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    Elvucitabine

    INTERMEDIATES

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 181785-84-2, Beta-l-fd4c, L-fd4c, .beta.-l-fd4c, Ach-126,443, L-f-d4c
    Molecular Formula
    C9H10FN3O3
    Molecular Weight
    227.19  g/mol
    InChI Key
    HSBKFSPNDWWPSL-VDTYLAMSSA-N
    FDA UNII
    M09BUF90C0
    Elvucitabine is a nucleoside reverse transcriptase inhibitor analog of cytosine. Elvucitabine has activity against HIV and chronic hepatitis B.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one
    2.1.2 InChI
    InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1
    2.1.3 InChI Key
    HSBKFSPNDWWPSL-VDTYLAMSSA-N
    2.1.4 Canonical SMILES
    C1=CC(OC1CO)N2C=C(C(=NC2=O)N)F
    2.1.5 Isomeric SMILES
    C1=C[C@H](O[C@H]1CO)N2C=C(C(=NC2=O)N)F
    2.2 Other Identifiers
    2.2.1 UNII
    M09BUF90C0
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine

    2. 2',3'-dideoxy-2',3'-didehydro-beta-d-5-fluorocytidine

    3. 2',3'-dideoxy-2',3'-didehydro-beta-l-5-fluorocytidine

    4. 2(1h)-pyrimidinone, 4-amino-1-((2s,5r)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-

    5. 4-amino-5-fluoro-1-((2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one

    6. Ach-126-443

    7. Beta-d-d4fc

    8. Beta-l-fd4c

    9. D-d4fc

    10. Dexelvucitabine

    11. Dpc 817

    12. Dpc-817

    13. Dpc817

    14. Incb-8721

    15. L-d4fc

    16. Reverset

    2.3.2 Depositor-Supplied Synonyms

    1. 181785-84-2

    2. Beta-l-fd4c

    3. L-fd4c

    4. .beta.-l-fd4c

    5. Ach-126,443

    6. L-f-d4c

    7. Ach-126443

    8. L-d4fc

    9. 4-amino-5-fluoro-1-((2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one

    10. 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one

    11. M09buf90c0

    12. 2(1h)-pyrimidinone, 4-amino-1-((2s,5r)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-

    13. 2(1h)-pyrimidinone, 4-amino-1-[(2s,5r)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-fluoro-

    14. Elvucitabine [usan]

    15. Elvucitabine [usan:inn]

    16. Unii-m09buf90c0

    17. Ach 126443

    18. Ach 126,443

    19. B-l-fd4c

    20. Elvucitabine (usan/inn)

    21. Elvucitabine [inn]

    22. Chembl38700

    23. (-)fd4c

    24. Schembl1649928

    25. Zinc7048

    26. Beta-l-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine

    27. Dtxsid20171185

    28. Bdbm50421604

    29. Db06236

    30. Hy-117582

    31. Cs-0066557

    32. A14435

    33. D03981

    34. J-011630

    35. Q1334337

    36. .beta.-l-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

    37. 2(1h)-pyrimidinone, 4-amino-1-(2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-, (2s-cis)-

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 227.19 g/mol
    Molecular Formula C9H10FN3O3
    XLogP3-1.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass227.07061935 g/mol
    Monoisotopic Mass227.07061935 g/mol
    Topological Polar Surface Area88.2 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity405
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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) and HIV infection.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Reverse Transcriptase Inhibitors

    Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    5.2 Mechanism of Action

    Elvucitabine is a L-cytosine Nucleoside analog Reverse Transcriptase Inhibitor (NRTIs) anti-HIV drug. NRTI's inhibit the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). It is believed that inhibition of reverse transcriptase interferes with the generation of DNA copies of viral RNA, which, in turn, are necessary for synthesis of new virions. Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Thus, reverse transcriptase inhibitors are virustatic and do not eliminate HIV from the body.