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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
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 Weight 214.18 g/mol
Molecular Formula C9H10FNO4
XLogP3-2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass214.061920 g/mol
Monoisotopic Mass214.061920 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count15
Formal Charge0
Complexity238
Isotope Atom Count1
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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