Identification
- Summary
Fluciclovine (18F) is a radiolabelled L-leucine derivative used to image tumors, especially in the prostate.
- Brand Names
- Axumin
- Generic Name
- Fluciclovine (18F)
- DrugBank Accession Number
- DB13146
- Background
Fluciclovine is a [18F]-tagged synthetic analog of the amino acid L-leucine. It presents excellent diagnostic properties to be used in positron emission tomography (PET) imaging.2 The structure of fluciclovine allows it to be uptaken by the tumoral cells by its amino acid transporter without incorporating in the metabolism within the body.3 Fluciclovine was developed by Blue Earth Diagnostics, Ltd. and FDA approved in May 27, 2016.7
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Fluciclovine (18F) (DB13146)
- Weight
- Average: 132.125
Monoisotopic: 132.056441169 - Chemical Formula
- C5H8FNO2
- Synonyms
- (18F)FACBC
- (1R,3R)-1-amino-3(18F)fluorocyclobutane-1-carboxylic acid
- Anti-1-amino-3-(18F)fluorocyclobutane-1-carboxylic acid
- FACBC F-18
- Fluciclovine (18F)
- Fluciclovine F 18
- Fluciclovine F-18
- External IDs
- (18F)GE-148
- GE-148 (18F)
- GE-148 F-18
- NMK-36
- NMK36
Pharmacology
- Indication
Fluciclovine is indicated as a detection agent for positron emission tomography (PET) in men with suspected prostate cancer recurrence based on elevated blood prostate specific antigen (PSA) levels following prior treatment.4 The overexpression of L-type amino acid transporters such as LAT1 and LAT3 that mediate the uptake of essential amino acids has been extensively reported as a tumoral mechanism of cell growth.5
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Prostate cancer •••••••••••• - Contraindications & Blackbox Warnings
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Following intravenous administration, the tumor-to-normal tissue contrast is highest between 2 and 10 minutes after injection, with a 63% reduction in mean tumor uptake at 90 minutes after injection.6 The scanning time point should be evaluated carefully as an early scanning can present an increased blood pool and a late scanning will translate into an increased muscle uptake. These variations should always be considered in the image interpretation.8
- Mechanism of action
Fluciclovine is transported into the prostate cancer cells via ASCT2 and LAT1 transporters. The activity of LAT1 gets increased in acidic pH, condition that is developed intra-tumorally at certain size. The uptake of fluciclovine presents an androgen-dependent dynamic in hormone sensitive cells.9
Target Actions Organism ANeutral amino acid transporter B(0) binderHumans AY+L amino acid transporter 1 binderHumans ACationic amino acid transporter 3 binderHumans NGlutamate (NMDA) receptor inhibitorHumans NGlutamate receptor 1 inhibitorHumans NGlutamate receptor 2 inhibitorHumans NGlutamate receptor 3 inhibitorHumans NGlutamate receptor 4 inhibitorHumans - Absorption
After intravenous administration of fluciclovine, the major distribution happens in liver (14%), red bone marrow (12%), lung (7%), myocardium (4%) and pancreas (3%). With increasing time, the dose gets distributed into skeletal muscle.9
- Volume of distribution
The compartmental volume of distribution of fluciclovine is in prostate 0.97 L, vesicle 0.79 L, red bone marrow 0.98 L, gluteus muscle 2.13 L and obturator muscle 2.23 L.6
- Protein binding
Pre clinical studies showed that fluciclovine does not bind to plasma proteins.10
- Metabolism
Fluciclovine is not metabolized and it is not incorporated into newly synthesized proteins.9
- Route of elimination
In the first four hours post-injection, 3% of administered dose is excreted in the urine which increases to 5% after 24 hours post-injection.9
- Half-life
Fluciclovine is a cyclotron produced radionuclide that decays by positron emission (ß+ decay, 96.7%) and orbital electron capture (3.3%) to stable oxygen 18 with a physical half-life of 109.7 minutes.1
- Clearance
Fluciclovine renal clearance and excretion is minimal.6
- Adverse Effects
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The hasn't been long-term carcinogenity or fertility studies in animals. Even though all reports have shown no mutagenicity, fluciclovine has the potential to be mutagenic.10
- 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.Not Available
