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;
CompTox Dashboard (EPA)	DTXSID801032731 ;
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.

[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.

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