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Fluciclovine (18F)

Chemical compound From Wikipedia, the free encyclopedia

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]

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Fluciclovine (18
F
)
Clinical data
Trade namesAxumin
AHFS/Drugs.comMicromedex Detailed Consumer Information
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ATC code
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Identifiers
  • trans-1-Amino-3-(18F)fluorocyclobutanecarboxylic acid
CAS Number
DrugBank
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ChEMBL
Chemical and physical data
FormulaC5H818FNO2
Molar mass132.12 g·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
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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]

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