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 ; trifluoroacetate: 1159840-61-5 ;
PubChem CID	44592366;
ChemSpider	24665048;
UNII	Y3W4QVW5BY; trifluoroacetate: 4Y6M4HJ0WU ;
ChEMBL	ChEMBL1085742;
ECHA InfoCard	100.233.311
Chemical and physical data
Formula	C17H23N5O
Molar mass	313.405 g·mol−1
3D model (JSmol)	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 an experimental drug which acts selectively at both mouse and human forms of toll-like receptor 7 (TLR7). It functions as an immune response modifier.[1][2] The core structure is 1H-imidazo[4,5-c]quinoline, as found in related drugs such as imiquimod and resiquimod. It is structurally very similar to resiquimod differing only by an oxygen for nitrogen switch.

References

Ma F, Zhang J, Zhang J, Zhang C (September 2010). "The TLR7 agonists imiquimod and gardiquimod improve DC-based immunotherapy for melanoma in mice". Cellular & Molecular Immunology. 7 (5): 381–8. doi:10.1038/cmi.2010.30. PMC 4002679. PMID 20543857.
Buitendijk M, Eszterhas SK, Howell AL (June 2013). "Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells". AIDS Research and Human Retroviruses. 29 (6): 907–18. doi:10.1089/aid.2012.0313. PMC 3653394. PMID 23316755.

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[1] Ma F, Zhang J, Zhang J, Zhang C (September 2010). "The TLR7 agonists imiquimod and gardiquimod improve DC-based immunotherapy for melanoma in mice". Cellular & Molecular Immunology. 7 (5): 381–8. doi:10.1038/cmi.2010.30. PMC 4002679. PMID 20543857.

[2] Buitendijk M, Eszterhas SK, Howell AL (June 2013). "Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells". AIDS Research and Human Retroviruses. 29 (6): 907–18. doi:10.1089/aid.2012.0313. PMC 3653394. PMID 23316755.