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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 of GADOPENTETIC ACID

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 C14H18N3O10
Molecular Weight 388.3068
Charge -5
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P27169
Gene ID: 5444.0
Gene Symbol: PON1
Target Organism: Homo sapiens (Human)
105.0 mM [Ki]
Target ID: P52209
Gene ID: 5226.0
Gene Symbol: PGD
Target Organism: Homo sapiens (Human)
73.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
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
Diagnostic
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
Diagnostic
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
Diagnostic
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

PubMed

TitleDatePubMed
Aluminum-induced DNA synthesis in osteoblasts: mediation by a G-protein coupled cation sensing mechanism.
1994 Sep
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.
1997 May
Aluminum is a weak agonist for the calcium-sensing receptor.
1999 May
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
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow.
2001 Feb 9
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations.
2002 Jun 1
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
Gadolinium-containing contrast media for radiographic examinations: a position paper.
2002 Oct
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium.
2004 May
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.
2005 Apr 20
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.
2006 Apr 28
Gadolinium-based contrast agents and nephrotoxicity in patients undergoing coronary artery procedures.
2006 Feb
Renal safety of gadolinium-based contrast agent for ionizing radiation imaging.
2006 Jul
Loss of primary cilia results in deregulated and unabated apical calcium entry in ARPKD collecting duct cells.
2006 Jun
Gadolinium-based contrast media for multi-detector row spiral CT pulmonary angiography in patients with renal insufficiency.
2006 Mar
Gadolinium-based contrast agents and nephrotoxicity.
2006 Nov
Suggesting gadolinium-based contrast media for CT in azotemic patients is not based on historical, clinical, and experimental data.
2007 Aug
Gadolinium contrast may be risky in kidney disease.
2007 Jun 30
Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue.
2008 Apr
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.
2008 Jul
Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry.
2008 Nov 1
Renal failure and gadolinium. The number of documented cases is rising.
2008 Oct
Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency.
2009 Dec
Release of ATP from rat urinary bladder mucosa: role of acid, vanilloids and stretch.
2009 Dec
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity.
2010 Aug
Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture.
2010 Mar
Persistent activation of dermal fibroblasts from patients with gadolinium-associated nephrogenic systemic fibrosis.
2010 Nov
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.
2011 Feb 18
Heavy metal cations permeate the TRPV6 epithelial cation channel.
2011 Jan
Toxicological safety evaluation of gadobutrol.
2012 Nov
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.
2013 Apr
Tumor Detection at 3 Tesla with an Activatable Cell Penetrating Peptide Dendrimer (ACPPD-Gd), a T1 Magnetic Resonance (MR) Molecular Imaging Agent.
2015
Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats.
2015 Dec
MR Angiography at 3 T of Peripheral Arterial Disease: A Randomized Prospective Comparison of Gadoterate Meglumine and Gadobutrol.
2015 Jun
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.
2015 Mar
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
MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T.
2016 Mar
Patents

Sample Use Guides

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 23:39:56 UTC 2023
Edited
by admin
on Wed Jul 05 23:39:56 UTC 2023
Record UNII
K2I13DR72L
Record Status Validated (UNII)
Record Version
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Name Type Language
GADOPENTETIC ACID
INN   MART.   MI   WHO-DD  
INN  
Official 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
GADODIAMIDE HYDRATE IMPURITY B [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QV08CA01
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
NDF-RT N0000180184
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
NCI_THESAURUS C62358
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
WHO-ATC V08CA01
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
NDF-RT N0000175862
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
Code System Code Type Description
WIKIPEDIA
GADOPENTETIC ACID
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
SMS_ID
100000085029
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
NCI_THESAURUS
C87737
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
MERCK INDEX
M5627
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00789
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
INN
5396
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200431
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
PUBCHEM
157429
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID701001301
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
CAS
80529-93-7
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
EVMPD
SUB07864MIG
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
FDA UNII
K2I13DR72L
Created by admin on Wed Jul 05 23:39:57 UTC 2023 , Edited by admin on Wed Jul 05 23:39:57 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY