
Gene ID: 5226.0
Gene Symbol: PGD
Target Organism: Homo sapiens (Human)
73.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
DOTAREM

Approved Use

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.

Launch Date

2013
Diagnostic
GADAVIST

Approved Use

Gadavist 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 Date

2011
Diagnostic
GADAVIST

Approved Use

Gadavist 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 Date

2011
Diagnostic
GADAVIST

Approved Use

Gadavist 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 Date

2011
PubMed

PubMed

TitleDatePubMed
Aluminum-induced DNA synthesis in osteoblasts: mediation by a G-protein coupled cation sensing mechanism.
1994 Sep
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.
1997 May
Aluminum is a weak agonist for the calcium-sensing receptor.
1999 May
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
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow.
2001 Feb 9
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.
2006 Apr 28
Loss of primary cilia results in deregulated and unabated apical calcium entry in ARPKD collecting duct cells.
2006 Jun
Gadolinium-based contrast media for multi-detector row spiral CT pulmonary angiography in patients with renal insufficiency.
2006 Mar
Suggesting gadolinium-based contrast media for CT in azotemic patients is not based on historical, clinical, and experimental data.
2007 Aug
Gadolinium contrast may be risky in kidney disease.
2007 Jun 30
Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue.
2008 Apr
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.
2008 Jul
Gadolinium and kidney disease: are your patients at risk?
2008 Mar-Apr
Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency.
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
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.
2011 Feb 18
Heavy metal cations permeate the TRPV6 epithelial cation channel.
2011 Jan
Toxicological safety evaluation of gadobutrol.
2012 Nov
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.
2013 Apr
Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats.
2015 Dec
MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T.
2016 Mar
Patents

Sample Use Guides

Recommended dose for adults and pediatric patients (including term neonates) is 0.1 mL/kg body weight. Administer as an intravenous bolus injection. Follow injection with a normal saline flush.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:04:58 GMT 2023
Edited
by admin
on Fri Dec 15 18:04:58 GMT 2023
Record UNII
99J2XUF1JT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GADOTERATE SODIUM
Common Name English
GD-DOTA
Common Name English
Gadoterate sodium [WHO-DD]
Common Name English
GADOLINATE(1-), (1,4,7,10-TETRAAZACYCLODODECANE-1,4,7,10-TETRAACETATO(4-)-.KAPPA.N1,.KAPPA.N4,.KAPPA.N7,.KAPPA.N10,.KAPPA.O1,.KAPPA.O4,.KAPPA.O7,.KAPPA.O10)-, SODIUM (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
99J2XUF1JT
Created by admin on Fri Dec 15 18:04:59 GMT 2023 , Edited by admin on Fri Dec 15 18:04:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID10918889
Created by admin on Fri Dec 15 18:04:59 GMT 2023 , Edited by admin on Fri Dec 15 18:04:59 GMT 2023
PRIMARY
SMS_ID
300000046474
Created by admin on Fri Dec 15 18:04:59 GMT 2023 , Edited by admin on Fri Dec 15 18:04:59 GMT 2023
PRIMARY
PUBCHEM
122152
Created by admin on Fri Dec 15 18:04:59 GMT 2023 , Edited by admin on Fri Dec 15 18:04:59 GMT 2023
PRIMARY
CHEBI
73732
Created by admin on Fri Dec 15 18:04:59 GMT 2023 , Edited by admin on Fri Dec 15 18:04:59 GMT 2023
PRIMARY
CAS
92923-44-9
Created by admin on Fri Dec 15 18:04:59 GMT 2023 , Edited by admin on Fri Dec 15 18:04:59 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY