WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 330135
CAS#: 1159840-61-5 (TFA)
Description: Gardiquimod is a chemical compound which acts selectively at both mouse and human forms of toll-like receptor 7 (TLR7). It functions as an immune response modifier. 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.
MedKoo Cat#: 330135
Name: Gardiquimod TFA
CAS#: 1159840-61-5 (TFA)
Chemical Formula: C19H24F3N5O3
Exact Mass:
Molecular Weight: 427.43
Elemental Analysis: C, 53.39; H, 5.66; F, 13.33; N, 16.39; O, 11.23
Related CAS #: 1159840-61-5 (TFA) 1020412-43-4 (free base)
Synonym: Gardiquimod TFA salt; Gardiquimod;
IUPAC/Chemical Name: 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol 2,2,2-trifluoroacetate
InChi Key: POTWNBLXWPBSSG-UHFFFAOYSA-N
InChi Code: InChI=1S/C17H23N5O.C2HF3O2/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;3-2(4,5)1(6)7/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20);(H,6,7)
SMILES Code: CC(O)(C)CN1C(CNCC)=NC2=C1C3=CC=CC=C3N=C2N.O=C(O)C(F)(F)F
1: Guo S, Zhang Y, Wang Z, Yu Y, Wang G. Intraperitoneal gardiquimod protects
against hepatotoxicity through inhibition of oxidative stress and inflammation in
mice with sepsis. J Biochem Mol Toxicol. 2017 Aug;31(8). doi: 10.1002/jbt.21923.
Epub 2017 Apr 19. PubMed PMID: 28422377.
2: Jia B, Luo X, Cheng FW, Li L, Hu DJ, Wang F, Zhang SQ. Gardiquimod inhibits
the expression of calcium-induced differentiation markers in HaCaT cells. Mol
Biol Rep. 2013 Nov;40(11):6363-9. doi: 10.1007/s11033-013-2750-9. Epub 2013 Sep
22. PubMed PMID: 24057248.
3: Buitendijk M, Eszterhas SK, Howell AL. Gardiquimod: a Toll-like receptor-7
agonist that inhibits HIV type 1 infection of human macrophages and activated T
cells. AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. doi:
10.1089/AID.2012.0313. Epub 2013 Feb 5. PubMed PMID: 23316755; PubMed Central
PMCID: PMC3653394.
4: Ma F, Zhang J, Zhang J, Zhang C. The TLR7 agonists imiquimod and gardiquimod
improve DC-based immunotherapy for melanoma in mice. Cell Mol Immunol. 2010
Sep;7(5):381-8. doi: 10.1038/cmi.2010.30. Epub 2010 Jun 14. PubMed PMID:
20543857; PubMed Central PMCID: PMC4002679.