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Identification
NameFlutemetamol (18F)
Accession NumberDB09151  (DB09562)
TypeSmall Molecule
GroupsApproved
DescriptionFlutemetamol (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.
Structure
Thumb
Synonyms
2-[3-(18F)fluoro-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol
[18F]-Flutemetamol
flutemetamol (18F)
Flutemetamol F 18
Flutemetamol F-18
Flutemetamol F18
External IDs Not Available
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VizamylSolution4.05 mCi/mLIntravenousMedi Physics Inc.2014-01-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIL49M066S0O
CAS number765922-62-1
WeightAverage: 273.32
Monoisotopic: 273.060146823
Chemical FormulaC14H11FN2OS
InChI KeyVVECGOCJFKTUAX-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
Pharmacology
IndicationFlutemetamol 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.
Structured Indications
PharmacodynamicsFollowing 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 actionFluorine-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).
TargetKindPharmacological actionActionsOrganismUniProt ID
Amyloid beta A4 proteinProteinyes
binder
HumanP05067 details
Related Articles
AbsorptionThe 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 distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationExcretion was found to be approximately 37% renal and 52% hepatobiliary.
Half lifeNot Available
ClearanceNot Available
ToxicityMost commonly reported adverse reactions were flushing (2%), headache (1%), increased blood pressure (2%), nausea (1%), and dizziness (1%).
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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. [PubMed:27031469 ]
  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. [PubMed:26440450 ]
External Links
ATC CodesV09AX04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (4.64 MB)
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingBasic ScienceAlzheimer Disease1
2CompletedBasic ScienceAlzheimer's Disease (AD)1
3RecruitingDiagnosticAlzheimer's Disease (AD) and Related Disorders1
Not AvailableRecruitingNot AvailableAlzheimer's Disease (AD) / Dementias / Mild Cognitive Impairment (MCI)1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
SolutionIntravenous4.05 mCi/mL
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7270800 No2007-04-142027-04-14Us
US7351401 No2003-01-242023-01-24Us
US8236282 No2004-05-212024-05-21Us
US8691185 No2003-01-242023-01-24Us
US8916131 No2008-09-162028-09-16Us
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazoles
Sub ClassNot Available
Direct ParentBenzothiazoles
Alternative Parents
Substituents
  • 1,3-benzothiazole
  • Phenylalkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fluorobenzene
  • Halobenzene
  • Phenol
  • Secondary aliphatic/aromatic amine
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Azole
  • Thiazole
  • Azacycle
  • Secondary amine
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
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 transcription regulation through protein-protein interactions. Can promote transcription activation through binding to APBB1-KAT5 and inhibits Notch signaling through interaction with Numb. Couples to ap...
Gene Name:
APP
Uniprot ID:
P05067
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. [PubMed:27031469 ]
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Drug created on October 01, 2015 13:41 / Updated on April 24, 2017 04:39