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2D Structure
Also known as: 18f-flt, Alovudine f-18, 3'-deoxy-3'-(18f)fluorothymidine, (18f)flt, Flt f-18, 287114-80-1
Molecular Formula
C10H13FN2O4
Molecular Weight
243.22  g/mol
InChI Key
UXCAQJAQSWSNPQ-ZIVQXEJRSA-N
FDA UNII
2X1K91UT6N

Fluorothymidine F-18 is a radioconjugate consisting of a thymidine analogue radiolabeled with fluorine F 18, a positron emitting isotope. Phosphorylated by S-phase-specific thymidine kinase 1, 3'-deoxy-3'-[18F]fluorothymidine (18F-FLT) is trapped intracellularly by entering the salvage pathway of DNA synthesis without incorporation into DNA. 18F-FLT serves a marker of tumor cell proliferation for imaging with positron emission tomography (PET); as a marker of proliferation rather than metabolism, it is more specific to tumor tissue than 2-deoxy-2-[18F] fluoro-D-glucose (18F-FDG). This agent is metabolically stable, accumulates in the normal bone marrow and the liver, and does not cross the blood-brain barrier.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[(2R,4S,5R)-4-(18F)fluoranyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
2.1.2 InChI
InChI=1S/C10H13FN2O4/c1-5-3-13(10(16)12-9(5)15)8-2-6(11)7(4-14)17-8/h3,6-8,14H,2,4H2,1H3,(H,12,15,16)/t6-,7+,8+/m0/s1/i11-1
2.1.3 InChI Key
UXCAQJAQSWSNPQ-ZIVQXEJRSA-N
2.1.4 Canonical SMILES
CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)F
2.1.5 Isomeric SMILES
CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)[18F]
2.2 Other Identifiers
2.2.1 UNII
2X1K91UT6N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (18)flt Cpd

2. (18f)3'-deoxy-3'-fluorothymidine

3. (18f)flt

4. 1-(3'-fluoro-3'-deoxy-beta-d-erythropentofuranosyl)thymine

5. 18f-flt

6. 3'-(f-18)fluoro-3'-deoxythymidine

7. 3'-deoxy-3'-(18f)fluorothymidine

8. 3'-deoxy-3'-fluorothymidine

9. 3'-fluoro-2',3'-dideoxythymidine

10. 3'-fluoro-3'-deoxythymidine

11. 3'-fluorothymidine

12. Alovudine

13. Fddt

2.3.2 Depositor-Supplied Synonyms

1. 18f-flt

2. Alovudine F-18

3. 3'-deoxy-3'-(18f)fluorothymidine

4. (18f)flt

5. Flt F-18

6. 287114-80-1

7. Thymidine, 3'-deoxy-3'-(18f)fluoro-

8. 2x1k91ut6n

9. [18f]flt

10. F-18 Fluorothymidine

11. Unii-2x1k91ut6n

12. 3'-deoxy-3'-18f-fluorothymidine

13. Schembl14461296

14. (18f) Flt

15. (18f)-flt

16. (f-18)flt

17. Dtxsid90182869

18. Db14930

19. Fluorothymidine (18f) [who-dd]

20. Q27255730

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 243.22 g/mol
Molecular Formula C10H13FN2O4
XLogP3-0.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass243.088469 g/mol
Monoisotopic Mass243.088469 g/mol
Topological Polar Surface Area78.9 Ų
Heavy Atom Count17
Formal Charge0
Complexity385
Isotope Atom Count1
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)