Gardiquimod

Gardiquimod
Identifiers

IUPAC name 1-(4-Amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
CAS Number	1020412-43-4
PubChem (CID)	44592366
ChemSpider	24665048
ChEMBL	CHEMBL1085742
ECHA InfoCard	100.233.311
Chemical and physical data
Formula	C₁₇H₂₃N₅O
Molar mass	313.40 g·mol⁻¹
3D model (Jmol)	Interactive image
SMILES CCNCc1nc2c(n1CC(C)(C)O)c3ccccc3nc2N
InChI InChI=1S/C17H23N5O/c1-4-19-9-13-21-14-15(22(13)10-17(2,3)23)11-7-5-6-8-12(11)20-16(14)18/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20) Key:FHJATBIERQTCTN-UHFFFAOYSA-N
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Gardiquimod is a selective compound for mouse or human toll-like receptor 7 (TLR7) and acts as an immune response modifier.^[1]^[2]^[3] The core structure is 1H-imidazo[4,5-c]quinoline like in both imiquimod and resiquimod. It is structurally extremely similar to resiquimod differing only by an oxygen for nitrogen switch.

References

↑ NCBI: “The TLR7 agonists imiquimod and gardiquimod improve DC-based immunotherapy for melanoma in mice”
↑ NCBI: Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells
↑ Nature.com: “Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells”

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