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    Clevudine

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    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

    2D Structure

    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 Weight 260.22 g/mol
    Molecular Formula C10H13FN2O5
    XLogP3-0.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass260.08084968 g/mol
    Monoisotopic Mass260.08084968 g/mol
    Topological Polar Surface Area99.1 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity413
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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

    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