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Fluorothymidine F-18

Fluorothymidine F-18

Synopsis, Chemistry

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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

Fluorothymidine F-18

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 Formula	C₁₀H₁₃FN₂O₄
Molecular Weight	243.22 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	243.088469 g/mol
Monoisotopic Mass	243.088469 g/mol
Topological Polar Surface Area	78.9 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	385
Isotope Atom Count	1
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)