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    CAS 1191237-69-0

    BUILDING BLOCK

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Gs-441524, 1191237-69-0, Gs441524, Gs 441524, Evo984, (2r,3r,4s,5r)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile
    Molecular Formula
    C12H13N5O4
    Molecular Weight
    291.26  g/mol
    InChI Key
    BRDWIEOJOWJCLU-LTGWCKQJSA-N
    FDA UNII
    1BQK176DT6
    GS-441524 is an adenosine nucleotide analog antiviral, similar to [remdesivir]. This molecule was patented in 2009. In vitro studies of GS-441524 have determined it has a higher EC50 than remdesivir against a number of viruses, meaning GS-441524 is less potent. GS-441524 continues to be studied in the treatment of Feline Infectious Peritonitis Virus, a coronavirus that only infects cats.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile
    2.1.2 InChI
    InChI=1S/C12H13N5O4/c13-4-12(10(20)9(19)7(3-18)21-12)8-2-1-6-11(14)15-5-16-17(6)8/h1-2,5,7,9-10,18-20H,3H2,(H2,14,15,16)/t7-,9-,10-,12+/m1/s1
    2.1.3 InChI Key
    BRDWIEOJOWJCLU-LTGWCKQJSA-N
    2.1.4 Canonical SMILES
    C1=C2C(=NC=NN2C(=C1)C3(C(C(C(O3)CO)O)O)C#N)N
    2.1.5 Isomeric SMILES
    C1=C2C(=NC=NN2C(=C1)[C@]3([C@@H]([C@@H]([C@H](O3)CO)O)O)C#N)N
    2.2 Other Identifiers
    2.2.1 UNII
    1BQK176DT6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (13c3)-gs-441524

    2. (2r,3r,4s,5r)-2-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furancarbonitrile

    3. 13c3 Gs-441524

    4. 13c3-gs-441524

    5. 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-d-altrononitrile

    6. Gs 441524

    7. Gs-441285

    8. Gs-441524

    9. Gs-828840

    10. Gs441524

    2.3.2 Depositor-Supplied Synonyms

    1. Gs-441524

    2. 1191237-69-0

    3. Gs441524

    4. Gs 441524

    5. Evo984

    6. (2r,3r,4s,5r)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile

    7. Evo-984

    8. 1bqk176dt6

    9. Evo 984

    10. 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-d-altrononitrile

    11. 2-c-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-d-altrononitrile

    12. D-altrononitrile, 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-

    13. (2~{r},3~{r},4~{s},5~{r})-2-(4-azanylpyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolane-2-carbonitrile

    14. Reacted Form

    15. Mfcd32666994

    16. (2r,3r,4s,5r)-2-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile

    17. U08

    18. Unii-1bqk176dt6

    19. Chembl2016757

    20. Schembl10120689

    21. Gtpl11445

    22. Chebi:147281

    23. Dtxsid201028047

    24. Ex-a3056

    25. Remdesivir Metabolite(gs-441524)

    26. Bdbm50571531

    27. S6814

    28. Zb1788

    29. Gs 441524 [who-dd]

    30. Akos037648588

    31. Remdesivir Intermediate(gs-441524)

    32. Bcp29949-1

    33. (2r,3r,4s,5r)-2-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furancarbonitrile

    34. Ac-31365

    35. Bs-14744

    36. Hy-103586

    37. Cs-0028160

    38. C22275

    39. D78523

    40. A933921

    41. (2r,3r,4s,5r)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

    2.4 Create Date
    2009-11-30
    3 Chemical and Physical Properties
    Molecular Weight 291.26 g/mol
    Molecular Formula C12H13N5O4
    XLogP3-1.4
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count2
    Exact Mass291.09675391 g/mol
    Monoisotopic Mass291.09675391 g/mol
    Topological Polar Surface Area150 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity456
    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 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.)

    4.2 Absorption, Distribution and Excretion

    Absorption

    GS-441524 has been found to transport poorly into cells compared to remdesivir.

    4.3 Metabolism/Metabolites

    GS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate.

    4.4 Mechanism of Action

    GS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate, which is incorporated into the genome of virions, terminating its replication.