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Chemistry

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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
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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15-Dec-2023
28-Jun-2024
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