GADOXETATE DISODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H28N3O11.Gd.2Na
Molecular Weight	725.71
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].[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=SLYTULCOCGSBBJ-FCQHKQNSSA-I

InChI=1S/C23H33N3O11.Gd.2Na/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;2*+1/p-5/t17-;;;/m0.../s1

HIDE SMILES / InChI

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serum paraoxonase/arylesterase 1 31 Target ID: P27169 Gene ID: 5444.0 Gene Symbol: PON1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/31179770	Inhibitor 8297		105.0 mM [Ki]
6-phosphogluconate dehydrogenase, decarboxylating 29 Target ID: P52209 Gene ID: 5226.0 Gene Symbol: PGD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20235752	Inhibitor 8297		73.0 mM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Disruption of the blood brain barrier and abnormal vascularity in brain, spine and associated tissues 22 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdf	Diagnostic	Approved 8429	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
Central nervous system diseases 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8429	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
Breast cancer 434 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8429	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
Renal artery obstruction 22 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8429	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

Title	Date	PubMed
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.	1997 May	9109525
Aluminum is a weak agonist for the calcium-sensing receptor.	1999 May	10231437
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	11179201
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow.	2001 Feb 9	11071898
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	11988098
Gadolinium-containing contrast media for radiographic examinations: a position paper.	2002 Oct	12271402
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium.	2004 May	15068510
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.	2005 Apr 20	15843607
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.	2006 Apr 28	16522635
Renal safety of gadolinium-based contrast agent for ionizing radiation imaging.	2006 Jul	16793989
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.	2015 Mar	25249313
MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T.	2016 Mar	26123410

Patents

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

GADOXETATE DISODIUM

Official Name

English

ZK-139834

Code

English

ZK 139834

Code

English

DISODIUM (N-((2S)-2-(BIS(CARBOXYMETHYL)AMINO)-3-(P-ETHOXYPHENYL)PROPYL)-N-(2-(BIS(CARBOXYMETHYL)AMINO)ETHYL)GLYCINATO(5-))GADOLINATE(2-)

Common Name

English

SODIUM GADOXETATE [MART.]

Common Name

English

GADOXETATE DISODIUM [VANDF]

Common Name

English

GADOXETATE DISODIUM [ORANGE BOOK]

Common Name

English

GADOXETIC ACID DISODIUM

Common Name

English

SHL-569B

Code

English

EOVIST

Brand Name

English

GADOXETATE DISODIUM [USAN]

Common Name

English

Gadoxetate disodium [WHO-DD]

Common Name

English

GADOXETIC ACID SODIUM SALT [MI]

Common Name

English

GADOXETATE SODIUM [JAN]

Common Name

English

GADOXETATE SODIUM

Common Name

English

GADOLINATE(2-), (N-(2-(BIS((CARBOXY-.KAPPA.O)METHYL)AMINO-.KAPPA.N)-3-(4-ETHOXYPHENYL)PROPYL)-N-(2-(BIS((CARBOXY-.KAPPA.O)METHYL)AMINO-.KAPPA.N)ETHYL)GLYCINATO(5-)-.KAPPA.N,.KAPPA.O)-, DISODIUM, (SA-8-11252634-(S))-

Common Name

English

GADOXETIC ACID, DISODIUM

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C62358