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/2013/204781s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.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/

Gadobutrol is a second-generation extracellular non-ionic macrocyclic GBCA that is used in patients undergoing diagnostic contrast-enhanced MRI for visualization of pathological lesions in the CNS and all other body regions or for contrast-enhanced magnetic resonance angiography (MRA) to evaluate perfusion and flow-related abnormalities. It is a non-ionic, paramagnetic complex consisting of gadolinium (Gd3+) chelated with the macrocyclic compound dihydroxy-hydroxymethylpropyl-tetraazacyclododecane-triacetic acid (butrol). Gadavist (the trade name of gadobutrol) was approved by FDA in 2011 for intravenous use in diagnostic MRI in adults and children (2 years of age and older) to detect and visualize areas with disrupted blood brain barrier and/or abnormal vascularity of the central nervous system. Application of gadobutrol in humans, up to a dose of 0.5 mmol/kg was shown to be well tolerated. Following intravenous administration, gadobutrol may increase MRI sensitivity for the detection of tumors and inflammatory and demyelinating diseases of the central nervous system which are associated with areas with blood-brain barrier defects due to altered perfusion or an enlarged extracellular space. Gadobutrol is not metabolized. It is eliminated in an unchanged form via the kidneys; extra-renal elimination is negligible. Side effects include headache, nausea, abnormal taste and feeling hot.

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 8228		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 8228		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 8360	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 1.36373758E12
Central nervous system diseases 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8360	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 1.30006083E12
Breast cancer 431 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8360	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 1.30006083E12
Renal artery obstruction 22 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8360	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 1.30006083E12

PubMed

Title	Date	PubMed
Aluminum-induced DNA synthesis in osteoblasts: mediation by a G-protein coupled cation sensing mechanism.	1994 Sep	7806584
Aluminum is a weak agonist for the calcium-sensing receptor.	1999 May	10231437
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
Gadolinium-based contrast agents and nephrotoxicity in patients undergoing coronary artery procedures.	2006 Feb	16400668
Loss of primary cilia results in deregulated and unabated apical calcium entry in ARPKD collecting duct cells.	2006 Jun	16396941
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
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
Large sample of nephrogenic systemic fibrosis cases from a single institution.	2009 Oct	19841395
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
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.	2013 Apr	23435930
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

For adult and pediatric patients (2 years and older), the recommended dose of DOTAREM (gadoterate meglumine) is 0.2 mL/kg (0.1 mmol/kg) body weight administered as an intravenous bolus injection, manually or by power injector, at a flow rate of approximately 2 mL/second for adults and 1-2 mL/second for pediatric patients.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:23:32 UTC 2023` Edited by `admin` on `Wed Jul 05 23:23:32 UTC 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)