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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
Structure for Florbetaben F-18 (DB09148)
- 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
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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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Alzheimer's disease •••••••••••• Diagnostic agent Cognitive decline •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AAmyloid-beta precursor protein binderHumans - 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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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
- 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 softwareAbacavir Abacavir may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Florbetaben (18F) which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Florbetaben F-18 which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Neuraceq Injection, solution 300 MBq/ml Intravenous Life Molecular Imaging Gmbh 2016-09-08 Not applicable EU 
Neuraceq Injection, solution 135 mCi/1mL Intravenous Life Molecular Imaging Gmbh 2014-03-20 Not applicable US 
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
- 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]
- 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]
- 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]
- External Links
- KEGG Drug
- D10002
- PubChem Compound
- 11501341
- PubChem Substance
- 310265061
- ChemSpider
- 9676143
- 1492940
- ChEBI
- 79033
- ChEMBL
- CHEMBL566752
- ZINC
- ZINC000100529288
- RxList
- RxList Drug Page
- Wikipedia
- Florbetaben_(18F)
- FDA label
- Download (3.7 MB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Alzheimer's Disease (AD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Alzheimer's Disease (AD) / Dementia 1 somestatus stop reason just information to hide Not Available Completed Not Available Alzheimer's Disease (AD) / Primary Progressive Aphasia(PPA) 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Alzheimer's Disease (AD) / Brain Disorders / Central Nervous System Disorder / Dementia / Diseases of the Nervous System / Neurocognitive Disorders / Neurodegenerative Disorders / Psychiatric Disorder NOS / Tauopathies 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Alzheimer's Disease, Late Onset 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 135 mCi/1mL Injection, solution Intravenous 300 MBQ/ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7807135 No 2010-10-05 2029-03-18 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00103 mg/mL ALOGPS logP 4.2 ALOGPS logP 3.74 Chemaxon logS -5.5 ALOGPS pKa (Strongest Basic) 4.62 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 39.72 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 104.86 m3·mol-1 Chemaxon Polarizability 41.65 Å3 Chemaxon Number of Rings 2 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 MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03ka-7097000000-66ac1a4e8919ae410812 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-5090000000-64045a7dcb825d6870b0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1090000000-076f54570b696d48282d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-002k-6090000000-09bc017f4a496f9dbe09 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05fu-5790000000-04773fdd272e0c9d9fb5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-02cr-3941000000-a4064799f119f27b4f00 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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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Functions as a cell surface receptor and performs physiological functions on the surface of neurons relevant to neurite growth, neuronal adhesion and axonogenesis. Interaction between APP molecules on neighboring cells promotes synaptogenesis (PubMed:25122912). 