Flutemetamol (18F)

Identification

Summary

Flutemetamol (18F) is a radiopharmaceutical diagnostic agent used during Positron Emission Tomography (PET) imaging of the brain to estimate β-amyloid neuritic plaque density in adult patients to diagnose the causes of cognitive impairment.

Brand Names
Vizamyl
Generic Name
Flutemetamol (18F)
DrugBank Accession Number
DB09151
Background

Flutemetamol (18F) is a PET scanning radiopharmaceutical containing the radionuclide fluorine-18. It is indicated for Positron Emission Tomography (PET) imaging of the brain to estimate β amyloid neuritic plaque density in adult patients with cognitive impairment who are being evaluated for Alzheimer's disease (AD) or other causes of cognitive decline.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 273.32
Monoisotopic: 273.060146823
Chemical Formula
C14H11FN2OS
Synonyms
  • [18F]-Flutemetamol
  • 2-[3-(18F)fluoro-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol
  • Flutemetamol (18F)
  • Flutemetamol F 18
  • Flutemetamol F-18
  • Flutemetamol F18
External IDs
  • (18F)AH110690

Pharmacology

Indication

Flutemetamol F18 is indicated for Positron Emission Tomography (PET) imaging of the brain to estimate β amyloid neuritic plaque density in adult patients with cognitive impairment who are being evaluated for Alzheimer's disease (AD) or other causes of cognitive decline.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentAlzheimer's disease••••••••••••
Diagnostic agentCognitive decline••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Following intravenous injection, flutemetamol F 18 diffuses across the human blood-brain barrier and produces a radioactivity signal detectable throughout the brain. Subsequently, cerebral perfusion decreases the brain flutemetamol F 18 content, with differential retention of the drug in cortical areas that contain β-amyloid aggregates compared to areas that lack the aggregates.

Mechanism of action

Fluorine-18 (F 18) is a cyclotron-produced radionuclide that decays by positron emission (β+ decay, 96.7%) and orbital electron capture (3.3%) to stable oxygen-18 with a physical half-life of 109.8 minutes. The positron can undergo annihilation with an electron to produce two gamma rays; the energy of each gamma ray is 511 keV. After flumetamol F18 is given intravenously, it accumulates in beta amyloid plaques in the brain, and thus becomes visible via positron emission tomography (PET).

TargetActionsOrganism
AAmyloid beta A4 protein
binder
Humans
Absorption

The time-activity curves for flutemetamol F 18 in the brain of subjects with positive scans shows continual signal increases from time zero through 30 minutes post administration, with stable values thereafter up to at least 120 minutes post-injection. Following intravenous injection of 185 MBq (5 mCi) of Vizamyl in humans, flutemetamol F 18 plasma concentrations declined by approximately 75% in the first 20 minutes post-injection, and by approximately 90% in the first 180 minutes.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

The F 18 in circulation during the 30-120 minutes imaging window in plasma was principally associated with flutemetamol metabolites.

Route of elimination

Excretion was found to be approximately 37% renal and 52% hepatobiliary.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Most commonly reported adverse reactions were flushing (2%), headache (1%), increased blood pressure (2%), nausea (1%), and dizziness (1%).

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.
Not Available
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VizamylInjection, solution400 MBq/mLIntravenousGe Healthcare As2021-02-10Not applicableEU flag
VizamylSolution4.05 mCi/1mLIntravenousMedi-Physics, Inc. dba GE Healthcare2014-01-01Not applicableUS flag
VizamylInjection, solution400 MBq/mLIntravenousGe Healthcare As2021-02-10Not applicableEU flag

Categories

ATC Codes
V09AX04 — Flutemetamol (18f)
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazoles
Sub Class
Not Available
Direct Parent
Benzothiazoles
Alternative Parents
Phenylalkylamines / Aniline and substituted anilines / Secondary alkylarylamines / Fluorobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl fluorides / Thiazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
1,3-benzothiazole / 1-hydroxy-2-unsubstituted benzenoid / Amine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles, secondary amino compound, aromatic amine, ring assembly, fluorine-18 radiopharmaceutical (CHEBI:76611)
Affected organisms
Not Available

