GADOTERATE MEGLUMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H25N4O8.C7H17NO5.Gd
Molecular Weight	753.86
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1

InChI

InChIKey=RYHQMKVRYNEBNJ-BMWGJIJESA-K

InChI=1S/C16H28N4O8.C7H17NO5.Gd/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;1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28);4-13H,2-3H2,1H3;/q;;+3/p-3/t;4-,5+,6+,7+;/m.0./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
Aluminum-induced DNA synthesis in osteoblasts: mediation by a G-protein coupled cation sensing mechanism.	1994 Sep	7806584
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow.	2001 Feb 9	11071898
Loss of primary cilia results in deregulated and unabated apical calcium entry in ARPKD collecting duct cells.	2006 Jun	16396941
Gadolinium-based contrast media for multi-detector row spiral CT pulmonary angiography in patients with renal insufficiency.	2006 Mar	16505405
Gadolinium contrast may be risky in kidney disease.	2007 Jun 30	17599982
Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry.	2008 Nov 1	18821778
Release of ATP from rat urinary bladder mucosa: role of acid, vanilloids and stretch.	2009 Dec	19860742
Heavy metal cations permeate the TRPV6 epithelial cation channel.	2011 Jan	21146870
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.	2015 Mar	25249313

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

GADOTERATE MEGLUMINE

Official Name

English

GADOTERATE MEGLUMINE [USAN]

Common Name

English

GADOTERATE MEGLUMINE [USP-RS]

Common Name

English

P 449

Code

English

MEGLUMINE GADOTERATE [JAN]

Common Name

English

GADOLINIUM-DOTA MEGLUMINE

Common Name

English

GADOTERATE MEGLUMINE [VANDF]

Common Name

English

P-449

Code

English

GADOTERATE MEGLUMINE [ORANGE BOOK]

Common Name

English

GD-DOTA MEGLUMINE

Common Name

English

P449

Code

English

D-GLUCITOL, 1-DEOXY-1-(METHYLAMINO)-, (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)GADOLINATE(1-) (1:1)

Common Name

English

MEGLUMINE GADOTERATE

Common Name

English

DOTAREM

Brand Name

English

Meglumine gadoterate [WHO-DD]

Common Name

English

MAGNESCOPE

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C62358