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UNII-38R1Q0L1ZE

UNII-38R1Q0L1ZE

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Also known as: Fluciclovine f-18, Axumin, 222727-39-1, Fluciclovine f 18, Facbc, Fluciclovine f18

Molecular Formula

C₅H₈FNO₂

Molecular Weight

132.12 g/mol

InChI Key

NTEDWGYJNHZKQW-KWCOIAHCSA-N

FDA UNII

38R1Q0L1ZE

Fluciclovine F18 is a radiotracer containing a synthetic amino acid analogue of L-leucine radiolabeled with fluorine F 18 with potential diagnostic imaging use. Similar to most amino acids, fluciclovine F18 appears to enter cells through the energy-independent L-type amino acid transporter (LAT) system. As an amino acid analogue, this agent is preferentially accumulated by tumor cells due to their increased metabolic needs; however, unlike naturally occurring amino acids, this non-natural amino acid-analogue radiotracer is not metabolized. Accordingly, fluciclovine F18 accumulates in tumor cells and can potentially be used to image tumors using positron emission tomography (PET).

Fluciclovine f-18 is a Radioactive Diagnostic Agent. The mechanism of action of fluciclovine f-18 is as a Positron Emitting Activity.

1 2D Structure

UNII-38R1Q0L1ZE

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-amino-3-(18F)fluoranylcyclobutane-1-carboxylic acid

2.1.2 InChI

InChI=1S/C5H8FNO2/c6-3-1-5(7,2-3)4(8)9/h3H,1-2,7H2,(H,8,9)/i6-1

2.1.3 InChI Key

NTEDWGYJNHZKQW-KWCOIAHCSA-N

2.1.4 Canonical SMILES

C1C(CC1(C(=O)O)N)F

2.1.5 Isomeric SMILES

C1C(CC1(C(=O)O)N)[18F]

