GADOFOSVESET TRISODIUM

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201277s000lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serum paraoxonase/arylesterase 1 31 Target ID: P27169 Gene ID: 5444.0 Gene Symbol: PON1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/31179770	Inhibitor 8228		105.0 mM [Ki]
6-phosphogluconate dehydrogenase, decarboxylating 29 Target ID: P52209 Gene ID: 5226.0 Gene Symbol: PGD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20235752	Inhibitor 8228		73.0 mM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Disruption of the blood brain barrier and abnormal vascularity in brain, spine and associated tissues 22 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204781s000lbl.pdf	Diagnostic	Approved 8360	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
Central nervous system diseases 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8360	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
Breast cancer 431 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8360	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
Renal artery obstruction 22 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201277s011lbl.pdf	Diagnostic	Approved 8360	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

Title	Date	PubMed

Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.	1997 May	9109525
Inhibition of transiently expressed low- and high-voltage-activated calcium channels by trivalent metal cations.	2002 Jun 1	12163980
Gadolinium-containing contrast media for radiographic examinations: a position paper.	2002 Oct	12271402
A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium.	2004 May	15068510
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.	2005 Apr 20	15843607
Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.	2006 Apr 28	16522635
Renal safety of gadolinium-based contrast agent for ionizing radiation imaging.	2006 Jul	16793989
Gadolinium-based contrast agents and nephrotoxicity.	2006 Nov	17039541
Gadolinium and kidney disease: are your patients at risk?	2008 Mar-Apr	18472687
Use of gadolinium for carotid artery angiography and stenting in patients with renal insufficiency.	2009 Dec	19909415
Release of ATP from rat urinary bladder mucosa: role of acid, vanilloids and stretch.	2009 Dec	19860742
Large sample of nephrogenic systemic fibrosis cases from a single institution.	2009 Oct	19841395
Impaired mitochondrial function and oxidative stress in rat cortical neurons: implications for gadolinium-induced neurotoxicity.	2010 Aug	20398695
Differential expression of TRPM2 and TRPV4 channels and their potential role in oxidative stress-induced cell death in organotypic hippocampal culture.	2010 Mar	20064552
Toxicological safety evaluation of gadobutrol.	2012 Nov	23011188
MR Angiography at 3 T of Peripheral Arterial Disease: A Randomized Prospective Comparison of Gadoterate Meglumine and Gadobutrol.	2015 Jun	26001243
Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging.	2015 Mar	25249313
MRI in multiple sclerosis: an intra-individual, randomized and multicentric comparison of gadobutrol with gadoterate meglumine at 3 T.	2016 Mar	26123410

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

GADOFOSVESET TRISODIUM

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)