PROFILPELAJAR.COM

Fluciclovine (¹⁸F)
Clinical data
Trade names	Axumin
AHFS/Drugs.com	Micromedex Detailed Consumer Information
License data	US DailyMed: Fluciclovine;
ATC code	V09IX12 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only;
Identifiers
	IUPAC name trans-1-Amino-3-(18F)fluorocyclobutanecarboxylic acid;
CAS Number	222727-39-1 ;
DrugBank	DB15237;
ChemSpider	23313216;
UNII	38R1Q0L1ZE;
KEGG	D10860 ;
ChEBI	CHEBI:134703;
ChEMBL	ChEMBL254468;
Chemical and physical data
Formula	C5H818FNO2
Molar mass	132.12 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N[C@]1(C[C@H]([18F])C1)C(O)=O;
	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; Key:NTEDWGYJNHZKQW-DGMDOPGDSA-N;

Fluciclovine (¹⁸F), also known as anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid (anti-3[18F] FACBC),^[3]^[4] and sold under the brand name Axumin, is a diagnostic agent used for positron emission tomography (PET) imaging in men with suspected prostate cancer recurrence based on elevated prostate specific antigen (PSA) levels.^[5]^[6]

Background

Most imaging tests have not been able to localize recurrent prostate cancer when the PSA is mildly increased.^[3]^[5] Axumin scans were compared to [¹¹C]-tagged choline PET scans, another FDA approved PET scan that can assist in this situation, and to biopsy results.^[5]^[7] Fluciclovine tagged PET scans appear to more sensitive than CT scans^[8] and to [¹¹C]-tagged choline PET scans.^[9]^[10]

Mechanism

Fluciclovine is a [¹⁸F]-tagged synthetic analog of the amino acid L-leucine.^[11]^[12] FACBC uptake by the tumor is related to functional activity of two amino acid transporters,^[13] specifically sodium-dependent system ASC, with a lesser contribution by sodium-independent system L.^[12] Although it is handled by the amino acid transporter system, it does not undergo terminally incorporative metabolism within the body.^[12] The distribution of the tracer in the body differs from choline and FDG, as kidney uptake of FACBC is negligible, and no activity is found in the urinary tract.^[12]^[13] There is low native brain uptake compared to FDG, which may enhance detection of brain metastases^[4]^[12] or primary brain tumors.^[12] The more intense native liver and pancreatic uptake seen with this agent would be expected to limit disease detection in those organs.^[12] FACBC has a short synthesis time and a long half-life, which eliminate the need for an onsite cyclotron.^[13]

Marketing

Axumin is marketed by Blue Earth Diagnostics, Ltd., United Kingdom.^[6]

References

^ "Axumin- fluciclovine f-18 injection, solution". DailyMed. 8 December 2023. Retrieved 15 May 2024.
^ "Axumin EPAR". European Medicines Agency (EMA). 22 May 2017. Retrieved 15 May 2024.
^ ^a ^b Schiavina R, Ceci F, Borghesi M, et al. (2013). "The dilemma of localizing disease relapse after radical treatment for prostate cancer: which is the value of the actual imaging techniques?". Curr Radiopharm. 6 (2): 92–5. doi:10.2174/1874471011306020005. PMID 23597246.
^ ^a ^b Forrest W. "Start-up develops prostate PET agent." AuntMinnie.com 9 May 2014 [1] Archived 1 December 2017 at the Wayback Machine
^ ^a ^b ^c FDA Press Release. "FDA approves new diagnostic imaging agent to detect recurrent prostate cancer" 27 May 2016 [2]
^ ^a ^b Drugs.com "FDA Approves Axumin (fluciclovine F 18) Diagnostic Imaging Agent to Detect Recurrent Prostate Cancer" 27 May 2016 [3]
^ Berberabe T. "FDA Approves Radioactive Imaging Agent Axumin in Recurrent Prostate Cancer." OncLive 27 May 2016 [4]
^ Odewole OA, Tade FI, Nieh PT, et al. (2016). "Recurrent prostate cancer detection with anti-3-[(18)F]FACBC PET/CT: comparison with CT". Eur. J. Nucl. Med. Mol. Imaging. 43 (10): 1773–1783. doi:10.1007/s00259-016-3383-8. PMC 4970909. PMID 27091135.
^ Evangelista L, Briganti A, Fanti S, et al. (2016). "New Clinical Indications for (18)F/(11)C-choline, New Tracers for Positron Emission Tomography and a Promising Hybrid Device for Prostate Cancer Staging: A Systematic Review of the Literature". Eur. Urol. 70 (1): 161–75. doi:10.1016/j.eururo.2016.01.029. PMID 26850970.
^ Nanni C, Schiavina R, Brunocilla E, et al. (2015). "18F-Fluciclovine PET/CT for the Detection of Prostate Cancer Relapse: A Comparison to 11C-Choline PET/CT". Clin Nucl Med. 40 (8): e386–91. doi:10.1097/RLU.0000000000000849. PMID 26053708. S2CID 31082439.
^ Bankhead C. "Prostate Scan Agent Approved by FDA." MedPage Today 27 May 2016 [5]
^ ^a ^b ^c ^d ^e ^f ^g Schuster DM, Nanni C, Fanti S, et al. (2014). "Anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid: physiologic uptake patterns, incidental findings, and variants that may simulate disease". J. Nucl. Med. 55 (12): 1986–92. doi:10.2967/jnumed.114.143628. PMC 4844004. PMID 25453047.
^ ^a ^b ^c Schiavina R, Brunocilla E, Martorana G (2014). "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. 65 (1): 255–6. doi:10.1016/j.eururo.2013.08.053. PMID 24094575.