Gadofosveset trisodium

Identification

Summary

Gadofosveset trisodium is an intravenous contrast agent used during magnetic resonance angiography (MRA) to evaluate aortoiliac occlusive disease (AIOD) in adults with peripheral vascular disease.

Brand Names

Vasovist

Generic Name

Gadofosveset trisodium

DrugBank Accession Number

DB06705

Background

Gadofosveset trisodium is an intravenous contrast agent used with magnetic resonance angiography(MRA), which is a non-invasive way of imaging blood vessels. The agent allows for the vascular system to be imaged more clearly by the MRA. In this way, gadofosveset trisodium is used to help diagnose certain disorders of the heart and blood vessels.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 1003.85
Monoisotopic: 1004.081
Chemical Formula: C₃₃H₃₈GdN₃Na₅O₁₄P

Synonyms

Gadofosveset

External IDs

MS-325

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Pharmacology

Indication

Gadofosveset trisodium is indicated for use as a contrast agent in magnetic resonance angiography (MRA) to evaluate aortoiliac occlusive disease (AIOD) in adults with known or suspected peripheral vascular disease.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Diagnostic agent	Aortoiliac occlusive disease		••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Gadofosveset causes signal enhancement by shortening the T1 of water molecules that interact with it. The contrast agent complex's rotation rate is the primary factor determining the magnitude of relaxation enhancement. This relaxation enhancement increase only occurs when bound to human serum albumin.

Mechanism of action

Gadofosveset binds reversibly to endogenous serum albumin resulting in longer vascular residence time than non-protein binding contrast agents. The binding to serum albumin also increases the magnetic resonance relaxivity of gadofosveset and decreases the relaxation time (Tl) of water protons resulting in an increase in signal intensity (brightness) of blood.

Absorption

Not Available

Volume of distribution

48 ± 16 mL/kg

Protein binding

80-90%

Metabolism

Gadofosveset does not undergo measurable metabolism.

Route of elimination

Gadofosveset is eliminated primarily in the urine with approximately 83.5% of an injected dose excreted in the urine over 14 days. Ninety-four percent (94%) of urinary excretion occurs in the first 72 hours. A small portion of gadofosveset dose is recovered in feces (approximately 4.7%).

Half-life

18.5 hours

Clearance

6.57 ± 0.97 mL/h/kg following the administration of 0.03 mmol/kg.

Adverse Effects

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Toxicity

Gadolinium-based contrast agents increase the risk for nephrogenic systemic fibrosis (NSF) in patients with acute or chronic severe renal insufficiency (glomerular filtration rate < 30 mL/min/1.73m²).

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
Abacavir	Abacavir may decrease the excretion rate of Gadofosveset trisodium which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Gadofosveset trisodium which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Gadofosveset trisodium which could result in a higher serum level.
Acetaminophen	Acetaminophen may decrease the excretion rate of Gadofosveset trisodium which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Gadofosveset trisodium which could result in a lower serum level and potentially a reduction in efficacy.

Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Gadofosveset trisodium monohydrate	XM33Q67UVH	211570-55-7	PIZALBORPSCYJU-QSQMUHTISA-H

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Gadolinium cation (3+)	ionic	AZV954TZ9N	22541-19-1	RJOJUSXNYCILHH-UHFFFAOYSA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ablavar	Injection, solution	0.25 mmol/ml	Intravenous	Tmc Pharma Services Ltd.	2016-09-20	2011-11-14
Ablavar	Injection, solution	0.25 mmol/ml	Intravenous	Tmc Pharma Services Ltd.	2016-09-20	2011-11-14
Ablavar	Injection, solution	0.25 mmol/ml	Intravenous	Tmc Pharma Services Ltd.	2016-09-20	2011-11-14
Ablavar	Injection, solution	0.25 mmol/ml	Intravenous	Tmc Pharma Services Ltd.	2016-09-20	2011-11-14
Ablavar	Injection, solution	0.25 mmol/ml	Intravenous	Tmc Pharma Services Ltd.	2016-09-20	2011-11-14

Chemical Identifiers

UNII: 9430ZR8ZAN
CAS number: 193901-90-5
InChI Key: XGOSYNSWSRUASG-SSMZTGFVSA-H
InChI: 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
IUPAC Name
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)(C1=CC=CC=C1)C1=CC=CC=C1)N(CC([O-])=O)CC([O-])=O

