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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H25N4O8.C7H17NO5.Gd
Molecular Weight 753.86
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GADOTERATE MEGLUMINE

SMILES

[Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1

InChI

InChIKey=RYHQMKVRYNEBNJ-BMWGJIJESA-K
InChI=1S/C16H28N4O8.C7H17NO5.Gd/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26;1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28);4-13H,2-3H2,1H3;/q;;+3/p-3/t;4-,5+,6+,7+;/m.0./s1

HIDE SMILES / InChI
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 C7H14NO5
Molecular Weight 192.1898
Charge -3
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C16H28N4O8
Molecular Weight 404.4155
Charge 0
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/

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

1.36373758E12
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
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
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

PubMed

TitleDatePubMed
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
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
Quantification of gadolinium in nephrogenic systemic fibrosis: re-examination of a reported cohort with analysis of clinical factors.
2008 Aug
Renal failure and gadolinium. The number of documented cases is rising.
2008 Oct
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
Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children.
2013 Apr
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
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 15:37:22 UTC 2023
Edited
by admin
on Fri Dec 15 15:37:22 UTC 2023
Record UNII
L0ND3981AG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GADOTERATE MEGLUMINE
DASH   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
GADOTERATE MEGLUMINE [USAN]
Common Name English
GADOTERATE MEGLUMINE [USP-RS]
Common Name English
P 449
Code English
MEGLUMINE GADOTERATE [JAN]
Common Name English
GADOLINIUM-DOTA MEGLUMINE
Common Name English
GADOTERATE MEGLUMINE [VANDF]
Common Name English
P-449
Code English
GADOTERATE MEGLUMINE [ORANGE BOOK]
Common Name English
GD-DOTA MEGLUMINE
Common Name English
P449
Code English
D-GLUCITOL, 1-DEOXY-1-(METHYLAMINO)-, (1,4,7,10-TETRAAZACYCLODODECANE-1,4,7,10-TETRAACETATO(4-)-.KAPPA.N1,.KAPPA.N4,.KAPPA.N7,.KAPPA.N10,.KAPPA.O1,.KAPPA.O4,.KAPPA.O7,.KAPPA.O10)GADOLINATE(1-) (1:1)
Common Name English
MEGLUMINE GADOTERATE
JAN   WHO-DD  
Common Name English
DOTAREM
Brand Name English
Meglumine gadoterate [WHO-DD]
Common Name English
MAGNESCOPE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C62358
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
Code System Code Type Description
USAN
ZZ-155
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
DRUG CENTRAL
1267
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
NCI_THESAURUS
C80124
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
RS_ITEM_NUM
1287620
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
HSDB
8230
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID80918856
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
RXCUI
1421151
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001229
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
EVMPD
SUB03121MIG
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
MESH
C072417
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
CAS
92943-93-6
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
PUBCHEM
6918037
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
SMS_ID
100000086167
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL2219415
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
CHEBI
73727
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
DAILYMED
L0ND3981AG
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
FDA UNII
L0ND3981AG
Created by admin on Fri Dec 15 15:37:22 UTC 2023 , Edited by admin on Fri Dec 15 15:37:22 UTC 2023
PRIMARY
Related Record Type Details
Structure of GADOLINIUM CATION (3+)
PARENT -> SALT/SOLVATE
Structure of MEGLUMINE
PARENT -> SALT/SOLVATE
Structure of TETRAXETAN
PARENT -> SALT/SOLVATE
Structure of GADOTERIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of GADOLINIUM CATION (3+)
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