MedKoo Cat#: 565133 | Name: Gardiquimod HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Gardiquimod HCl
Gardiquimod HCl
CAS#2956183-81-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 565133

Name: Gardiquimod HCl

CAS#: 2956183-81-4 (HCl)

Chemical Formula: C17H24ClN5O

Exact Mass: 0.0000

Molecular Weight: 349.86

Elemental Analysis: C, 58.36; H, 6.91; Cl, 10.13; N, 20.02; O, 4.57

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Gardiquimod hydrochloride; Gardiquimod HCl
IUPAC/Chemical Name
1-[4-Amino-2-(ethylaminomethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol hydrochloride
InChi Key
YHVYOGAFUOQBOL-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H23N5O.ClH/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);1H
SMILES Code
CC(O)(C)CN1C(CNCC)=NC2=C1C3=CC=CC=C3N=C2N.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 349.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.