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Resiquimod

Resiquimod structure

Resiquimod 

structure
  • CAS No:

    144875-48-9

  • Formula:

    C17H22N4O2

  • Chemical Name:

    Resiquimod

  • Synonyms:

    1H-Imidazo[4,5-c]quinoline-1-ethanol,4-amino-2-(ethoxymethyl)-α,α-dimethyl-;4-Amino-2-(ethoxymethyl)-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol;S 28463;R 848;Resiquimod;1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol;Resimiquimod;4-Amino-2-(ethoxymethyl)-1-(2-hydroxyisobutyl)imidazo[4,5-c]quinoline;1-[4-Amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol;171742-32-8;208711-44-8

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

Resiquimod is an imidazoquinoline.|A substance being studied in the treatment of some types of skin cancer. When put on the skin, resiquimod causes some immune cells to make certain chemicals that may help them kill tumor cells. It is also being studied to find out if adding it to a tumor vaccine improves the antitumor immune response. It is a type of imidazoquinoline and a type of immunomodulator.|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.

Resiquimod Basic Attributes

314.38200

314.38

V3DMU7PVXF

DTXSID7040603

C63958

2933990090

Characteristics

86.19000

3.05530

1.28g/cm3

553.6ºC at 760mmHg

288.6ºC

1.634

4.33E-13mmHg at 25°C

Safety Information

|Danger|H228 (100%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

Investigated for use/treatment in genital herpes.

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

R 848

Resiquimod Use and Manufacturing

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:314.4
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:314.17427596
Monoisotopic Mass:314.17427596
Topological Polar Surface Area:86.2
Heavy Atom Count:23
Complexity:406
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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