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Clevudine

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Synopsis

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Chemistry

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Also known as: Clevudine, 163252-36-6, L-fmau, Levovir, Clevudine (levovir), In51mvp5f1

Molecular Formula

C₁₀H₁₃FN₂O₅

Molecular Weight

260.22 g/mol

InChI Key

GBBJCSTXCAQSSJ-XQXXSGGOSA-N

FDA UNII

IN51MVP5F1

Clevudine is a synthetic pyrimidine analogue with activity against hepatitis B virus (HBV). Intracellularly, clevudine is phosphorylated to its active metabolites, clevudine monophosphate and triphosphate. The triphosphate metabolite competes with thymidine for incorporation into viral DNA, thereby causing DNA chain termination and inhibiting the function of HBV DNA polymerase (reverse transcriptase). Clevudine has a long half-life and shows significant reduction of covalently closed circular DNA (cccDNA), therefore the patient is less likely to have a relapse after treatment is discontinued.

1 2D Structure

Clevudine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

2.1.2 InChI

InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1

2.1.3 InChI Key

GBBJCSTXCAQSSJ-XQXXSGGOSA-N

2.1.4 Canonical SMILES

CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)F

2.1.5 Isomeric SMILES

CC1=CN(C(=O)NC1=O)[C@@H]2[C@@H]([C@H]([C@@H](O2)CO)O)F

2.2 Other Identifiers

2.2.1 UNII

IN51MVP5F1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-methyl-2,4(1h,3h)-pyrimidinedione,

2. 1-(2-deoxy-2-fluoro-beta-l-arabinofuranosyl)-5-methyl-2,4(1h,3h)-pyrimidinedione

3. 1-(2-fluoro-2-deoxy-beta-arabinofuranosyl)thymine

4. 1-(2-fluoro-2-deoxy-beta-d-arabinofuranosyl)thymine

5. 1-(2-fluoro-5-methyl-beta,l-arabinofuranosyl)uracil

6. 1-(2-fluoro-beta-l-arabinofuranosyl)thymine

7. 2'-deoxy-2'-fluoroarabinofuranosylthymine

8. 2'-fluoro-5-methyl-1-beta-d-arabinofuranosyluracil

9. 2'-fluoro-5-methylarabinosyluracil

10. 2'-fluoro-5-methylarabinosyluracil, 2-(14)c-labeled

11. 5-methyl-2'-fluoroarauracil

12. Clevudine

13. D-fmau

14. Fmau

15. L-fmau

2.3.2 Depositor-Supplied Synonyms

1. Clevudine

2. 163252-36-6

3. L-fmau

4. Levovir

5. Clevudine (levovir)

6. In51mvp5f1

7. 1-(2-deoxy-2-fluoro-beta-l-arabinofuranosyl)thymine

8. 2'-fluoro-5-methyl-beta-l-arabinofuranosyluracil

9. Clevudine (usan)

10. Clevudine [usan]

11. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-.beta.-l-arabinofuranosyl)-5-methyl-

12. Clevudine [usan:inn]

13. Unii-in51mvp5f1

14. Revovir

15. Mfcd00935785

16. Clevudine (form 2)

17. 1-(2-deoxy-2-fluoro-ss-l-arabinofuranosyl)-5-methyl-2,4-(1h,3h)-pyrimidinedione

18. Clevudine [inn]

19. Clevudine [mi]

20. Clevudine [who-dd]

21. 1-[(2s,3r,4s,5s)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

22. Mls006011168

23. Schembl233494

24. Chembl458875

25. Zinc1484

26. Dtxsid2057659

27. Chebi:135964

28. S3001

29. Akos015951181

30. Ac-1177

31. Ccg-267053

32. Db06683

33. Ds-3428

34. 1-(2-deoxy-2-fluoro-beta-l-arabinofuranosyl)-5-methyl-2,4(1h,3h)-pyrimidinedione

35. Ncgc00371259-05

36. 1-[(2s,3r,4s,5s)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

37. Am807730

38. Smr004702937

39. D03537

40. A855725

41. 2'-fluoro-5-methyl-.beta.-l-arabinofuranosyluracil

42. Q1100864

43. 1-(2-deoxy-2-fluoro-beta-l-arabinofuranosyl) Thymine

44. 1-(2-deoxy-2-fluoro-.beta.-l-arabinofuranosyl)thymine

45. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-

46. A-l-arabinofuranosyl)-5-methyl-

47. 1-[(2s,3r,4s,5s)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-5-methyl-pyrimidin-2-one

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₃FN₂O₅
Molecular Weight	260.22 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	260.08084968 g/mol
Monoisotopic Mass	260.08084968 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	413
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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

Investigated for use/treatment in hepatitis (viral, B).

5 Pharmacology and Biochemistry

5.1 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.)

5.2 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF12 - Clevudine

KDMF