GADOBENIC ACID

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H26N3O11.Gd.2H
Molecular Weight	667.72
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H+].[H+].[Gd+3].[O-]C(=O)CN(CCN(CC([O-])=O)CC([O-])=O)CCN(CC([O-])=O)C(COCC1=CC=CC=C1)C([O-])=O

InChI

InChIKey=MXZROTBGJUUXID-UHFFFAOYSA-K

InChI=1S/C22H31N3O11.Gd/c26-18(27)10-23(6-7-24(11-19(28)29)12-20(30)31)8-9-25(13-21(32)33)17(22(34)35)15-36-14-16-4-2-1-3-5-16;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);/q;+3/p-3

HIDE SMILES / InChI

Molecular Formula	H
Molecular Weight	1.0079
Charge	1
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

Molecular Formula	C22H26N3O11
Molecular Weight	508.4553
Charge	-5
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 1.36373758E12
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 1.30006083E12
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 1.30006083E12
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 1.30006083E12

PubMed

Title	Date	PubMed
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
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
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
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
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
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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:32:47 UTC 2023` Edited by `admin` on `Fri Dec 15 16:32:47 UTC 2023`
Record UNII	15G12L5X8K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GADOBENIC ACID

Official Name

English

GADOBENATE

Common Name

English

gadobenic acid [INN]

Common Name

English

Gadobenic acid [WHO-DD]

Common Name

English

GADOLINATE(2-), (10-(CARBOXY-.KAPPA.O)-3,6,9-TRIS((CARBOXY-.KAPPA.O)METHYL)-13-PHENYL-12-OXA-3,6,9-TRIAZATRIDECANOATO(5-)-.KAPPA.N3,.KAPPA.N6,.KAPPA.N9,.KAPPA.O)-, HYDROGEN (1:2)

Systematic Name

English

2-OXA-5,8,11-TRIAZATRIDECAN-13-OIC ACID, 4-CARBOXY-5,8,11-TRIS(CARBOXYMETHYL)-1-PHENYL-, GADOLINIUM COMPLEX

Common Name

English

GADOLINATE(2-), (4-CARBOXY-5,8,11-TRIS(CARBOXYMETHYL)-1-PHENYL-2-OXA-5,8,11-TRIAZATRIDECAN-13-OATO(5-)-N5,N8,N11,O4,O5,O8,O11,O13)-, DIHYDROGEN

Common Name

English

GADOBENATE [VANDF]

Common Name

English

B-19036

Code

English

Classification Tree Code System Code

WHO-VATC

QV08CA08