Fluciclovine (18F)

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Fluciclovine (18F)
Fluciclovine F-18.svg
Clinical data
Trade names Axumin
AHFS/Drugs.com Micromedex Detailed Consumer Information
License data
ATC code
Legal status
Legal status
Identifiers
  • trans-1-Amino-3-(18F)fluorocyclobutanecarboxylic acid
CAS Number
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
Formula C5H818FNO2
Molar mass 132.12g·mol−1
3D model (JSmol)
  • N[C@]1(C[C@H]([18F])C1)C(O)=O
  • 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]

Contents

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

  1. ↑ "Axumin- fluciclovine f-18 injection, solution". DailyMed. 8 December 2023. Retrieved 15 May 2024.
  2. ↑ "Axumin EPAR". European Medicines Agency (EMA). 22 May 2017. Retrieved 15 May 2024.
  3. 1 2 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.
  4. 1 2 Forrest W. "Start-up develops prostate PET agent." AuntMinnie.com 9 May 2014 Archived 1 December 2017 at the Wayback Machine
  5. 1 2 3 FDA Press Release. "FDA approves new diagnostic imaging agent to detect recurrent prostate cancer" 27 May 2016
  6. 1 2 Drugs.com "FDA Approves Axumin (fluciclovine F 18) Diagnostic Imaging Agent to Detect Recurrent Prostate Cancer" 27 May 2016
  7. ↑ Berberabe T. "FDA Approves Radioactive Imaging Agent Axumin in Recurrent Prostate Cancer." OncLive 27 May 2016
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ Bankhead C. "Prostate Scan Agent Approved by FDA." MedPage Today 27 May 2016
  12. 1 2 3 4 5 6 7 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.
  13. 1 2 3 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.
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