GADOPENTETIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H18N3O10.Gd.2H
Molecular Weight	547.57
Optical Activity	NONE
Defined Stereocenters	0 / 0
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)CC([O-])=O

InChI

InChIKey=IZOOGPBRAOKZFK-UHFFFAOYSA-K

InChI=1S/C14H23N3O10.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;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);/q;+3/p-3

HIDE SMILES / InChI

Molecular Formula	C14H20N3O10
Molecular Weight	390.3227
Charge	-3
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry
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
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 8504		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 8504		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 8583	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 8583	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 432 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8583	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 8583	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
MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T.	2016-03	26123410
Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats.	2015-12	26382613
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).	2015-09	26185325
MR Angiography at 3 T of Peripheral Arterial Disease: A Randomized Prospective Comparison of Gadoterate Meglumine and Gadobutrol.	2015-06	26001243
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.	2015-03	25249313
Tumor Detection at 3 Tesla with an Activatable Cell Penetrating Peptide Dendrimer (ACPPD-Gd), a T1 Magnetic Resonance (MR) Molecular Imaging Agent.	2015	26336058
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.	2013-04	23435930
Toxicological safety evaluation of gadobutrol.	2012-11	23011188
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.	2011-02-18	21127073
Heavy metal cations permeate the TRPV6 epithelial cation channel.	2011-01	21146870
Persistent activation of dermal fibroblasts from patients with gadolinium-associated nephrogenic systemic fibrosis.	2010-11	20570839
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity.	2010-08	20398695
Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture.	2010-03	20064552
Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency.	2009-12	19909415
Release of ATP from rat urinary bladder mucosa: role of acid, vanilloids and stretch.	2009-12	19860742
Large sample of nephrogenic systemic fibrosis cases from a single institution.	2009-10	19841395
Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry.	2008-11-01	18821778
Renal failure and gadolinium. The number of documented cases is rising.	2008-10	19537311
Quantification of gadolinium in nephrogenic systemic fibrosis: re-examination of a reported cohort with analysis of clinical factors.	2008-08	18538448
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.	2008-07	18316702
Gadolinium and kidney disease: are your patients at risk?	2008-05-14	18472687
Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue.	2008-04	18356456
Suggesting gadolinium-based contrast media for CT in azotemic patients is not based on historical, clinical, and experimental data.	2007-08	17641384
Gadolinium contrast may be risky in kidney disease.	2007-06-30	17599982
Gadolinium-based contrast agents and nephrotoxicity.	2006-11	17039541
Renal safety of gadolinium-based contrast agent for ionizing radiation imaging.	2006-07	16793989
Loss of primary cilia results in deregulated and unabated apical calcium entry in ARPKD collecting duct cells.	2006-06	16396941
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.	2006-04-28	16522635
Gadolinium-based contrast media for multi-detector row spiral CT pulmonary angiography in patients with renal insufficiency.	2006-03	16505405
Gadolinium-based contrast agents and nephrotoxicity in patients undergoing coronary artery procedures.	2006-02	16400668
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.	2005-04-20	15843607
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium.	2004-05	15068510
Gadolinium-containing contrast media for radiographic examinations: a position paper.	2002-10	12271402
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations.	2002-06-01	12163980
Diacylglycerol activates the influx of extracellular cations in T-lymphocytes independently of intracellular calcium-store depletion and possibly involving endogenous TRP6 gene products.	2002-05-15	11988098
The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel.	2001-02-16	11179201
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow.	2001-02-09	11071898
Aluminum is a weak agonist for the calcium-sensing receptor.	1999-05	10231437
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.	1997-05	9109525
Aluminum-induced DNA synthesis in osteoblasts: mediation by a G-protein coupled cation sensing mechanism.	1994-09	7806584

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 `Mon Mar 31 18:21:50 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:50 GMT 2025`
Record UNII	K2I13DR72L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GADOPENTETIC ACID

Official Name

English

GADODIAMIDE HYDRATE IMPURITY B [EP IMPURITY]

Preferred Name

English

GADOPENTETIC ACID [MI]

Common Name

English

gadopentetic acid [INN]

Common Name

English

GADOPENTETIC ACID [MART.]

Common Name

English

Gadopentetic acid [WHO-DD]

Common Name

English

MEGLUMINE GADOPENTETATE [JAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QV08CA01