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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H38N3O14P.Gd.3Na
Molecular Weight 957.86
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GADOFOSVESET TRISODIUM ANHYDROUS

SMILES

[Na+].[Na+].[Na+].[Gd+3].[O-]C(=O)CN(CCN(CC([O-])=O)CC([O-])=O)C[C@H](COP([O-])(=O)OC1CCC(CC1)(C2=CC=CC=C2)C3=CC=CC=C3)N(CC([O-])=O)CC([O-])=O

InChI

InChIKey=XGOSYNSWSRUASG-SSMZTGFVSA-H
InChI=1S/C33H44N3O14P.Gd.3Na/c37-28(38)18-34(15-16-35(19-29(39)40)20-30(41)42)17-26(36(21-31(43)44)22-32(45)46)23-49-51(47,48)50-27-11-13-33(14-12-27,24-7-3-1-4-8-24)25-9-5-2-6-10-25;;;;/h1-10,26-27H,11-23H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48);;;;/q;+3;3*+1/p-6/t26-;;;;/m1..../s1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
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 C33H38N3O14P
Molecular Weight 731.6403
Charge -6
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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/

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

CNS Non-penetrant
1014
Curator's Comment: Gadoterate does not cross the intact blood-brain barrier and, therefore, does not enhance normal brain or lesions that have a normal blood-brain barrier, e.g. cysts, mature post-operative scars. However, disruption of the bloodbrain barrier or abnormal vascularity allows distribution of gadoterate in lesions such as neoplasms, abscesses, and infarcts.

Originator

Approval Year

1988
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Serum paraoxonase/arylesterase 1
31
Target ID: P27169
Gene ID: 5444.0
Gene Symbol: PON1
Target Organism: Homo sapiens (Human)
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)
Inhibitor
8297
 73.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
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
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

PubMed

TitleDatePubMed
Aluminum is a weak agonist for the calcium-sensing receptor.
1999 May
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
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium.
2004 May
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.
2006 Apr 28
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 agents and nephrotoxicity.
2006 Nov
Gadolinium and kidney disease: are your patients at risk?
2008 Mar-Apr
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
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity.
2010 Aug
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
Non-clinical safety assessment of gadoterate meglumine (Dotarem(®)) in neonatal and juvenile rats.
2015 Dec
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.
2015 Mar
Patents

Patents

08147802
22
EP0454078A2
22
EP0835140B1
22
EP2698169A1
22
US20130052141
22
US5886158
22
US5980864
22
US8192721
22
US8901294
22
WO2014114664A1
22

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 16:02:48 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:48 GMT 2023
Record UNII
9430ZR8ZAN
Record Status Validated (UNII)
Record Version
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Name Type Language
GADOFOSVESET TRISODIUM ANHYDROUS
Common Name English
TRISODIUM (N-(2-(BIS(CARBOXYMETHYL)AMINO)ETHYL)-N-((R)-2-(BIS(CARBOXYMETHYL)AMINO)-3-HYDROXYPROPYL)GLYCINE 4,4-DIPHENYLCYCLOHEXYL HYDROGEN PHOSPHATO(6-)) GADOLINATE(3-)
Common Name English
GADOFOSVESET TRISODIUM SALT
MI  
Common Name English
GADOFOSVESET TRISODIUM SALT [MI]
Common Name English
TRISODIUM (N-(2-(BIS(CARBOXYMETHYL)AMINO)ETHYL)-N-((R)-2-(BIS(CARBOXYMETHYL)AMINO)-3-HYDROXYPROPYL)GLYCINE 4,4-DIPHENYLCYCLOHEXYL HYDROGEN PHOSPHATO (6-))GADOLINATE(3-)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C62358
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
Code System Code Type Description
CAS
193901-90-5
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
MERCK INDEX
m5625
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40941084
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
DRUG BANK
DB06705
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
FDA UNII
9430ZR8ZAN
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
PUBCHEM
11672461
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
HSDB
8232
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
NCI_THESAURUS
C81058
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
Related Record Type Details
Structure of GADOLINIUM CATION (3+)
PARENT -> SALT/SOLVATE
Structure of GADOFOSVESET TRISODIUM
SOLVATE->ANHYDROUS
Structure of FOSVESET
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of GADOLINIUM CATION (3+)
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