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

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H38N3O14P.Gd.3Na.H2O
Molecular Weight 975.87
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GADOFOSVESET TRISODIUM

SMILES

O.[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=PIZALBORPSCYJU-QSQMUHTISA-H
InChI=1S/C33H44N3O14P.Gd.3Na.H2O/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);;;;;1H2/q;+3;3*+1;/p-6/t26-;;;;;/m1...../s1

HIDE SMILES / InChI

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 C33H39N3O14P
Molecular Weight 732.6482
Charge -5
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/

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
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.
1997 May
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations.
2002 Jun 1
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
Renal safety of gadolinium-based contrast agent for ionizing radiation imaging.
2006 Jul
Gadolinium-based contrast agents and nephrotoxicity.
2006 Nov
Gadolinium and kidney disease: are your patients at risk?
2008 Mar-Apr
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
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
Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture.
2010 Mar
Toxicological safety evaluation of gadobutrol.
2012 Nov
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

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 23:19:43 UTC 2023
Edited
by admin
on Wed Jul 05 23:19:43 UTC 2023
Record UNII
XM33Q67UVH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GADOFOSVESET TRISODIUM
DASH   EMA EPAR   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
GADOFOSVESET TRISODIUM [EMA EPAR]
Common Name English
GADOFOSVESET TRISODIUM MONOHYDRATE
Common Name English
VASOVIST
Brand Name English
Gadofosveset trisodium [WHO-DD]
Common Name English
GADOFOSVESET TRISODIUM [USAN]
Common Name English
ABLAVAR
Brand Name English
MS 32520
Code English
GADOFOSVESET TRISODIUM [MART.]
Common Name English
GADOFOSVESET TRISODIUM [VANDF]
Common Name English
TRISODIUM-((2-(R)-((4,4-DIPHENYLCYCLOHEXYL) PHOSPHONOOXYMETHYL)-DIETHYLENETRIAMINEPENTAACETATO)(AQUO) GADOLINIUM(III)
Common Name English
GADOFOSVESET TRISODIUM [ORANGE BOOK]
Common Name English
MS-32520
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS ABLAVAR (WITHDRAWN: RADIO RESONANCE PERFUSION)
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
NCI_THESAURUS C62358
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
Code System Code Type Description
FDA UNII
XM33Q67UVH
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
SMS_ID
100000089561
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
WIKIPEDIA
Gadofosveset
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
DAILYMED
XM33Q67UVH
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
DRUG BANK
DB06705
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
USAN
SS-17
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
RXCUI
1364289
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1908843
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
EVMPD
SUB21051
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
PUBCHEM
158440
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
NCI_THESAURUS
C81057
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
CAS
211570-55-7
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID501027793
Created by admin on Wed Jul 05 23:19:43 UTC 2023 , Edited by admin on Wed Jul 05 23:19:43 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY