U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H38N3O14P.Gd.3H
Molecular Weight 891.91
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GADOFOSVESET

SMILES

[H+].[H+].[H+].[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=ZSDLYSDDELEVDD-UFTMZEDQSA-K
InChI=1S/C33H44N3O14P.Gd/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/p-3/t26-;/m1./s1

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 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

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.

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

2013
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

2011
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

2011
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

2011
PubMed

PubMed

TitleDatePubMed
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.
1997 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
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations.
2002 Jun 1
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.
2005 Apr 20
Gadolinium-based contrast agents and nephrotoxicity in patients undergoing coronary artery procedures.
2006 Feb
Large sample of nephrogenic systemic fibrosis cases from a single institution.
2009 Oct
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity.
2010 Aug
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
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

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 16:06:44 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:44 GMT 2023
Record UNII
E65RW73PHS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GADOFOSVESET
INN   MI   WHO-DD  
INN  
Official Name English
Gadofosveset [WHO-DD]
Common Name English
GADOFOSVESET [MI]
Common Name English
MS-325
Code English
D-GULONIC ACID
MI  
Common Name English
(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 [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C62358
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
WHO-VATC QV08CA11
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
WHO-ATC V08CA11
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
NDF-RT N0000175862
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
NDF-RT N0000180184
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
Code System Code Type Description
FDA UNII
E65RW73PHS
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
MERCK INDEX
m5625
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY Merck Index
MESH
C109932
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
NCI_THESAURUS
C81056
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
DAILYMED
E65RW73PHS
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
PUBCHEM
73415770
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID401027790
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
INN
8023
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
RXCUI
1364290
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY RxNorm
SMS_ID
100000089364
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
DRUG CENTRAL
3258
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908843
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
EVMPD
SUB25385
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
MERCK INDEX
m5881
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY Merck Index
CAS
201688-00-8
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
CHEBI
87753
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
LACTMED
Gadofosveset
Created by admin on Fri Dec 15 16:06:44 GMT 2023 , Edited by admin on Fri Dec 15 16:06:44 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
TARGET->LIGAND
Related Record Type Details
ACTIVE MOIETY