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Fluorodopa F-18

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1 FDA Orange Book

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Synopsis

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Chemistry

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Also known as: Fluorodopa f 18, Fluorodopa f18, Fluorodopa f-18, 92812-82-3, 18f-dopa, L-6-(18f)fluoro-dopa

Molecular Formula

C₉H₁₀FNO₄

Molecular Weight

214.18 g/mol

InChI Key

PAXWQORCRCBOCU-RPDRGXCHSA-N

FDA UNII

2C598205QX

Fluorodopa F 18 is the amino acid analog fluorodopa (FDOPA) labeled with fluorine F 18, a positron-emitting isotope, with potential tumor tracer property. Fluorine F 18 fluorodopa is able to cross the blood-brain barrier and is taken up by brain tumor cells. As uptake is higher in tumor cells, tumors may then be imaged using positron emission tomography (PET). Assessing tumor uptake of FDOPA may be beneficial for diagnosis, localization and in determining further treatment.

1 2D Structure

Fluorodopa F 18

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-3-(2-(18F)fluoranyl-4,5-dihydroxyphenyl)propanoic acid

2.1.2 InChI

InChI=1S/C9H10FNO4/c10-5-3-8(13)7(12)2-4(5)1-6(11)9(14)15/h2-3,6,12-13H,1,11H2,(H,14,15)/t6-/m0/s1/i10-1

2.1.3 InChI Key

PAXWQORCRCBOCU-RPDRGXCHSA-N

2.1.4 Canonical SMILES

C1=C(C(=CC(=C1O)O)F)CC(C(=O)O)N

2.1.5 Isomeric SMILES

C1=C(C(=CC(=C1O)O)[18F])C[C@@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

2C598205QX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (18)f-dopa

2. 18f-fdopa

3. 2-fluoro-5-hydroxytyrosine

4. 3,4-dihydroxy-6-fluorophenylalanine

5. 3-(2-fluoro-(18)f-4,5-dihydroxyphenyl)-l-alanine

6. 6-(18f)fluoro-l-3,4-dihydroxyphenylalanine

7. 6-(18f)fluoro-l-dopa

8. 6-fluoro-dopa

9. 6-fluorodopa

10. Fluorodopa

11. Fluorodopa F 18

12. Fluorodopa F 18, (18)f-labeled Cpd

13. Fluorodopa F-18

2.3.2 Depositor-Supplied Synonyms

1. Fluorodopa F 18

2. Fluorodopa F18

3. Fluorodopa F-18

4. 92812-82-3

5. 18f-dopa

6. L-6-(18f)fluoro-dopa

7. Fluorine-18-fluoro-l-dopa

8. 18f-l-fluoro-dopa

9. Fdopa F-18

10. Fluorodopa (18f) [inn]

11. Chebi:49166

12. 2c598205qx

13. L-tyrosine, 2-(fluoro-18f)-5-hydroxy-

14. (s)-2-amino-3-(2-(fluoro-18f)-4,5-dihydroxyphenyl)propanoic Acid

15. Fluorodopa F 18 (usan)

16. Fluorodopa F 18 [usan]

17. F-dopa

18. (18f)fdopa

19. 6-(18f)fluoro-l-dopa

20. 2-(fluoro-18f)-l-dopa

21. Unii-2c598205qx

22. Fluorodopa-f-18

23. Fluorodopa F 18 [usan:usp:inn]

24. 2-(fluoro-18f)-5-hydroxy-l-tyrosine

25. Fluorodopa ((18)f)

26. Fluorodopa F18 (tn)

27. Schembl522323

28. Fluorodopa F18 [mi]

29. ((18)f)fdopa

30. 6-((18)f)fluoro-l-dopa

31. Chembl3400972

32. L-6-((18)f)fluoro-dopa

33. Dtxsid60239157

34. Moli000246

35. Moli000965

36. Fluorodopa (18f) [who-dd]

37. Db13848

38. Fluorodopa F-18 [orange Book]

39. 18f-fluoro-dihydroxyphenylalanine

40. Fluorodopa F 18 [usp Impurity]

41. 2-((18)f)fluoro-5-hydroxy-l-tyrosine

42. 2-(fluoro-(18)f)-5-hydroxy-l-tyrosine

43. D04220

44. L-tyrosine, 2-(fluoro-(sup 18)f)-5-hydroxy-

45. 6-((18)f)fluoro-3,4-dihydroxy-l-phenylalanine

46. L-3,4-dihydroxy-6-(18f)fluorophenylalanine

47. 3-(2-fluoro-(18)f-4,5-dihydroxyphenyl)-l-alanine

48. 6-fluoro-(18f)-l-3,4-dihydroxyphenylalanine

49. Q27121509

50. (18f)-6-fluoro-l,3,4, Dihydroxyphenylalanine

51. 3-(2-fluoro-(sup 18)f-4,5-dihydroxyphenyl)-l-alanine

52. (2s)-2-amino-3-(2-(18f)fluoranyl-4,5-dihydroxyphenyl)propanoic Acid

53. (2s)-2-amino-3-[2-((18)f)fluoro-4,5-dihydroxyphenyl]propanoic Acid

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀FNO₄
Molecular Weight	214.18 g/mol
XLogP3	-2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	214.061920 g/mol
Monoisotopic Mass	214.061920 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	238
Isotope Atom Count	1
Defined Atom Stereocenter Count	1
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

Fluorodopa F 18 is indicated for use with positron emission tomography (PET) to visualize dopaminergic nerve terminals in the striatum for the evaluation of adult patients with suspected Parkinsonian syndromes (PS).

5 Pharmacology and Biochemistry

5.1 ATC Code

V - Various

V09 - Diagnostic radiopharmaceuticals

V09I - Tumour detection

V09IX - Other diagnostic radiopharmaceuticals for tumour detection

V09IX05 - Fluorodopa (18F)

5.2 Absorption, Distribution and Excretion

Route of Elimination

Approximately 80% of the administered radioactivity is eliminated in the urine.

Clearance

The agent is cleared from blood and tissue within 24 hours following administration.

5.3 Metabolism/Metabolites

Fluorodopa F 18 is decarboxylated by aromatic amino acid decarboxylase (AADC) in the striatum to fluorodopamine F 18. Fluorodopamine F 18 is then further metabolized by monoamine oxidase (MAO) to yield [18F] 6-fluoro-3,4-dihydroxyphenylacetic acid, then subsequently by COMT to yield [18F]6-fluorohomovanillic acid.

5.4 Biological Half-Life

The plasma half-life following intravenous administration is approximately 1-3 hours.

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