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    Resiquimod
    Also known as: 144875-48-9, R-848, 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol, 1-[4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol, Resiquimod [inn], R 848
    Molecular Formula
    C17H22N4O2
    Molecular Weight
    314.4  g/mol
    InChI Key
    BXNMTOQRYBFHNZ-UHFFFAOYSA-N
    FDA UNII
    V3DMU7PVXF
    Resiquimod is an imidazoquinolinamine and Toll-like receptor (TLR) agonist with potential immune response modifying activity. Resiquimod exerts its effect through the TLR signaling pathway by binding to and activating TLR7 and 8 mainly on dendritic cells, macrophages, and B-lymphocytes. This induces the nuclear translocation of the transcription activator NF-kB as well as activation of other transcription factors. This may lead to an increase in mRNA levels and subsequent production of cytokines, especially interferon-alpha (INF-a) and other cytokines, thereby enhancing T-helper 1 (Th1) immune responses. In addition, topical application of resiquimod appears to activate Langerhans' cells, leading to an enhanced activation of T-lymphocytes. Due to its immunostimulatory activity, this agent may potentially be useful as a vaccine adjuvant.
    1 2D Structure

    Resiquimod

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
    2.1.2 InChI
    InChI=1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)
    2.1.3 InChI Key
    BXNMTOQRYBFHNZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N
    2.2 Other Identifiers
    2.2.1 UNII
    V3DMU7PVXF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. R 848

    2. R-848

    3. R848 Compound

    2.3.2 Depositor-Supplied Synonyms

    1. 144875-48-9

    2. R-848

    3. 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

    4. 1-[4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

    5. Resiquimod [inn]

    6. R 848

    7. Resiquimod (r-848)

    8. R848

    9. S 28463

    10. S-28463

    11. V3dmu7pvxf

    12. Mfcd00937759

    13. Chembl383322

    14. Chebi:36706

    15. 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

    16. Cd11301

    17. Cd-11301

    18. R848;s28463

    19. 2252319-44-9

    20. 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

    21. 1h-imidazo[4,5-c]quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-

    22. 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol

    23. R848 Compound

    24. Unii-v3dmu7pvxf

    25. 1h-imidazo(4,5-c)quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-

    26. 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1h-imidazo(4,5-c)quinoline-1-ethanol

    27. Resiquimodr848

    28. Vml-600

    29. Rx8

    30. R848; Resiquimod

    31. S28463

    32. Resiquimod [mi]

    33. Resiquimod [usan]

    34. Resiquimod [mart.]

    35. Resiquimod [who-dd]

    36. Schembl34159

    37. Mls006010212

    38. Alpha-dimethyl-1h-imidazo(4,5-c)quinoline-1-ethanol

    39. Gtpl5051

    40. Dtxsid7040603

    41. Resiquimod, >=98% (hplc)

    42. Hms3740o09

    43. Bcp09103

    44. Ex-a1879

    45. Bdbm50241029

    46. S8133

    47. Zinc28572103

    48. Akos016003509

    49. Ccg-267635

    50. Cs-1706

    51. Db06530

    52. Sb17111

    53. 1-(4-amino-2-ethoxymethyl-imidazo[4,5-c]quinolin-1-yl)-2-methyl-propan-2-ol

    54. Ncgc00370784-01

    55. Ncgc00370784-05

    56. Ac-35716

    57. As-30885

    58. Hy-13740

    59. Smr002530531

    60. Sy107476

    61. Ft-0763049

    62. R0197

    63. Resiquimod, Vml-600, R-848, S-28463

    64. A856222

    65. Q426054

    66. Sr-01000944954

    67. J-008020

    68. Sr-01000944954-1

    69. 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methyl-propan-2-ol

    70. 4-amino-2-ethoxymethyl-alpha,alpha-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol

    71. 4-amino-alpha,alpha-dimethyl-2-ethoxymethyl-1h-imidazo[4,5-c]quinolin-1-ethanol

    72. 4-amino-alpha,alpha-dimethyl-2-ethoxymethyl-1h-imidazo[4,5-c]quinoline-1-ethanol

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 314.4 g/mol
    Molecular Formula C17H22N4O2
    XLogP31.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass314.17427596 g/mol
    Monoisotopic Mass314.17427596 g/mol
    Topological Polar Surface Area86.2 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity406
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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 genital herpes.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    Resiquimod is a Toll-like receptor 7 (TLR7) and TLR8 agonist that is a potent inducer of alpha interferon (IFN-alpha) and other cytokines.

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