Identification
- Summary
Florbetapir (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
- Amyvid
- Generic Name
- Florbetapir (18F)
- DrugBank Accession Number
- DB09149
- Background
Florbetapir (18F) is a radiopharmaceutical compound containing the radionuclide fluorine-18 bound to the compound florbetapir, a molecule that binds with high affinity to beta amyloid plaque, a peptide that plays a key role in Alzheimer's Disease pathogenesis. Marketed as the product Amyvid, florbetapir 18F 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) and other causes of cognitive decline.
The radionucleide fluorine-18 was chosen as it has a half life of 110 minutes allowing it to accumulate sufficiently in the brain before undergoing positon emission decay.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Florbetapir (18F) (DB09149)
- Weight
- Average: 359.432
Monoisotopic: 359.18745534 - Chemical Formula
- C20H25FN2O3
- Synonyms
- [18F]Florbetapir
- 4-{(E)-2-[6-(2-{2-[2-(18F)fluoroethoxy]ethoxy}ethoxy)pyridin-3-yl]ethenyl}-N-methylaniline
- Florbetapir (18F)
- Florbetapir F-18
- Florbetapir F18
- florbetapir-fluorine-18
- External IDs
- (18F)AV-45
- 18F-AV-45
- 18FAV-45
- 18FAV45
- AV-45 F-18
Pharmacology
- Indication
Florbetapir 18F 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) 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 •••••••••••• - Contraindications & Blackbox Warnings
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Following intravenous injection, florbetapir F 18 diffuses across the human blood-brain barrier and produces a radioactivity signal detectable throughout the brain. Subsequently, cerebral perfusion decreases the brain florbetapir F 18 content, with differential retention of the drug in areas that contain β-amyloid aggregates compared to areas that lack the aggregates.
- Mechanism of action
Florbetapir (18F) is a radiopharmaceutical compound containing the radionuclide fluorine-18 bound to the compound florbetapir, a molecule that binds with high affinity to beta amyloid plaque, a peptide that plays a key role in Alzheimer's Disease pathogenesis. The radionucleide fluorine-18 was chosen as it has a half life of 110 minutes allowing it to accumulate sufficiently in the brain before undergoing positon emission decay.
Target Actions Organism AAmyloid beta A4 protein binderHumans - Absorption
The time-activity curves for florbetapir F 18 in the brain of subjects with positive scans show continual signal increases from time zero through 30 minutes post-administration, with stable values thereafter up to at least 90 minutes post-injection. Following the intravenous administration of 370 MBq (10 mCi) of florbetapir F 18 to healthy volunteers, the drug was distributed throughout the body with less than 5% of the injected F 18 radioactivity present in the blood by 20 minutes following administration, and less than 2% present by 45 minutes after administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
The residual F 18 in circulation during the 30-90 minute imaging window was principally in the form of polar F 18 metabolites. Essentially all radioactivity collected in the urine was present as polar metabolites of florbetapir F 18. Three metabolites have been discovered and identified as [18F]AV-160 (desmethyl-[18F]AV-45), [18F]AV-267 (N-acetyl–[18F]AV-160), and an [18F]-Polar species, the identity of which has not been confirmed. Additionally, although metabolites may make some contribution to signal detection, particularly to the nontarget activity, it is concluded that there will be minimal interference from these radiolabeled metabolites to the amyloid target binding in the [18F]AV-45 brain PET image (Wong et al, 2010).
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- Route of elimination
Whole body scanning following the intravenous injection showed accumulation of radioactivity in the liver within four minutes post-injection, followed by elimination of the radioactivity predominantly through the biliary/gastrointestinal tract with much lower radioactivity detected in the bladder. Essentially all radioactivity collected in the urine was present as polar metabolites of florbetapir F 18.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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The most common reported adverse reaction was headache, occurring in 2% of patients, followed by musculoskeletal pain, blood pressure increased, fatigue, nausea, and injection site reaction, all occurring in <1% of patients.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Florbetapir (18F) which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Florbetapir (18F) which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Florbetapir (18F) which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Florbetapir (18F) which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Florbetapir (18F) 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 Amyvid Injection, solution 1900 MBq/ml Intravenous Eli Lilly Nederland B.V. 2016-09-08 Not applicable EU 
