GADOVERSETAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H34N5O10.Gd
Molecular Weight	661.76
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Gd+3].COCCNC(=O)CN(CCN(CCN(CC([O-])=O)CC(=O)NCCOC)CC([O-])=O)CC([O-])=O

InChI

InChIKey=HBEAOBRDTOXWRZ-UHFFFAOYSA-K

InChI=1S/C20H37N5O10.Gd/c1-34-9-3-21-16(26)11-24(14-19(30)31)7-5-23(13-18(28)29)6-8-25(15-20(32)33)12-17(27)22-4-10-35-2;/h3-15H2,1-2H3,(H,21,26)(H,22,27)(H,28,29)(H,30,31)(H,32,33);/q;+3/p-3

HIDE SMILES / InChI

Molecular Formula	C20H34N5O10
Molecular Weight	504.5115
Charge	-3
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

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
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
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations.	2002 Jun 1	12163980
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
Gadolinium-based contrast agents and nephrotoxicity in patients undergoing coronary artery procedures.	2006 Feb	16400668
Renal safety of gadolinium-based contrast agent for ionizing radiation imaging.	2006 Jul	16793989
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-based contrast agents and nephrotoxicity.	2006 Nov	17039541
Suggesting gadolinium-based contrast media for CT in azotemic patients is not based on historical, clinical, and experimental data.	2007 Aug	17641384
Gadolinium contrast may be risky in kidney disease.	2007 Jun 30	17599982
Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue.	2008 Apr	18356456
Quantification of gadolinium in nephrogenic systemic fibrosis: re-examination of a reported cohort with analysis of clinical factors.	2008 Aug	18538448
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.	2008 Jul	18316702
Gadolinium and kidney disease: are your patients at risk?	2008 Mar-Apr	18472687
Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry.	2008 Nov 1	18821778
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
Large sample of nephrogenic systemic fibrosis cases from a single institution.	2009 Oct	19841395
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
Toxicological safety evaluation of gadobutrol.	2012 Nov	23011188
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.	2013 Apr	23435930
Tumor Detection at 3 Tesla with an Activatable Cell Penetrating Peptide Dendrimer (ACPPD-Gd), a T1 Magnetic Resonance (MR) Molecular Imaging Agent.	2015	26336058
Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats.	2015 Dec	26382613
MR Angiography at 3 T of Peripheral Arterial Disease: A Randomized Prospective Comparison of Gadoterate Meglumine and Gadobutrol.	2015 Jun	26001243
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.	2015 Mar	25249313
The Benefits of High Relaxivity for Brain Tumor Imaging: Results of a Multicenter Intraindividual Crossover Comparison of Gadobenate Dimeglumine with Gadoterate Meglumine (The BENEFIT Study).	2015 Sep	26185325
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:55:10 GMT 2023` Edited by `admin` on `Fri Dec 15 15:55:10 GMT 2023`
Record UNII	RLM74T3Z9D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GADOVERSETAMIDE

Official Name

English

MP-1177

Code

English

GADOVERSETAMIDE [USP-RS]

Common Name

English

GADOVERSETAMIDE [USP IMPURITY]

Common Name

English

OPTIMARK

Brand Name

English

GADOVERSETAMIDE [USAN]

Common Name

English

GADOVERSETAMIDE [MI]

Common Name

English

GADOVERSETAMIDE [JAN]

Common Name

English

[N,N-Bis[2-[(carboxymethyl)[[(2-methoxyethyl)carbamoyl]methyl]amino]ethyl]glycinato(3-)]gadolinium

Common Name

English

Gadoversetamide [WHO-DD]

Common Name

English

GADOVERSETAMIDE [VANDF]

Common Name

English

GADOVERSETAMIDE [MART.]

Common Name

English

GADOVERSETAMIDE [USP MONOGRAPH]

Common Name

English

GADOVERSETAMIDE [EMA EPAR]

Common Name

English

GADOVERSETAMIDE [HSDB]

Common Name

English

(8,11-BIS(CARBOXYMETHYL)-14-(2-((2-METHOXYETHYL)AMINO)-2-OXOETHYL)-6-OXO-2-OXA-5,8,11,14-TETRAAZAHEXADECAN-16-OATO(3-)), GADOLINIUM

Common Name

English

GADOVERSETAMIDE [ORANGE BOOK]

Common Name

English

gadoversetamide [INN]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

OPTIMARK (AUTHORIZED: MAGNETIC RESONANCE IMAGING)