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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Flutemetamol (18F) (DB09151)

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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

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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 Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Diagnostic agent	Alzheimer's disease		••••••••••••
Diagnostic agent	Cognitive decline		••••••••••••

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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).

Target	Actions	Organism
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

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Not Available

Interactions

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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.

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Vizamyl	Solution	4.05 mCi/1mL	Intravenous	Medi-Physics, Inc. dba GE Healthcare	2014-01-01	Not applicable
Vizamyl	Injection, solution	400 MBq/mL	Intravenous	Ge Healthcare As	2021-02-10	Not applicable
Vizamyl	Injection, solution	400 MBq/mL	Intravenous	Ge Healthcare As	2021-02-10	Not applicable

Categories

ATC Codes

V09AX04 — Flutemetamol (18f)

• V09AX — Other central nervous system diagnostic radiopharmaceuticals
• V09A — CENTRAL NERVOUS SYSTEM
• V09 — DIAGNOSTIC RADIOPHARMACEUTICALS
• V — VARIOUS

Drug Categories

• Amines
• Central Nervous System
• Compounds used in a research, industrial, or household setting
• Contrast Media
• Diagnostic Radiopharmaceuticals
• Diagnostic Uses of Chemicals
• Heterocyclic Compounds, Fused-Ring
• Indicators and Reagents
• Laboratory Chemicals
• Radioactive Diagnostic Agent
• Radiopharmaceutical Activity
• Radiopharmaceuticals
• Sulfur Compounds
• Thiazoles

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 / Organooxygen compounds / Organofluorides / Hydrocarbon derivatives

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Substituents

1,3-benzothiazole / 1-hydroxy-2-unsubstituted benzenoid / Amine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Fluorobenzene / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxygen compound / Organofluoride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenylalkylamine / Secondary aliphatic/aromatic amine / Secondary amine / Thiazole

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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]

External Links

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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
3	Completed	Diagnostic	Alzheimer's Disease (AD) and Related Disorders	1
3	Completed	Diagnostic	Alzheimer's Disease (AD) / Mild Cognitive Impairment (MCI)	1
3	Completed	Diagnostic	Healthy Subjects (HS)	1
3	Terminated	Diagnostic	Alzheimer's Disease (AD) / Dementia / Mild Cognitive Impairment (MCI)	1
2	Active Not Recruiting	Diagnostic	Breast Cancer	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, solution	Intravenous	400 MBq/ml
Solution	Intravenous	4.05 mCi/1mL
Injection, solution	Intravenous

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7351401	No	2008-04-01	2023-01-24
US8691185	No	2014-04-08	2023-01-24
US7270800	No	2007-09-18	2027-04-14
US8236282	No	2012-08-07	2024-05-21
US8916131	No	2014-12-23	2028-09-16

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0135 mg/mL	ALOGPS
logP	4.16	ALOGPS
logP	3.45	Chemaxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.23	Chemaxon
pKa (Strongest Basic)	2.89	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	45.15 Å2	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	84.62 m3·mol-1	Chemaxon
Polarizability	28.19 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0avi-0490000000-135b62248f691bd3ae5a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0090000000-6243fc914b4f91dafdc1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0090000000-c1ecd8e36911090d2376
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0fk9-0090000000-fb7d576ce5132913c83a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0590000000-849ac8a24a44e432dc32
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uk9-0290000000-32a1acc9ebd99ee9e249
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00xr-0910000000-6c079de92eb0baa2bbcf
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Amyloid beta A4 protein

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]

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