- 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 Axumin Injection, solution 3200 MBq/ml Intravenous Blue Earth Diagnostics Ireland Ltd 2020-12-16 Not applicable EU 
Axumin Injection, solution 1600 MBq/ml Intravenous Blue Earth Diagnostics Ireland Ltd 2020-12-16 Not applicable EU Axumin Injection, solution 1600 MBq/ml Intravenous Blue Earth Diagnostics Ireland Ltd 2020-12-16 Not applicable EU Axumin Injection, solution 221 mCi/1mL Intravenous Blue Earth Diagnostics 2016-05-27 Not applicable US 
Axumin Injection, solution 3200 MBq/ml Intravenous Blue Earth Diagnostics Ireland Ltd 2020-12-16 Not applicable EU
Categories
- ATC Codes
- V09IX12 — Fluciclovine (18f)
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- L-alpha-amino acids
- Alternative Parents
- D-alpha-amino acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organofluorides / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds / Alkyl fluorides
- Substituents
- Aliphatic homomonocyclic compound / Alkyl fluoride / Alkyl halide / Amine / Amino acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Hydrocarbon derivative / L-alpha-amino acid
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 38R1Q0L1ZE
- CAS number
- 222727-39-1
- InChI Key
- NTEDWGYJNHZKQW-DGMDOPGDSA-N
- InChI
- InChI=1S/C5H8FNO2/c6-3-1-5(7,2-3)4(8)9/h3H,1-2,7H2,(H,8,9)/t3-,5-/i6-1
- IUPAC Name
- (1r,3r)-1-amino-3-(¹⁸F)fluorocyclobutane-1-carboxylic acid
- SMILES
- N[C@]1(C[C@H]([18F])C1)C(O)=O
References
- General References
- Nye JA, Schuster DM, Yu W, Camp VM, Goodman MM, Votaw JR: Biodistribution and radiation dosimetry of the synthetic nonmetabolized amino acid analogue anti-18F-FACBC in humans. J Nucl Med. 2007 Jun;48(6):1017-20. doi: 10.2967/jnumed.107.040097. Epub 2007 May 15. [Article]
- Schuster DM, Votaw JR, Nieh PT, Yu W, Nye JA, Master V, Bowman FD, Issa MM, Goodman MM: Initial experience with the radiotracer anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid with PET/CT in prostate carcinoma. J Nucl Med. 2007 Jan;48(1):56-63. [Article]
- Schiavina R, Brunocilla E, Martorana G: The new promise of FACBC position emission tomography/computed tomography in the localization of disease relapse after radical treatment for prostate cancer: are we turning to the right radiotracer? Eur Urol. 2014 Jan;65(1):255-6. doi: 10.1016/j.eururo.2013.08.053. Epub 2013 Aug 30. [Article]
- Schuster DM, Nanni C, Fanti S: PET Tracers Beyond FDG in Prostate Cancer. Semin Nucl Med. 2016 Nov;46(6):507-521. doi: 10.1053/j.semnuclmed.2016.07.005. Epub 2016 Sep 7. [Article]
- Wang Q, Bailey CG, Ng C, Tiffen J, Thoeng A, Minhas V, Lehman ML, Hendy SC, Buchanan G, Nelson CC, Rasko JE, Holst J: Androgen receptor and nutrient signaling pathways coordinate the demand for increased amino acid transport during prostate cancer progression. Cancer Res. 2011 Dec 15;71(24):7525-36. doi: 10.1158/0008-5472.CAN-11-1821. Epub 2011 Oct 17. [Article]
- Sorensen J, Owenius R, Lax M, Johansson S: Regional distribution and kinetics of [18F]fluciclovine (anti-[18F]FACBC), a tracer of amino acid transport, in subjects with primary prostate cancer. Eur J Nucl Med Mol Imaging. 2013 Feb;40(3):394-402. doi: 10.1007/s00259-012-2291-9. Epub 2012 Dec 4. [Article]
- FDA News and Events [Link]
- Axumin [Link]
- Axumin [Link]
- FDA Reports [Link]
- FDA Approved Drug Products: AXUMIN (fluciclovine F 18) injection [Link]
- External Links
- PubChem Compound
- 450601
- PubChem Substance
- 347829262
- ChemSpider
- 23313216
- 1796118
- ChEBI
- 134703
- ChEMBL
- CHEMBL254468
- ZINC
- ZINC000101525552
- Wikipedia
- Fluciclovine_(18F)
- FDA label
- Download (265 KB)
- MSDS
- Download (116 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Recruiting Diagnostic Prostate Cancer 1 4 Terminated Diagnostic Cervical Cancer / Uterine Malignancies 1 4 Terminated Diagnostic Metastatic Carcinoma of the Prostate / Stage IVB Prostate Cancer AJCC v8 1 4 Unknown Status Diagnostic Cervical Cancer / Endometrial Cancer / Epithelial Ovarian Cancer 1 3 Completed Diagnostic Brain Metastases 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 1600 MBq/ml Injection, solution Intravenous 221 mCi/1mL Injection, solution Intravenous 3200 MBq/ml Injection, solution Intravenous bolus 1600 MBq/ml Injection, solution Intravenous bolus 3200 MBq/ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5808146 No 1998-09-15 2017-11-09 US US9387266 No 2016-07-12 2026-11-28 US US10010632 No 2018-07-03 2026-11-28 US US10124079 No 2018-11-13 2035-12-30 US US10716868 No 2020-07-21 2035-12-30 US US10933147 No 2021-03-02 2035-12-30 US US10967077 No 2021-04-06 2035-12-30 US US10953112 No 2021-03-23 2026-11-28 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 0ºC MSDS boiling point (°C) 100ºC MSDS water solubility Soluble MSDS Radioactivity (mCi/mL) 10 FDA label - Predicted Properties