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 apoptosis-inducing pathways such as those mediated by G(o) and JIP. Inhibits G(o) alpha ATPase activity (By similarity). Acts as a kinesin I membrane receptor, mediating the axonal transport of beta-secretase and presenilin 1 (By similarity). By acting as a kinesin I membrane receptor, plays a role in axonal anterograde transport of cargo towards synapses in axons (PubMed:17062754, PubMed:23011729). Involved in copper homeostasis/oxidative stress through copper ion reduction. In vitro, copper-metallated APP induces neuronal death directly or is potentiated through Cu(2+)-mediated low-density lipoprotein oxidation. Can regulate neurite outgrowth through binding to components of the extracellular matrix such as heparin and collagen I and IV. The splice isoforms that contain the BPTI domain possess protease inhibitor activity. Induces a AGER-dependent pathway that involves activation of p38 MAPK, resulting in internalization of amyloid-beta peptide and leading to mitochondrial dysfunction in cultured cortical neurons. Provides Cu(2+) ions for GPC1 which are required for release of nitric oxide (NO) and subsequent degradation of the heparan sulfate chains on GPC1
- Specific Function
- DNA binding
- Gene Name
- APP
- Uniprot ID
- P05067
- Uniprot Name
- Amyloid-beta precursor protein
- Molecular Weight
- 86942.715 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) in the cardiovascular system (PubMed:19965576, PubMed:8631948). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:19965576, PubMed:8631948). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:8631948). Converts arachidonic acid to four regioisomeric epoxyeicosatrienoic acids (EpETrE), likely playing a major role in the epoxidation of endogenous cardiac arachidonic acid pools (PubMed:8631948). In endothelial cells, participates in eicosanoids metabolism by converting hydroperoxide species into hydroxy epoxy metabolites. In combination with 15-lipoxygenase metabolizes arachidonic acid and converts hydroperoxyicosatetraenoates (HpETEs) into hydroxy epoxy eicosatrienoates (HEETs), which are precursors of vasodilatory trihydroxyicosatrienoic acids (THETAs). This hydroperoxide isomerase activity is NADPH- and O2-independent (PubMed:19737933). Catalyzes the monooxygenation of a various xenobiotics, such as danazol, amiodarone, terfenadine, astemizole, thioridazine, tamoxifen, cyclosporin A and nabumetone (PubMed:19923256). Catalyzes hydroxylation of the anthelmintics albendazole and fenbendazole (PubMed:23959307). Catalyzes the sulfoxidation of fenbedazole (PubMed:19923256)
- Specific Function
- arachidonic acid 11,12-epoxygenase activity
- Gene Name
- CYP2J2
- Uniprot ID
- P51589
- Uniprot Name
- Cytochrome P450 2J2
- Molecular Weight
- 57610.165 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, eicosanoids and vitamins (PubMed:10660572, PubMed:10833273, PubMed:11997390, PubMed:17341693, PubMed:18574070, PubMed:18577768). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase). Catalyzes predominantly the oxidation of the terminal carbon (omega-oxidation) of long- and very long-chain fatty acids. Displays high omega-hydroxylase activity toward polyunsaturated fatty acids (PUFAs) (PubMed:18577768). Participates in the conversion of arachidonic acid to omega-hydroxyeicosatetraenoic acid (20-HETE), a signaling molecule acting both as vasoconstrictive and natriuretic with overall effect on arterial blood pressure (PubMed:10660572, PubMed:17341693, PubMed:18574070). Plays a role in the oxidative inactivation of eicosanoids, including both pro-inflammatory and anti-inflammatory mediators such as leukotriene B4 (LTB4), lipoxin A4 (LXA4), and several HETEs (PubMed:10660572, PubMed:10833273, PubMed:17341693, PubMed:18574070, PubMed:18577768, PubMed:8026587, PubMed:9799565). Catalyzes omega-hydroxylation of 3-hydroxy fatty acids (PubMed:18065749). Converts monoepoxides of linoleic acid leukotoxin and isoleukotoxin to omega-hydroxylated metabolites (PubMed:15145985). Contributes to the degradation of very long-chain fatty acids (VLCFAs) by catalyzing successive omega-oxidations and chain shortening (PubMed:16547005, PubMed:18182499). Plays an important role in vitamin metabolism by chain shortening. Catalyzes omega-hydroxylation of the phytyl chain of tocopherols (forms of vitamin E), with preference for gamma-tocopherols over alpha-tocopherols, thus promoting retention of alpha-tocopherols in tissues (PubMed:11997390). Omega-hydroxylates and inactivates phylloquinone (vitamin K1), and menaquinone-4 (MK-4, a form of vitamin K2), both acting as cofactors in blood coagulation (PubMed:19297519, PubMed:24138531)
- Specific Function
- 20-aldehyde-leukotriene B4 20-monooxygenase activity
- Gene Name
- CYP4F2
- Uniprot ID
- P78329
- Uniprot Name
- Cytochrome P450 4F2
- Molecular Weight
- 59852.825 Da
Drug created at October 01, 2015 17:06 / Updated at September 15, 2023 10:37