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    Galidesivir

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 249503-25-1, Immucillin a, Immucillin-a, Bcx4430, Bcx-4430, Bcx 4430 free base
    Molecular Formula
    C11H15N5O3
    Molecular Weight
    265.27  g/mol
    InChI Key
    AMFDITJFBUXZQN-KUBHLMPHSA-N
    FDA UNII
    OLF97F86A7
    Galidesivir is an adenosine analog and RNA polymerase inhibitor, with potential broad-spectrum antiviral activity. Upon administration, galidesivir is metabolized to its monophosphate form, which is then converted into the active triphosphate nucleotide. Galidesivir triphosphate binds to viral RNA-dependent RNA polymerase (RdRp) and gets incorporated into the growing viral RNA strand, which leads to premature chain termination. This prevents viral transcription and replication.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3S,4R,5R)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
    2.1.2 InChI
    InChI=1S/C11H15N5O3/c12-11-8-6(14-3-15-11)4(1-13-8)7-10(19)9(18)5(2-17)16-7/h1,3,5,7,9-10,13,16-19H,2H2,(H2,12,14,15)/t5-,7+,9-,10+/m1/s1
    2.1.3 InChI Key
    AMFDITJFBUXZQN-KUBHLMPHSA-N
    2.1.4 Canonical SMILES
    C1=C(C2=C(N1)C(=NC=N2)N)C3C(C(C(N3)CO)O)O
    2.1.5 Isomeric SMILES
    C1=C(C2=C(N1)C(=NC=N2)N)[C@H]3[C@@H]([C@@H]([C@H](N3)CO)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    OLF97F86A7
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(4-amino-5h-pyrrolo(3,2-d)pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

    2. Bcx-4430

    3. Bcx4430

    4. Imma Cpd

    5. Immucillin A

    6. Immucillin-a

    2.3.2 Depositor-Supplied Synonyms

    1. 249503-25-1

    2. Immucillin A

    3. Immucillin-a

    4. Bcx4430

    5. Bcx-4430

    6. Bcx 4430 Free Base

    7. (2s,3s,4r,5r)-2-(4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

    8. Olf97f86a7

    9. Bcx4430 Freebase

    10. Imma Cpd

    11. 3,4-pyrrolidinediol,2-(4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)-2s,3s,4r,5r

    12. Bcx4430 (freebase)

    13. Unii-olf97f86a7

    14. (2s,3s,4r,5r)-2-{4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl}-5-(hydroxymethyl)pyrrolidine-3,4-diol

    15. Ua2

    16. Bcx4430freebase

    17. Galidesivir [inn]

    18. Galidesivir [who-dd]

    19. Chembl1236524

    20. Schembl12468816

    21. Gtpl11920

    22. Ex-a6295

    23. Bdbm50513995

    24. Hy-18649a

    25. Zinc13492903

    26. Cs-3779

    27. Db11676

    28. Ncgc00485882-01

    29. Bcx-4430 Freebase;immucillin-a;galidesivir

    30. P14655

    31. A900809

    32. (1s)-1-(9-carbaadenine-9-yl)-1,4-dideoxy-1,4-imino-d-ribitol

    33. 3,4-pyrrolidinediol, 2-(4-amino-5h-pyrrolo(3,2-d)pyrimidin-7-yl)-5-(hydroxymethyl)-, (2s,3s,4r,5r)-

    34. Galidesivir; Bcx4430; Bcx 4430; Bcx-4430;(2s,3s,4r,5r)-2-(4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 265.27 g/mol
    Molecular Formula C11H15N5O3
    XLogP3-2.1
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass265.11748936 g/mol
    Monoisotopic Mass265.11748936 g/mol
    Topological Polar Surface Area140 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity334
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Pharmacology

    Galidesivir is an adenosine analogue with a broad-spectrum antiviral activity against RNA viruses, including flaviviruses, togaviruses, bunyaviruses, arenaviruses, paramyxoviruses, coronaviruses, filoviruses, orthomyxoviruses, and picornaviruses.

    4.2 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.)

    4.3 Mechanism of Action

    Galidesivir works by binding to viral RNA polymerase where the natural nucleotide would bind, leading to the structural change in the viral enzyme due to altered electrostatic interactions. Disruption of viral RNA polymerase activity results in premature termination of the elongating RNA strand.