Fluciclovine (18F)

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]

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[1] EU: Rx-only[2]
Identifiers
IUPAC name trans-1-Amino-3-(18F)fluorocyclobutanecarboxylic acid
CAS Number	222727-39-1 Y
DrugBank	DB15237
ChemSpider	23313216
UNII	38R1Q0L1ZE
KEGG	D10860 Y
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

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]