2.2 Other Identifiers

2.2.1 UNII

38R1Q0L1ZE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (18f)ge-148

2. (1r,3r)-1-amino-3(18f)fluorocyclobutane-1-carboxylic Acid

3. 1-amino-3-fluorocyclobutane-1-carboxylic Acid

4. Anti-(18f)facbc

5. Axumin

6. Cyclobutanecarboxylic Acid, 1-amino-3-(fluoro-18f)-, Trans-

7. F(18)-facbc

8. F(18)1-amino-3-fluorocyclobutane-1-carboxylic Acid

9. F-facbc

10. Fluciclovine F 18

11. Fluciclovine F-18

12. Ge-148 (18f)

13. Ge-148 F-18

14. Nmk 36

15. Nmk-36

16. Nmk36 Cpd

2.3.2 Depositor-Supplied Synonyms

1. Fluciclovine F-18

2. Axumin

3. 222727-39-1

4. Fluciclovine F 18

5. Facbc

6. Fluciclovine F18

7. Nmk36

8. Ge-148

9. (18f)fluciclovine

10. Fluciclovine (18f) [inn]

11. Nmk-36

12. (18f)ge-148

13. Ge-148 F-18

14. Ge-148 (18f)

15. (18f)facbc

16. Facbc F-18

17. 38r1q0l1ze

18. Anti-1-amino-3-(18f)fluorocyclobutane-1-carboxylic Acid

19. (1r,3r)-1-amino-3(18f)fluorocyclobutane-1-carboxylic Acid

20. [18f]fluciclovine

21. [18f]facbc

22. Fluciclovine (18f) (inn)

23. 1-amino-3-(18f)fluoranylcyclobutane-1-carboxylic Acid

24. Cyclobutanecarboxylic Acid, 1-amino-3-(fluoro-18f)-, Trans-

25. Anti-(18f)fabc

26. Fluciclovine F18 [usan]

27. Anti-1-amino-3-[18f]fluorocyclobutane-1-carboxylic Acid

28. Unii-38r1q0l1ze

29. Fluciclovine ((sup 18)f)

30. Fluciclovine-f18

31. Moli001120

32. Fluciclovine ((sup 18)f) [inn]

33. Axumin (tn)

34. Nmk36 Cpd

35. Anti-[18f]facbc

36. Syn-3-[18f]facbc

37. Fluciclovine F-18 (usan)

38. Chembl254468

39. Chembl447701

40. Nmk 36

41. Schembl10017245

42. Schembl11939897

43. Schembl11939900

44. Chebi:134703

45. Dtxsid601027796

46. Fluciclovine (18f) [mi]

47. Fluciclovine F 18 [usan]

48. Bcp24384

49. Axumincn Facbccn Fluciclovine (18f)cn Ge 148cn Nmk 36

50. At31246

51. Db13146

52. Fluciclovine (18f) [who-dd]

53. Fluciclovine F-18 [orange Book]

54. D10860

55. F(18)1-amino-3-fluorocyclobutane-1-carboxylic Acid

56. Q25313613

57. Syn-1-amino-3-[18f]fluorocyclobutane-1-carboxylic Acid

58. Anti-3[18f] Facbc;f18; Anti-1-amino-3-18f-fluorocyclobutane-1-carboxylic Acid (facbc)

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₅H₈FNO₂
Molecular Weight	132.12 g/mol
XLogP3	-2.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	132.056441 g/mol
Monoisotopic Mass	132.056441 g/mol
Topological Polar Surface Area	63.3 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	142
Isotope Atom Count	1
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Fluciclovine is indicated as a detection agent for positron emission tomography (PET) in men with suspected prostate cancer recurrence based on elevated blood prostate specific antigen (PSA) levels following prior treatment. The overexpression of L-type amino acid transporters such as LAT1 and LAT3 that mediate the uptake of essential amino acids has been extensively reported as a tumoral mechanism of cell growth.

FDA Label

This medicinal product is for diagnostic use only.

Axumin is indicated for Positron Emission Tomography (PET) imaging to detect recurrence of prostate cancer in adult men with a suspected recurrence based on elevated blood prostate specific antigen (PSA) levels after primary curative treatment.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Following intravenous administration, the tumor-to-normal tissue contrast is highest between 2 and 10 minutes after injection, with a 63% reduction in mean tumor uptake at 90 minutes after injection. The scanning time point should be evaluated carefully as an early scanning can present an increased blood pool and a late scanning will translate into an increased muscle uptake. These variations should always be considered in the image interpretation.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

FLUCICLOVINE F-18

5.2.2 FDA UNII

38R1Q0L1ZE

5.2.3 Pharmacological Classes

Radioactive Diagnostic Agent [EPC]; Positron Emitting Activity [MoA]

5.3 ATC Code

V09IX12

V - Various

V09 - Diagnostic radiopharmaceuticals

V09I - Tumour detection

V09IX - Other diagnostic radiopharmaceuticals for tumour detection

V09IX12 - Fluciclovine (18F)

5.4 Absorption, Distribution and Excretion

Absorption

After intravenous administration of fluciclovine, the major distribution happens in liver (14%), red bone marrow (12%), lung (7%), myocardium (4%) and pancreas (3%). With increasing time, the dose gets distributed into skeletal muscle.

Route of Elimination

In the first four hours post-injection, 3% of administered dose is excreted in the urine which increases to 5% after 24 hours post-injection.

Volume of Distribution

The compartmental volume of distribution of fluciclovine is in prostate 0.97 L, vesicle 0.79 L, red bone marrow 0.98 L, gluteus muscle 2.13 L and obturator muscle 2.23 L.

Clearance

Fluciclovine renal clearance and excretion is minimal.

5.5 Metabolism/Metabolites

Fluciclovine is not metabolized and it is not incorporated into newly synthesized proteins.

5.6 Biological Half-Life

Fluciclovine is a cyclotron produced radionuclide that decays by positron emission (+ decay, 96.7%) and orbital electron capture (3.3%) to stable oxygen 18 with a physical half-life of 109.7 minutes.

5.7 Mechanism of Action

Fluciclovine is transported into the prostate cancer cells via ASCT2 and LAT1 transporters. The activity of LAT1 gets increased in acidic pH, condition that is developed intra-tumorally at certain size. The uptake of fluciclovine presents an androgen-dependent dynamic in hormone sensitive cells.