Amyvid Injection, solution 800 MBq/ml Intravenous Eli Lilly Nederland B.V. 2016-09-08 Not applicable EU Amyvid Injection, solution 1900 MBq/ml Intravenous Eli Lilly Nederland B.V. 2016-09-08 Not applicable EU Amyvid Injection, solution 51 mCi/1mL Intravenous Eli Lilly and Company 2012-06-01 Not applicable US 
Amyvid Injection, solution 800 MBq/ml Intravenous Eli Lilly Nederland B.V. 2016-09-08 Not applicable EU
Categories
- ATC Codes
- V09AX05 — Florbetapir (18f)
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Styrenes
- Direct Parent
- Styrenes
- Alternative Parents
- Phenylalkylamines / Aniline and substituted anilines / Secondary alkylarylamines / Alkyl aryl ethers / Pyridines and derivatives / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organofluorides show 2 more
- Substituents
- Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Amine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Dialkyl ether / Ether / Heteroaromatic compound show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organofluorine compound, aromatic ether, substituted aniline, pyridines, fluorine-18 radiopharmaceutical (CHEBI:66880)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6W15Z5R0RU
- CAS number
- 956103-76-7
- InChI Key
- YNDIAUKFXKEXSV-CRYLGTRXSA-N
- InChI
- InChI=1S/C20H25FN2O3/c1-22-19-7-4-17(5-8-19)2-3-18-6-9-20(23-16-18)26-15-14-25-13-12-24-11-10-21/h2-9,16,22H,10-15H2,1H3/b3-2+/i21-1
- IUPAC Name
- 4-[(E)-2-[6-(2-{2-[2-(¹⁸F)fluoroethoxy]ethoxy}ethoxy)pyridin-3-yl]ethenyl]-N-methylaniline
- SMILES
- [H]N(C1=C([H])C([H])=C(\C([H])=C(/[H])C2=C([H])N=C(OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])C([H])([H])[18F])C([H])=C2[H])C([H])=C1[H])C([H])([H])[H]
References
- Synthesis Reference
- Wong DF, Rosenberg PB, Zhou Y, Kumar A, Raymont V, Ravert HT, Dannals RF, Nandi A, Brasic JR, Ye W, Hilton J, Lyketsos C, Kung HF, Joshi AD, Skovronsky DM, Pontecorvo MJ: In vivo imaging of amyloid deposition in Alzheimer disease using the radioligand 18F-AV-45 (florbetapir [corrected] F 18). J Nucl Med. 2010 Jun;51(6):913-20. doi: 10.2967/jnumed.109.069088.
- Fowler J. S. and Wolf A. P. (1982) The synthesis of carbon-11, fluorine-18 and nitrogen-13 labeled radiotracers for biomedical applications. Nucl. Sci. Ser. Natl Acad. Sci. Natl Res. Council Monogr. 1982.
- General References
- Wong DF, Rosenberg PB, Zhou Y, Kumar A, Raymont V, Ravert HT, Dannals RF, Nandi A, Brasic JR, Ye W, Hilton J, Lyketsos C, Kung HF, Joshi AD, Skovronsky DM, Pontecorvo MJ: In vivo imaging of amyloid deposition in Alzheimer disease using the radioligand 18F-AV-45 (florbetapir [corrected] F 18). J Nucl Med. 2010 Jun;51(6):913-20. doi: 10.2967/jnumed.109.069088. [Article]
- Choi SR, Golding G, Zhuang Z, Zhang W, Lim N, Hefti F, Benedum TE, Kilbourn MR, Skovronsky D, Kung HF: Preclinical properties of 18F-AV-45: a PET agent for Abeta plaques in the brain. J Nucl Med. 2009 Nov;50(11):1887-94. doi: 10.2967/jnumed.109.065284. Epub 2009 Oct 16. [Article]
- FDA Approved Drug Products: AMYVID (florbetapir F18) injection [Link]
- External Links
- KEGG Drug
- D09617
- PubChem Compound
- 24822371
- PubChem Substance
- 310265062
- ChemSpider
- 26348452
- BindingDB
- 50484946
- 1427224
- ChEBI
- 66880
- ChEMBL
- CHEMBL1774461
- ZINC
- ZINC000100090643
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Florbetapir_(18F)
- FDA label
- Download (4.31 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 4 Completed Diagnostic Alzheimer's Disease (AD) 4 4 Completed Other Multiple Sclerosis 1 4 Recruiting Diagnostic POCD - Postoperative Cognitive Dysfunction 1 4 Terminated Diagnostic Cardiac Amyloidosis 3 3 Completed Diagnostic Alzheimer's Disease (AD) 3
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 1900 MBQ/ml Injection, solution Intravenous 51 mCi/1mL Injection, solution Intravenous 800 MBQ/ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8506929 No 2013-08-13 2027-04-30 US US7687052 No 2010-03-30 2027-04-30 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0058 mg/mL ALOGPS logP 3.61 ALOGPS logP 3.11 Chemaxon logS -4.8 ALOGPS pKa (Strongest Basic) 4.62 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.61 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 103.01 m3·mol-1 Chemaxon Polarizability 40.43 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 splash10-03di-2049000000-85b69d65f7f6232bbc23 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01t9-6091000000-45696fddc16e315688c5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0fba-3091000000-29420739c289059b1fb9 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-1190000000-d853e6d74d72c697b060 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6v-3890000000-62ab5d34ea938f4429c7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00fr-1962000000-f82dc8ed39ab2f2e65aa 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
- 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
- Choi SR, Golding G, Zhuang Z, Zhang W, Lim N, Hefti F, Benedum TE, Kilbourn MR, Skovronsky D, Kung HF: Preclinical properties of 18F-AV-45: a PET agent for Abeta plaques in the brain. J Nucl Med. 2009 Nov;50(11):1887-94. doi: 10.2967/jnumed.109.065284. Epub 2009 Oct 16. [Article]
Drug created at October 01, 2015 17:14 / Updated at August 13, 2021 04:44