GADOPENTETATE DIMEGLUMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H18N3O10.2C7H17NO5.Gd.2H
Molecular Weight	938.0
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LGMLJQFQKXPRGA-VPVMAENOSA-K

InChI=1S/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./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
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.	1997 May	9109525
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
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium.	2004 May	15068510
Gadolinium-based contrast agents and nephrotoxicity.	2006 Nov	17039541
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.	2008 Jul	18316702
Renal failure and gadolinium. The number of documented cases is rising.	2008 Oct	19537311
Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency.	2009 Dec	19909415
Release of ATP from rat urinary bladder mucosa: role of acid, vanilloids and stretch.	2009 Dec	19860742
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity.	2010 Aug	20398695
Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture.	2010 Mar	20064552
Persistent activation of dermal fibroblasts from patients with gadolinium-associated nephrogenic systemic fibrosis.	2010 Nov	20570839
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.	2011 Feb 18	21127073
Heavy metal cations permeate the TRPV6 epithelial cation channel.	2011 Jan	21146870
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.	2013 Apr	23435930
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

GADOPENTETATE DIMEGLUMINE

Official Name

English

SHL-451A

Code

English

GADOPENTETATE DIMEGLUMINE [VANDF]

Common Name

English

GADOPENTETATE DIMEGLUMINE [JAN]

Common Name

English

GADOPENTETATE DIMEGLUMINE [USAN]

Common Name

English

DIMEGLUMINE GADOPENTETATE

Common Name

English

GADOPENTETATE DIMEGLUMINE [ORANGE BOOK]

Common Name

English

SH L 451 A

Code

English

GADOPENTETATE DIMEGLUMINE [USP IMPURITY]

Common Name

English

DIHYDROGEN (N,N-BIS(2-(BIS(CARBOXYMETHYL)AMINO)ETHYL)GLYCINATO(5-))GADOLINATE(2-), COMPOUND WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:2)

Common Name

English

SH-L-451-A

Code

English

MEGLUMINE GADOPENTETATE [MART.]

Common Name

English

GADOPENTETATE DIMEGLUMINE [HSDB]

Common Name

English

Meglumine gadopentetate [WHO-DD]

Common Name

English

MAGNEVIST

Brand Name

English

GADOPENTETIC ACID DIMEGLUMINE SALT [MI]

Common Name

English

GADOPENTATE DIMEGLUMINE

Common Name

English

GADOLINATE(2-), (N,N-BIS(2-(BIS(CARBOXYMETHYL)AMINO)ETHYL)GLYCINATO(5-))-, DIHYDROGEN, COMPD. WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:2)

Common Name

English

MEGLUMINE GADOPENTETATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C62358