Fluciclovine (18F)

Short description: Chemical compound

Fluciclovine (18F)

Clinical data
Trade names| Axumin
License data|

* EU EMA: by INN
* US DailyMed: Fluciclovine
* US FDA: Fluciclovine

ATC code|

* V09IX12 (WHO)

Legal status
Legal status|

* EU: Rx-only

Identifiers

IUPAC name

* trans-1-Amino-3-(18F)fluorocyclobutanecarboxylic acid

CAS Number|

* 222727-39-1 Y

ChemSpider|

* 23313216

UNII|

* 38R1Q0L1ZE

KEGG|

* D10860 Y

ChEBI|

* CHEBI:134703

Chemical and physical data
Formula| C5H818FNO2
Molar mass| 132.12 g/mol

Fluciclovine (18F), also known as anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid (anti-3[18F] FACBC),[1][2] or as Axumin (brand name), is a diagnostic agent indicated for positron emission tomography (PET) imaging in men with suspected prostate cancer recurrence based on elevated prostate specific antigen (PSA) levels.[3][4]

## Contents

* 1 Background
* 2 Mechanism
* 3 Marketing
* 4 References
* 5 External links

## Background

Most imaging tests have not been able to localize recurrent prostate cancer when the PSA is mildly increased.[1][3] 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.[3][5] Fluciclovine tagged PET scans appear to more sensitive than CT scans[6] and to [11C]-tagged choline PET scans.[7][8]

## Mechanism

Fluciclovine is a [18F]-tagged synthetic analog of the amino acid L-leucine.[9][10] FACBC uptake by the tumor is related to functional activity of two amino acid transporters,[11] specifically sodium-dependent system ASC, with a lesser contribution by sodium-independent system L.[10] Although it is handled by the amino acid transporter system, it does not undergo terminally incorporative metabolism within the body.[10] 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.[10][11] There is low native brain uptake compared to FDG, which may enhance detection of brain metastases[2][10] or primary brain tumors.[10] The more intense native liver and pancreatic uptake seen with this agent would be expected to limit disease detection in those organs.[10] FACBC has a short synthesis time and a long half-life, which eliminate the need for an onsite cyclotron.[11]

## Marketing

Axumin is marketed by Blue Earth Diagnostics, Ltd., United Kingdom.[4]

## References

1. ↑ 1.0 1.1 "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. 2013. doi:10.2174/1874471011306020005. PMID 23597246.
2. ↑ 2.0 2.1 Forrest W. "Start-up develops prostate PET agent." AuntMinnie.com May 9, 2014 [1]
3. ↑ 3.0 3.1 3.2 FDA Press Release. "FDA approves new diagnostic imaging agent to detect recurrent prostate cancer" May 27, 2016 [2]
4. ↑ 4.0 4.1 Drugs.com "FDA Approves Axumin (fluciclovine F 18) Diagnostic Imaging Agent to Detect Recurrent Prostate Cancer" May 27, 2016 [3]
5. ↑ Berberabe T. "FDA Approves Radioactive Imaging Agent Axumin in Recurrent Prostate Cancer." OncLive May 27, 2016 [4]
6. ↑ "Recurrent prostate cancer detection with anti-3-[(18)FFACBC PET/CT: comparison with CT"]. Eur. J. Nucl. Med. Mol. Imaging 43 (10): 1773–1783. 2016. doi:10.1007/s00259-016-3383-8. PMID 27091135.
7. ↑ "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. 2016. doi:10.1016/j.eururo.2016.01.029. PMID 26850970.
8. ↑ "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. 2015. doi:10.1097/RLU.0000000000000849. PMID 26053708.
9. ↑ Bankhead C. "Prostate Scan Agent Approved by FDA." MedPage Today May 27, 2016 [5]
10. ↑ 10.0 10.1 10.2 10.3 10.4 10.5 10.6 "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. 2014. doi:10.2967/jnumed.114.143628. PMID 25453047.
11. ↑ 11.0 11.1 11.2 "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. 2014. doi:10.1016/j.eururo.2013.08.053. PMID 24094575.

## External links

* "Fluciclovine". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/fluciclovine.

* v
* t
* e

Diagnostic radiopharmaceuticals (ATC: V09)

Central nervous system|

* 99mTc (Exametazime)
* 123I (Ioflupane
* Iofetamine
* Iomazenil)
* 18F (Florbetapir, Flutemetamol)

Skeletal system|

* 99mTc (Medronic acid)

Renal|

* 123I (Sodium iodohippurate)
* 64Cu (Cu-ETS2)

Gastrointestinal/Hepatic|

* 75Se (SeHCAT)

Respiratory system|

* 133Xe
* 81mKr
* 99mTc (99mTc-MAA)

Cardiovascular system|

* 99mTc (Sestamibi
* Tetrofosmin)
* 111In (Imciromab)
* 82Rb (Rubidium chloride)

Inflammation/infection|

* 99mTc (Exametazime
* Sulesomab
* Tilmanocept)
* 111In
* 67Ga

Tumor|

* 99mTc (Arcitumomab
* Votumumab
* Hynic-octreotide)
* 111In (Capromab pendetide
* Satumomab pendetide)
* 125I (Minretumomab)
* 123I / 131I (Iobenguane)
* 18F (Fluciclovine
* Fludeoxyglucose
* Fluoroethyltyrosine
* Sodium fluoride)

Adrenal cortex|

* 123I
* 125I / 131I (Iodocholesterol)

Radionuclides
(including tracers)|

| positron (PET list)|

* 11C ([11C]ME@HAPTHI
* 25B-NBOMe (Cimbi-36)
* Acetate
* Choline
* Carfentanil
* DASB
* DTBZ
* Flumazenil
* Methionine
* N-Methylspiperone
* Pittsburgh compound B
* Raclopride
* Verapamil)
* 13N (Ammonia)
* 15O (Water)
* 18F (Altanserin
* Desmethoxyfallypride
* FMISO
* Fallypride
* Florbetaben
* Florbetapir
* Flubatine
* Fluciclovine
* Fludeoxyglucose (18F) (FDG)-glucose analogue
* Flumazenil
* Fluorocholine
* Fluorodeoxysorbitol (FDS)
* Fluorodopa
* Fluorothymidine F-18
* Fluspidine
* Flutemetamol
* MPPF
* Mefway
* Nifene
* N-Methylspiperone
* FET
* Setoperone)
* 64Cu
* 68Ga
* 82Rb (Rubidium chloride)

|

gamma ray/photon (SPECT/scintigraphy)|

* 51Cr
* 57Co
* 67Ga
* 75Se
* 81mKr
* 99mTc
* 111In
* 123I
* 125I
* 131I
* 133Xe
* 153Sm
* 201Tl

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