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    ABX464

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    DIGITAL CONTENT

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    2D Structure
    Also known as: Abx-464, Abx464, Obefazimod, 1258453-75-6, Spl-464, Obefazimod [usan]
    Molecular Formula
    C16H10ClF3N2O
    Molecular Weight
    338.71  g/mol
    InChI Key
    OZOGDCZJYVSUBR-UHFFFAOYSA-N
    FDA UNII
    26RU378B9V
    Obefazimod is an orally available, small molecule binder of the cap binding complex (CBC) 80/20, with potential antiviral and anti-inflammatory activities. Upon oral administration, obefazimod binds to the CBC, a complex at the 5'-end of the pre-mRNA transcript that promotes the initial interaction with transcription and processing machinery. This leads to a conformational change in the CBC and enhanced splicing of viral RNA variants and upregulation of the anti-inflammatory microRNA, miR-124, via splicing of a long noncoding RNA at the miR-124-1 locus. In human immunodeficiency virus type 1 (HIV-1)-infected cells, obefazimod interacts with the CBC of HIV-1 mRNA and inhibits viral replication by preventing Rev-mediated export of unspliced HIV-1 transcripts to the cytoplasm. Rev facilitates the nuclear export of unspliced or incompletely spliced viral pre-mRNAs, an essential step in HIV-1 replication. In inflammatory conditions, miR-124 reduces the production of various inflammatory mediators, including interleukin 6 (IL-6), tumor necrosis factor alpha (TNF-alpha), and C-C motif chemokine 2 (CCL2; MCP-1.). miR-124 plays a critical role in innate and adaptive immune responses and is a critical mediator of cholinergic anti-inflammatory action.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    8-chloro-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine
    2.1.2 InChI
    InChI=1S/C16H10ClF3N2O/c17-13-3-1-2-10-4-9-14(22-15(10)13)21-11-5-7-12(8-6-11)23-16(18,19)20/h1-9H,(H,21,22)
    2.1.3 InChI Key
    OZOGDCZJYVSUBR-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC2=C(C(=C1)Cl)N=C(C=C2)NC3=CC=C(C=C3)OC(F)(F)F
    2.2 Other Identifiers
    2.2.1 UNII
    26RU378B9V
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Abx464

    2.3.2 Depositor-Supplied Synonyms

    1. Abx-464

    2. Abx464

    3. Obefazimod

    4. 1258453-75-6

    5. Spl-464

    6. Obefazimod [usan]

    7. 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine

    8. 26ru378b9v

    9. 2-quinolinamine, 8-chloro-n-(4-(trifluoromethoxy)phenyl)-

    10. Obefazimod [inn]

    11. Unii-26ru378b9v

    12. Schembl1705888

    13. Abx-464 [who-dd]

    14. Chembl4297344

    15. Gtpl11698

    16. Ex-a3322

    17. Who 12112

    18. Db14828

    19. Mmv1581032

    20. Sb18690

    21. Ac-35811

    22. Bs-14770

    23. Abx464(abx-464;abx 464)

    24. Hy-100870

    25. Cs-0020537

    26. S0076

    27. A16912

    28. D84095

    29. Q27896117

    2.4 Create Date
    2011-01-31
    3 Chemical and Physical Properties
    Molecular Weight 338.71 g/mol
    Molecular Formula C16H10ClF3N2O
    XLogP35.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass338.0433751 g/mol
    Monoisotopic Mass338.0433751 g/mol
    Topological Polar Surface Area34.2 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity388
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1