References

General References

Raman FS, Nacif MS, Cater G, Gai N, Jones J, Li D, Sibley CT, Liu S, Bluemke DA: 3.0-T whole-heart coronary magnetic resonance angiography: comparison of gadobenate dimeglumine and gadofosveset trisodium. Int J Cardiovasc Imaging. 2013 Jun;29(5):1085-94. doi: 10.1007/s10554-013-0192-z. Epub 2013 Mar 21. [Article]
Hrdina L, Kocher M, Herman M, Cerna M, Kozak J, Tudos Z, Mahathmakanthi S, Langova K: Comparison of the quality of lower limb magnetic resonance angiographies performed with different paramagnetic contrast agents in relation to body mass index and ejection fraction. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2012 Jun;156(2):164-70. doi: 10.5507/bp.2011.058. [Article]
Thouet T, Schnackenburg B, Kokocinski T, Fleck E, Nagel E, Kelle S: Visualization of chronic myocardial infarction using the intravascular contrast agent MS-325 (gadofosveset) in patients. ScientificWorldJournal. 2012;2012:236401. doi: 10.1100/2012/236401. Epub 2012 Mar 12. [Article]
Milot L, Haider M, Foster L, McGregor C, Law C: Gadofosveset trisodium in the investigation of focal liver lesions in noncirrhotic liver: Early experience. J Magn Reson Imaging. 2012 Sep;36(3):738-42. doi: 10.1002/jmri.23650. Epub 2012 Apr 5. [Article]
Caravan P: Protein-targeted gadolinium-based magnetic resonance imaging (MRI) contrast agents: design and mechanism of action. Acc Chem Res. 2009 Jul 21;42(7):851-62. doi: 10.1021/ar800220p. [Article]
FDA Approved Drug Products: ABLAVAR (gadofosveset trisodium) injection [Link]

External Links

KEGG Drug: D04286
PubChem Compound: 73049652
PubChem Substance: 175427086
ChemSpider: 9847191
RxNav: 1364289
ChEMBL: CHEMBL1908362
PharmGKB: PA165958378
Drugs.com: Drugs.com Drug Page
Wikipedia: Gadofosveset

FDA label

Download (148 KB)

MSDS

Download (66.5 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Diagnostic	Chronic Liver Disease	1
4	Completed	Other	Pediatric Congenital Heart Disease	1
4	Unknown Status	Diagnostic	Congenital Heart Disease (CHD)	1
4	Withdrawn	Diagnostic	Ovarian Neoplasms	1
3	Completed	Diagnostic	Peripheral Vascular Disease Patient	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, solution	Intravenous	0.25 mmol/ml
Injection, solution	Intravenous	244 mg/1mL
Injection	Intravenous	244 mg/1mL
Injection, solution	Intravenous
Solution	Intravenous	244 mg / mL

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
CA2304461	No	2008-10-14	2018-08-17
CA2211100	No	2007-03-20	2016-01-16
US6676929	No	2004-01-13	2020-05-04

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.169 mg/mL	ALOGPS
logP	3.84	ALOGPS
logS	-3.8	ALOGPS
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.8572
Blood Brain Barrier	+	0.6355
Caco-2 permeable	-	0.5948
P-glycoprotein substrate	Substrate	0.6107
P-glycoprotein inhibitor I	Inhibitor	0.6422
P-glycoprotein inhibitor II	Non-inhibitor	0.6901
Renal organic cation transporter	Non-inhibitor	0.6739
CYP450 2C9 substrate	Non-substrate	0.7903
CYP450 2D6 substrate	Non-substrate	0.8158
CYP450 3A4 substrate	Non-substrate	0.5501
CYP450 1A2 substrate	Non-inhibitor	0.7768
CYP450 2C9 inhibitor	Non-inhibitor	0.7121
CYP450 2D6 inhibitor	Non-inhibitor	0.8278
CYP450 2C19 inhibitor	Non-inhibitor	0.6916
CYP450 3A4 inhibitor	Non-inhibitor	0.7875
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8798
Ames test	Non AMES toxic	0.6081
Carcinogenicity	Non-carcinogens	0.7542
Biodegradation	Not ready biodegradable	0.9604
Rat acute toxicity	2.6392 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.5557
hERG inhibition (predictor II)	Non-inhibitor	0.5302

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available
Chromatographic Properties: Collision Cross Sections (CCS)
Not Available

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Meaney JF, Goyen M: Recent advances in contrast-enhanced magnetic resonance angiography. Eur Radiol. 2007 Mar;17 Suppl 2:B2-6. [Article]
Caravan P: Protein-targeted gadolinium-based magnetic resonance imaging (MRI) contrast agents: design and mechanism of action. Acc Chem Res. 2009 Jul 21;42(7):851-62. doi: 10.1021/ar800220p. [Article]
Caravan P, Parigi G, Chasse JM, Cloutier NJ, Ellison JJ, Lauffer RB, Luchinat C, McDermid SA, Spiller M, McMurry TJ: Albumin binding, relaxivity, and water exchange kinetics of the diastereoisomers of MS-325, a gadolinium(III)-based magnetic resonance angiography contrast agent. Inorg Chem. 2007 Aug 6;46(16):6632-9. Epub 2007 Jul 11. [Article]
Henness S, Keating GM: Gadofosveset. Drugs. 2006;66(6):851-7. [Article]

Drug created at May 16, 2010 00:37 / Updated at September 09, 2021 09:05

Gadofosveset trisodium

Identification

Structure for Gadofosveset trisodium (DB06705)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Carriers

References