Gardiquimod - ≥97% , CAS No.1020412-43-4

CAS: 1020412-43-4 Cat. No.: G274801 Molecular Weight: 313.4 EC Number: 806-274-5

GRADE & PURITY ≥97%

Synonyms

1-[4-amino-2-(ethylaminomethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol | 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol | 1-(4-amino-2-ethylaminomethylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Biochem/physiol Actions

Gardiquimod is a potent and specific agonist for human or mouse Toll-like receptor 7 (TLR7). Also, at high concentration gardiquimod activates TLR8. Similarly to imiquimod, gardiquimod could mimic the effects of viral nucleic acids on the immune system.

Gardiquimod is developed as a new imidazoquinoline compound. It stimulates NF-κB (nuclear factor-κB) activation in cells expressing human or murine toll like receptor 7 (TLR7). Gardiquimod is found to be ten times more efficient than imiquimod. It induces splenocyte activation and prevents murine B16 melanoma growth and metastasis. Gardiquimod might serve as a therapeutic agent to prevent HIV-1 (human immunodeficiency virus - 1) transmission. It hinders the life cycle of HIV-1, by blocking the action of HIV-1 reverse transcriptase.

Specifications

Synonyms

1-[4-amino-2-(ethylaminomethyl)imidazo[4, 5-c]quinolin-1-yl]-2-methylpropan-2-ol | 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4, 5-c]quinolin-1-yl)-2-methylpropan-2-ol | 1-(4-amino-2-ethylaminomethylimidazo[4, 5-c]quinolin-1-yl)-2-methylpropan-2-ol

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

Selective TLR7 agonist. Inhibits HIV-1 reverse transcriptase. Induces pro-inflammatory cytokine production in thymocytes. Antiproliferative effects. Shows immunomodulatory effects in vivo. More active than Imiquimod.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥97%

Names and Identifiers

• Canonical Smiles: CCNCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N
• IUPAC Name: 1-[4-amino-2-(ethylaminomethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
• InChIKey: FHJATBIERQTCTN-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: CCNCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N
• Molecular Weight: 313.4
• Reaxy-Rn: 19659786
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=19659786&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Imidazoquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Imidazoquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Imidazoquinolines
• Alternative Parents: Aminoquinolines and derivatives Imidazo-[4,5-c]pyridines Aralkylamines Aminopyridines and derivatives N-substituted imidazoles Imidolactams Benzenoids Tertiary alcohols Heteroaromatic compounds Dialkylamines Azacyclic compounds Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Imidazoquinoline - Aminoquinoline - Imidazopyridine - Imidazo-[4,5-c]pyridine - Aminopyridine - Aralkylamine - N-substituted imidazole - Pyridine - Benzenoid - Imidolactam - Tertiary alcohol - Imidazole - Azole - Heteroaromatic compound - Secondary amine - Secondary aliphatic amine - Azacycle - Amine - Primary amine - Organooxygen compound - Organonitrogen compound - Alcohol - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as imidazoquinolines. These are aromatic heterocyclic compounds containing an imidazole ring fused to a quinoline ring system. In some configurations, the imidazole ring shares a nitrogen atom with the quinoline moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TLR8 Tchem Toll-like receptor 8 (1853 Activities)

Discover Target: TLR8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Tlr7 Toll-like receptor 7 (174 Activities)

Discover Target: Tlr7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 100 mM
• Molecular Weight: 313.400 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 313.19 Da
• Monoisotopic Mass: 313.19 Da
• Topological Polar Surface Area: 89.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 404.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xiaolong Li, Lanlan Ma, Jueshuo Guo, Yaya Wei, Shijie Ma, Yaping Mai, Guojing Gou, Wenbao Zuo, Jianhong Yang.  (2025)  Synergistic anti-tumor effects of mRNA vaccine and PERK inhibitor combination in melanoma treatment.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:40383023] [10.1016/j.colsurfb.2025.114808]