852A   Click here for help

GtoPdb Ligand ID: 9025

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 852A is a soluble agonist of Toll-like receptor 7 (TLR7) [5]. It has been clinically investigated for potential anti-cancer activity [1-4,6].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 111.28
Molecular weight 361.16
XLogP 2.05
No. Lipinski's rules broken 0
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Canonical SMILES CCc1nc2c(n1CCCCNS(=O)(=O)C)c1ccccc1nc2N
Isomeric SMILES CCc1nc2c(n1CCCCNS(=O)(=O)C)c1ccccc1nc2N
InChI InChI=1S/C17H23N5O2S/c1-3-14-21-15-16(12-8-4-5-9-13(12)20-17(15)18)22(14)11-7-6-10-19-25(2,23)24/h4-5,8-9,19H,3,6-7,10-11H2,1-2H3,(H2,18,20)
1. Chi H, Li C, Zhao FS, Zhang L, Ng TB, Jin G, Sha O. (2017)
Anti-tumor Activity of Toll-Like Receptor 7 Agonists.
Front Pharmacol, 8: 304. [PMID:28620298]
2. Dudek AZ, Yunis C, Harrison LI, Kumar S, Hawkinson R, Cooley S, Vasilakos JP, Gorski KS, Miller JS. (2007)
First in human phase I trial of 852A, a novel systemic toll-like receptor 7 agonist, to activate innate immune responses in patients with advanced cancer.
Clin Cancer Res, 13 (23): 7119-25. [PMID:18056192]
3. Dummer R, Hauschild A, Becker JC, Grob JJ, Schadendorf D, Tebbs V, Skalsky J, Kaehler KC, Moosbauer S, Clark R et al.. (2008)
An exploratory study of systemic administration of the toll-like receptor-7 agonist 852A in patients with refractory metastatic melanoma.
Clin Cancer Res, 14 (3): 856-64. [PMID:18245549]
4. Geller MA, Cooley S, Argenta PA, Downs LS, Carson LF, Judson PL, Ghebre R, Weigel B, Panoskaltsis-Mortari A, Curtsinger J et al.. (2010)
Toll-like receptor-7 agonist administered subcutaneously in a prolonged dosing schedule in heavily pretreated recurrent breast, ovarian, and cervix cancers.
Cancer Immunol Immunother, 59 (12): 1877-84. [PMID:20820775]
5. Nakamura T, Wada H, Kurebayashi H, McInally T, Bonnert R, Isobe Y. (2013)
Synthesis and evaluation of 8-oxoadenine derivatives as potent Toll-like receptor 7 agonists with high water solubility.
Bioorg Med Chem Lett, 23 (3): 669-72. [PMID:23265901]
6. Weigel BJ, Cooley S, DeFor T, Weisdorf DJ, Panoskaltsis-Mortari A, Chen W, Blazar BR, Miller JS. (2012)
Prolonged subcutaneous administration of 852A, a novel systemic toll-like receptor 7 agonist, to activate innate immune responses in patients with advanced hematologic malignancies.
Am J Hematol, 87 (10): 953-6. [PMID:22718533]