Resiquimod
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Resiquimod
- DrugBank Accession Number
- DB06530
- Background
A substance being studied in the treatment of some types of skin cancer. When put on the skin, resiquimod causes some immune cells to make certain chemicals that may help them kill tumor cells. It is also being studied to find out if adding it to a tumor vaccine improves the antitumor immune response. It is a type of imidazoquinoline and a type of immunomodulator.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Resiquimod (DB06530)
- Weight
- Average: 314.3822
Monoisotopic: 314.174275968 - Chemical Formula
- C17H22N4O2
- Synonyms
- Resiquimod
- External IDs
- R 848
- R-848
- R848
Pharmacology
- Indication
Investigated for use/treatment in genital herpes.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Resiquimod is a Toll-like receptor 7 (TLR7) and TLR8 agonist that is a potent inducer of alpha interferon (IFN-alpha) and other cytokines.
Target Actions Organism UToll-like receptor 7 Not Available Humans UToll-like receptor 8 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Imidazoquinolines
- Direct Parent
- Imidazoquinolines
- Alternative Parents
- Aminoquinolines and derivatives / Imidazo-[4,5-c]pyridines / Aminopyridines and derivatives / N-substituted imidazoles / Imidolactams / Benzenoids / Tertiary alcohols / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds show 3 more
- Substituents
- Alcohol / Amine / Aminopyridine / Aminoquinoline / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Dialkyl ether / Ether show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- imidazoquinoline (CHEBI:36706)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- V3DMU7PVXF
- CAS number
- 144875-48-9
- InChI Key
- BXNMTOQRYBFHNZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)
- IUPAC Name
- 1-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
- SMILES
- CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)O
References
- General References
- Sauder DN, Smith MH, Senta-McMillian T, Soria I, Meng TC: Randomized, single-blind, placebo-controlled study of topical application of the immune response modulator resiquimod in healthy adults. Antimicrob Agents Chemother. 2003 Dec;47(12):3846-52. [Article]
- External Links
- ChemSpider
- 140330
- BindingDB
- 50241029
- ChEBI
- 36706
- ChEMBL
- CHEMBL383322
- ZINC
- ZINC000028572103
- PDBe Ligand
- RX8
- Wikipedia
- Resiquimod
- PDB Entries
- 3w3l / 3w3m / 3w3n / 5ans / 5gmh
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Active Not Recruiting Treatment Anaplastic Astro-oligodendroglioma / Anaplastic Astrocytoma (AA) / Glioblastoma Multiforme (GBM) / Gliomas 1 2 Completed Treatment Actinic Keratosis (AK) 1 2 Completed Treatment Malignant Melanoma of Skin 1 2 Completed Treatment Verruca (Warts) 6 1 Completed Treatment Influenza Vaccination in Seniors 1 1 Completed Treatment Tumors 1 1, 2 Completed Prevention Viral Hepatitis B 1 1, 2 Completed Treatment Advanced Malignancies 1 1, 2 Completed Treatment Cutaneous T Cell Lymphomas (CTCL) 1 1, 2 Terminated Basic Science Nodular Basal Cell Carcinoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.241 mg/mL ALOGPS logP 2.24 ALOGPS logP 1.72 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 14.91 ChemAxon pKa (Strongest Basic) 4.83 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 86.19 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 89.79 m3·mol-1 ChemAxon Polarizability 35.01 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR7 i...
- Gene Name
- TLR7
- Uniprot ID
- Q9NYK1
- Uniprot Name
- Toll-like receptor 7
- Molecular Weight
- 120920.8 Da
References
- Weeratna RD, Makinen SR, McCluskie MJ, Davis HL: TLR agonists as vaccine adjuvants: comparison of CpG ODN and Resiquimod (R-848). Vaccine. 2005 Nov 1;23(45):5263-70. Epub 2005 Jul 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Single-stranded rna binding
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. Acts v...
- Gene Name
- TLR8
- Uniprot ID
- Q9NR97
- Uniprot Name
- Toll-like receptor 8
- Molecular Weight
- 119826.82 Da
References
- Weeratna RD, Makinen SR, McCluskie MJ, Davis HL: TLR agonists as vaccine adjuvants: comparison of CpG ODN and Resiquimod (R-848). Vaccine. 2005 Nov 1;23(45):5263-70. Epub 2005 Jul 18. [Article]
Drug created on March 19, 2008 16:36 / Updated on February 21, 2021 18:52