NAV

Florbetaben F-18

Identification

Summary

Florbetaben F-18 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
Neuraceq
Generic Name
Florbetaben F-18
DrugBank Accession Number
DB09148
Background

Florbetaben is a fluorine-18 (18F)-labeled stilbene derivative used for Positron Emission Tomography (PET) imaging of the brain. It is used for the non-invasive detection of the density of ß-amyloid neuritic plaques in the brain of adult patients with cognitive impairment.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 358.444
Monoisotopic: 358.192206368
Chemical Formula
C21H26FNO3
Synonyms
  • 4-((1E)-2-(4-(2-(2-(2-((SUP 18(F))FLUOROETHOXY)ETHOXY)ETHOXY)PHENYL)ETH-1-EN-1-YL)-N-METHYLANILINE
  • Florbetaben (18F)
  • florbetaben (¹⁸F)
  • florbetaben F18
  • FLORBETABEN(18F)
External IDs
  • AV-1
  • BAY-94-9172
  • BAY-949172
  • BAY94-9172
  • ZK-6013443
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Pharmacology

Indication

Florbetaben is a radioactive diagnostic agent 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) and 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 administration, Neuraceq crosses the blood brain barrier and shows differential retention in brain regions that contain β-amyloid deposits. Differences in signal intensity between brain regions showing specific and non-specific Neuraceq uptake form the basis for the image interpretation method.

Mechanism of action

Florbetaben F18 is a F18-labeled stilbene derivative, which binds to β-amyloid plaques in the brain. The F 18 isotope produces a positron signal that is detected by a PET scanner.

TargetActionsOrganism
AAmyloid beta A4 protein
binder
Humans
Absorption

Ten minutes after intravenous bolus injection of 300 MBq of Neuraceq in human volunteers, approximately 6% of the injected radioactivity was distributed to the brain. Florbetaben F 18 plasma concentrations declined by approximately 75% at 20 minutes post-injection, and by approximately 90% at 50 minutes.

Volume of distribution

Not Available

Protein binding

Florbetaben is 98.5% bound to plasma proteins.

Metabolism

In vitro studies show that metabolism of florbetaben is predominantly catalyzed by CYP2J2 and CYP4F2. Almost all F18 radioactivity in urine was excreted as polar metabolites of florbetaben F18 and only trace amounts of florbetaben F18 were detected.

Route of elimination

At 12 hours post-administration, approximately 30% of the injected radioactivity had been excreted in urine.

Half-life

1 hr

Clearance

Not Available

Adverse Effects
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Toxicity

The most commonly reported adverse reactions were: injection site reaction consisting of erythema (1.7 %), irritation (1.2 %), and pain (3.9 %).

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAbacavir may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Florbetaben (18F) which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NeuraceqInjection, solution300 MBq/mlIntravenousLife Radiopharma Berlin Gmb H2016-09-08Not applicableEU flag
NeuraceqInjection, solution135 mCi/1mLIntravenousLife Molecular Imaging, Ltd2014-03-20Not applicableUS flag

Categories

ATC Codes
V09AX06 — Florbetaben (18f)
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Styrenes / Phenylalkylamines / Phenoxy compounds / Phenol ethers / Aniline and substituted anilines / Secondary alkylarylamines / Alkyl aryl ethers / Dialkyl ethers / Organopnictogen compounds / Organofluorides
show 2 more
Substituents
Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Amine / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzenoid / Dialkyl ether / Ether / Hydrocarbon derivative
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, substituted aniline, secondary amino compound, polyether, fluorine-18 radiopharmaceutical, stilbenoid (CHEBI:79033)
Affected organisms
Not Available

Chemical Identifiers

UNII
TLA7312TOI
CAS number
902143-01-5
InChI Key
NCWZOASIUQVOFA-FWZJPQCDSA-N
InChI
InChI=1S/C21H26FNO3/c1-23-20-8-4-18(5-9-20)2-3-19-6-10-21(11-7-19)26-17-16-25-15-14-24-13-12-22/h2-11,23H,12-17H2,1H3/b3-2+/i22-1
IUPAC Name
4-[(E)-2-[4-(2-{2-[2-(¹⁸F)fluoroethoxy]ethoxy}ethoxy)phenyl]ethenyl]-N-methylaniline
SMILES
CNC1=CC=C(\C=C\C2=CC=C(OCCOCCOCC[18F])C=C2)C=C1

References

General References
  1. Syed YY, Deeks E: [(18)F]Florbetaben: a review in beta-amyloid PET imaging in cognitive impairment. CNS Drugs. 2015 Jul;29(7):605-13. doi: 10.1007/s40263-015-0258-7. [Article]
  2. Sabri O, Sabbagh MN, Seibyl J, Barthel H, Akatsu H, Ouchi Y, Senda K, Murayama S, Ishii K, Takao M, Beach TG, Rowe CC, Leverenz JB, Ghetti B, Ironside JW, Catafau AM, Stephens AW, Mueller A, Koglin N, Hoffmann A, Roth K, Reininger C, Schulz-Schaeffer WJ: Florbetaben PET imaging to detect amyloid beta plaques in Alzheimer's disease: phase 3 study. Alzheimers Dement. 2015 Aug;11(8):964-74. doi: 10.1016/j.jalz.2015.02.004. Epub 2015 Mar 28. [Article]
  3. Zhang W, Oya S, Kung MP, Hou C, Maier DL, Kung HF: F-18 Polyethyleneglycol stilbenes as PET imaging agents targeting Abeta aggregates in the brain. Nucl Med Biol. 2005 Nov;32(8):799-809. [Article]
KEGG Drug
D10002
PubChem Compound
11501341
PubChem Substance
310265061
ChemSpider
9676143
RxNav
1492940
ChEBI
79033
ChEMBL
CHEMBL566752
ZINC
ZINC000100529288
RxList
RxList Drug Page
Wikipedia
Florbetaben_(18F)
FDA label
Download (3.7 MB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchAlzheimer's Disease (AD)1
3CompletedDiagnosticAlzheimer's Disease (AD)1
3RecruitingDiagnosticCardiac Amyloidosis / Primary Amyloidosis / Transthyretin Mediated Amyloidosis (ATTR)1
2CompletedDiagnosticAlzheimer's Disease (AD) / Amyloid Beta Protein1
2CompletedDiagnosticAmyloid Beta Protein / Down Syndrome (DS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous135 mCi/1mL
Injection, solutionIntravenous300 MBQ/ml
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7807135No2010-10-052029-03-18US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00103 mg/mLALOGPS
logP4.2ALOGPS
logP3.74Chemaxon
logS-5.5ALOGPS
pKa (Strongest Basic)4.62Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area39.72 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity104.86 m3·mol-1Chemaxon
Polarizability41.65 Å3Chemaxon
Number of Rings2Chemaxon
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ka-7097000000-66ac1a4e8919ae410812
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-5090000000-64045a7dcb825d6870b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1090000000-076f54570b696d48282d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002k-6090000000-09bc017f4a496f9dbe09
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fu-5790000000-04773fdd272e0c9d9fb5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02cr-3941000000-a4064799f119f27b4f00
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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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

Enzymes

Details1. Cytochrome P450 2J2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
Molecular Weight
57610.165 Da
Details2. Leukotriene-B(4) omega-hydroxylase 1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
Not Available
Gene Name
CYP4F2
Uniprot ID
P78329
Uniprot Name
Phylloquinone omega-hydroxylase CYP4F2
Molecular Weight
59852.825 Da

Drug created at October 01, 2015 17:06 / Updated at September 15, 2023 10:37