Chemical Identifiers

UNII
L49M066S0O
CAS number
765922-62-1
InChI Key
VVECGOCJFKTUAX-HUYCHCPVSA-N
InChI
InChI=1S/C14H11FN2OS/c1-16-11-4-2-8(6-10(11)15)14-17-12-5-3-9(18)7-13(12)19-14/h2-7,16,18H,1H3/i15-1
IUPAC Name
2-[3-(¹⁸F)fluoro-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol
SMILES
CNC1=C([18F])C=C(C=C1)C1=NC2=CC=C(O)C=C2S1

References

General References
  1. Beach TG, Thal DR, Zanette M, Smith A, Buckley C: Detection of Striatal Amyloid Plaques with [18F]flutemetamol: Validation with Postmortem Histopathology. J Alzheimers Dis. 2016 Mar 31;52(3):863-73. doi: 10.3233/JAD-150732. [Article]
  2. Heurling K, Leuzy A, Zimmer ER, Lubberink M, Nordberg A: Imaging beta-amyloid using [(18)F]flutemetamol positron emission tomography: from dosimetry to clinical diagnosis. Eur J Nucl Med Mol Imaging. 2016 Feb;43(2):362-73. doi: 10.1007/s00259-015-3208-1. Epub 2015 Oct 6. [Article]
  3. FDA Approved Drug Products: VIZAMYL (flutemetamol F 18) injection [Link]
KEGG Drug
D10231
PubChem Compound
15950376
PubChem Substance
310265064
ChemSpider
13092196
RxNav
1486025
ChEBI
76611
ChEMBL
CHEMBL2042122
ZINC
ZINC000100096928
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Flutemetamol_(18F)
FDA label
Download (4.64 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedDiagnosticAlzheimer's Disease (AD) and Related Disorders1
3CompletedDiagnosticAlzheimer's Disease (AD) / Mild Cognitive Impairment (MCI)1
3CompletedDiagnosticHealthy Volunteers (HV)1
3TerminatedDiagnosticAlzheimer's Disease (AD) / Dementia / Mild Cognitive Impairment (MCI)1
2Active Not RecruitingDiagnosticBreast Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous400 MBq/ml
SolutionIntravenous4.05 mCi/1mL
Injection, solutionIntravenous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7351401No2008-04-012023-01-24US flag
US8691185No2014-04-082023-01-24US flag
US7270800No2007-09-182027-04-14US flag
US8236282No2012-08-072024-05-21US flag
US8916131No2014-12-232028-09-16US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0135 mg/mLALOGPS
logP4.16ALOGPS
logP3.45Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.23Chemaxon
pKa (Strongest Basic)2.89Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area45.15 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity84.62 m3·mol-1Chemaxon
Polarizability28.19 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0avi-0490000000-135b62248f691bd3ae5a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-6243fc914b4f91dafdc1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-c1ecd8e36911090d2376
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0090000000-fb7d576ce5132913c83a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0590000000-849ac8a24a44e432dc32
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uk9-0290000000-32a1acc9ebd99ee9e249
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-0910000000-6c079de92eb0baa2bbcf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Binder
General Function
Transition metal ion binding
Specific Function
Functions as a cell surface receptor and performs physiological functions on the surface of neurons relevant to neurite growth, neuronal adhesion and axonogenesis. Involved in cell mobility and tra...
Gene Name
APP
Uniprot ID
P05067
Uniprot Name
Amyloid beta A4 protein
Molecular Weight
86942.715 Da
References
  1. Beach TG, Thal DR, Zanette M, Smith A, Buckley C: Detection of Striatal Amyloid Plaques with [18F]flutemetamol: Validation with Postmortem Histopathology. J Alzheimers Dis. 2016 Mar 31;52(3):863-73. doi: 10.3233/JAD-150732. [Article]

Drug created at October 01, 2015 19:41 / Updated at August 07, 2021 00:11