resiquimod   Click here for help

GtoPdb Ligand ID: 5051

Synonyms: R-848 | R848
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Resiquimod (R-848) is a more potent derivative of the imidazoquinoline compound imiquimod [1]. It acts as a TLR7 agonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 86.19
Molecular weight 314.17
XLogP 1.94
No. Lipinski's rules broken 0
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Canonical SMILES CCOCc1nc2c(n1CC(O)(C)C)c1ccccc1nc2N
Isomeric SMILES CCOCc1nc2c(n1CC(O)(C)C)c1ccccc1nc2N
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)
1. Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S. (2002)
Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway.
Nat Immunol, 3 (2): 196-200. [PMID:11812998]
2. Jurk M, Heil F, Vollmer J, Schetter C, Krieg AM, Wagner H, Lipford G, Bauer S. (2002)
Human TLR7 or TLR8 independently confer responsiveness to the antiviral compound R-848.
Nat Immunol, 3 (6): 499. [PMID:12032557]
3. Larson P, Kucaba TA, Xiong Z, Olin M, Griffith TS, Ferguson DM. (2017)
Design and Synthesis of N1-Modified Imidazoquinoline Agonists for Selective Activation of Toll-like Receptors 7 and 8.
ACS Med Chem Lett, 8 (11): 1148-1152. [PMID:29152046]
4. Stockfleth E, Hofbauer GFL, Reinhold U, Popp G, Hengge UR, Szeimies RM, Brüning H, Anliker M, Hunger T, Dummer R et al.. (2019)
Topical resiquimod dosing regimens in patients with multiple actinic keratoses: a multicentre, partly placebo-controlled, double-blind clinical trial.
Br J Dermatol, 180 (2): 297-305. [PMID:30171698]