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Fluciclovine (18F)

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Chemical compound

Pharmaceutical compound
Fluciclovine (F)
Clinical data
Trade namesAxumin
AHFS/Drugs.comMicromedex Detailed Consumer Information
License data
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • trans-1-Amino-3-(F)fluorocyclobutanecarboxylic acid
CAS Number
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC5H8FNO2
Molar mass132.12 g·mol
3D model (JSmol)
SMILES
  • N1(C()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 (F), also known as anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid (anti-3 FACBC), 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.

Background

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

Mechanism

Fluciclovine is a -tagged synthetic analog of the amino acid L-leucine. FACBC uptake by the tumor is related to functional activity of two amino acid transporters, specifically sodium-dependent system ASC, with a lesser contribution by sodium-independent system L. Although it is handled by the amino acid transporter system, it does not undergo terminally incorporative metabolism within the body. 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. There is low native brain uptake compared to FDG, which may enhance detection of brain metastases or primary brain tumors. The more intense native liver and pancreatic uptake seen with this agent would be expected to limit disease detection in those organs. FACBC has a short synthesis time and a long half-life, which eliminate the need for an onsite cyclotron.

Marketing

Axumin is marketed by Blue Earth Diagnostics, Ltd., United Kingdom.

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. ^ 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. ^ Forrest W. "Start-up develops prostate PET agent." AuntMinnie.com 9 May 2014 Archived 1 December 2017 at the Wayback Machine
  5. ^ FDA Press Release. "FDA approves new diagnostic imaging agent to detect recurrent prostate cancer" 27 May 2016
  6. ^ 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. ^ 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. ^ 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.
Diagnostic radiopharmaceuticals (V09)
Central nervous system
Skeletal system
Renal
Gastrointestinal/Hepatic
Respiratory system
Cardiovascular system
Inflammation/infection
Tumor
Adrenal cortex
Radionuclides
(including tracers)
positron (PET list)
gamma ray/photon (SPECT/scintigraphy)
Isotopes used: See also: Therapeutic radiopharmaceuticals (V10)
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