imiquimod   

GtoPdb Ligand ID: 5003

Synonyms: Aldara® | R837 | S-26308 | Zyclara®
imiquimod is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: Imiquimod is a TLR7 agonist acting as an immunomodulator.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 56.73
Molecular weight 240.14
XLogP 2.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(Cn1cnc2c1c1ccccc1nc2N)C
Isomeric SMILES CC(Cn1cnc2c1c1ccccc1nc2N)C
InChI InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
InChI Key DOUYETYNHWVLEO-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Used in the topical treatment of warts on the skin of the genital and anal areas, as well as treatment of actinic keratosis and superficial basal cell carcinoma.
Mechanism Of Action and Pharmacodynamic Effects
Imiquimod is a Toll-like receptor 7 (TLR7) agonist. Imiquimod stimulates the innate and acquired immune responses (by inducing cytokine production and release) and increases inflammatory cell recruitment at the site of drug application. This leads to apoptosis of diseased tissue.
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