Property Value Source Water Solubility 173.0 mg/mL ALOGPS logP -3 ALOGPS logP -2.9 Chemaxon logS 0.11 ALOGPS pKa (Strongest Acidic) 2.07 Chemaxon pKa (Strongest Basic) 9.42 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 27.75 m3·mol-1 Chemaxon Polarizability 11.65 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No 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 splash10-000l-9000000000-40609361b84eed0ac7ea Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-9100000000-10cfdfda5bd301d52b0d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0900000000-cd5988cd08de5aa795a6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00y1-9100000000-18b2fb07bac4d2cdba5e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0159-9700000000-7bb228f93147807f66bc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0007-9000000000-f52f81bef893fd7cc131 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-06y7-9000000000-4e230d26b14c008a646f 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
- Virus receptor activity
- Specific Function
- Sodium-dependent amino acids transporter that has a broad substrate specificity, with a preference for zwitterionic amino acids. It accepts as substrates all neutral amino acids, including glutamin...
- Gene Name
- SLC1A5
- Uniprot ID
- Q15758
- Uniprot Name
- Neutral amino acid transporter B(0)
- Molecular Weight
- 56597.64 Da
References
- Axumin [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- L-amino acid transmembrane transporter activity
- Specific Function
- Involved in the sodium-independent uptake of dibasic amino acids and sodium-dependent uptake of some neutral amino acids. Requires coexpression with SLC3A2/4F2hc to mediate the uptake of arginine, ...
- Gene Name
- SLC7A7
- Uniprot ID
- Q9UM01
- Uniprot Name
- Y+L amino acid transporter 1
- Molecular Weight
- 55990.01 Da
References
- Axumin [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- L-ornithine transmembrane transporter activity
- Specific Function
- Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
- Gene Name
- SLC7A3
- Uniprot ID
- Q8WY07
- Uniprot Name
- Cationic amino acid transporter 3
- Molecular Weight
- 67168.31 Da
References
- Axumin [Link]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Voltage-gated cation channel activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Components:
References
- FDA Reports [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Pdz domain binding
- Specific Function
- Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
- Gene Name
- GRIA1
- Uniprot ID
- P42261
- Uniprot Name
- Glutamate receptor 1
- Molecular Weight
- 101505.245 Da
References
- FDA Reports [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Ionotropic glutamate receptor activity
- Specific Function
- Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
- Gene Name
- GRIA2
- Uniprot ID
- P42262
- Uniprot Name
- Glutamate receptor 2
- Molecular Weight
- 98820.32 Da
References
- FDA Reports [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Extracellular-glutamate-gated ion channel activity
- Specific Function
- Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
- Gene Name
- GRIA3
- Uniprot ID
- P42263
- Uniprot Name
- Glutamate receptor 3
- Molecular Weight
- 101155.975 Da
References
- FDA Reports [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Ionotropic glutamate receptor activity
- Specific Function
- Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
- Gene Name
- GRIA4
- Uniprot ID
- P48058
- Uniprot Name
- Glutamate receptor 4
- Molecular Weight
- 100870.085 Da
References
- FDA Reports [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- May be an organic anion pump relevant to cellular detoxification.
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- FDA Reports [Link]
Drug created at November 16, 2016 15:20 / Updated at October 01, 2021 23:55