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Resiquimod

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Data Packages
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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
3D
Similar Structures
Weight
Average: 314.3822
Monoisotopic: 314.174275968
Chemical Formula
C17H22N4O2
Synonyms
  • Resiquimod
External IDs
  • R 848
  • R-848
  • R848
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Pharmacology

Indication

Investigated for use/treatment in genital herpes.

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AToll-like receptor 7
modulator
Humans
AToll-like receptor 8
modulator
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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
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
  1. 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]
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
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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Not AvailableRecruitingBasic ScienceAsthma / Coronavirus Disease 2019 (COVID‑19) / Innate Immunity / Mucosal Immunity / Viral Infections1somestatusstop reasonjust information to hide
Not AvailableRecruitingBasic ScienceAsthma / Coronavirus Disease 2019 (COVID‑19) / Innate Inflammatory Response / Nasal Allergies1somestatusstop reasonjust information to hide
2CompletedTreatmentActinic Keratosis (AK)1somestatusstop reasonjust information to hide
2CompletedTreatmentAnaplastic Astro-oligodendroglioma / Anaplastic Astrocytoma (AA) / Glioma / High Grade Glioma: Glioblastoma (GBM)1somestatusstop reasonjust information to hide
2CompletedTreatmentMelanoma1somestatusstop reasonjust information to hide

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
PropertyValueSource
Water Solubility0.241 mg/mLALOGPS
logP2.24ALOGPS
logP1.72Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.91Chemaxon
pKa (Strongest Basic)4.83Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area86.19 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity89.79 m3·mol-1Chemaxon
Polarizability35.01 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-7190000000-59824670b0b9164d06fd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0049000000-ed68db50ac14d0c8b240
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0095000000-cf864ad23ccdf13b0548
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w29-0094000000-92fc1f370ff00faf7d52
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fs-0092000000-f2640e57099a00acdde1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p2-0590000000-67777101a9d64c384531
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0560-2390000000-9fca5a05aaa0bc9f798c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.2572767
predicted
DarkChem Lite v0.1.0
[M-H]-173.21176
predicted
DeepCCS 1.0 (2019)
[M+H]+184.2324767
predicted
DarkChem Lite v0.1.0
[M+H]+175.56978
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.9511
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Toll-like receptor 7
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Endosomal receptor that plays a key role in innate and adaptive immunity (PubMed:14976261, PubMed:32433612). Controls host immune response against pathogens through recognition of uridine-containing single strand RNAs (ssRNAs) of viral origin or guanosine analogs (PubMed:12738885, PubMed:27742543, PubMed:31608988, PubMed:32706371, PubMed:35477763). Upon binding to agonists, undergoes dimerization that brings TIR domains from the two molecules into direct contact, leading to the recruitment of TIR-containing downstream adapter MYD88 through homotypic interaction (PubMed:27742543). In turn, the Myddosome signaling complex is formed involving IRAK4, IRAK1, TRAF6, TRAF3 leading to activation of downstream transcription factors NF-kappa-B and IRF7 to induce pro-inflammatory cytokines and interferons, respectively (PubMed:27742543, PubMed:32706371)
Specific Function
double-stranded RNA binding
Gene Name
TLR7
Uniprot ID
Q9NYK1
Uniprot Name
Toll-like receptor 7
Molecular Weight
120920.8 Da
References
  1. 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]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details2. Toll-like receptor 8
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Endosomal receptor that plays a key role in innate and adaptive immunity (PubMed:25297876, PubMed:32433612). Controls host immune response against pathogens through recognition of RNA degradation products specific to microorganisms that are initially processed by RNASET2 (PubMed:31778653). Recognizes GU-rich single-stranded RNA (GU-rich RNA) derived from SARS-CoV-2, SARS-CoV-1 and HIV-1 viruses (PubMed:33718825). Upon binding to agonists, undergoes dimerization that brings TIR domains from the two molecules into direct contact, leading to the recruitment of TIR-containing downstream adapter MYD88 through homotypic interaction (PubMed:23520111, PubMed:25599397, PubMed:26929371, PubMed:33718825). In turn, the Myddosome signaling complex is formed involving IRAK4, IRAK1, TRAF6, TRAF3 leading to activation of downstream transcription factors NF-kappa-B and IRF7 to induce pro-inflammatory cytokines and interferons, respectively (PubMed:16737960, PubMed:17932028, PubMed:29155428)
Specific Function
DNA binding
Gene Name
TLR8
Uniprot ID
Q9NR97
Uniprot Name
Toll-like receptor 8
Molecular Weight
119826.82 Da
References
  1. 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]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at March 19, 2008 16:36 / Updated at August 26, 2024 19:23