Resiquimod

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Resiquimod
Accession Number
DB06530
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
R-848 / R848
Categories
Not Available
UNII
V3DMU7PVXF
CAS number
144875-48-9
Weight
Average: 314.3822
Monoisotopic: 314.174275968
Chemical Formula
C17H22N4O2
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-[2-(ethoxymethyl)-4-imino-1H,4H,5H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
SMILES
CCOCC1=NC2=C(N1CC(C)(C)O)C1=CC=CC=C1NC2=N

Pharmacology

Indication

Investigated for use/treatment in genital herpes.

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
UToll-like receptor 7Not AvailableHumans
UToll-like receptor 8Not AvailableHumans
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:14638493]
External Links
ChemSpider
140330
BindingDB
50241029
ChEBI
36706
ChEMBL
CHEMBL383322
HET
RX8
Wikipedia
Resiquimod
PDB Entries
3w3l / 3w3m / 3w3n / 5ans / 5gmh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentMelanoma (Skin)1
0CompletedTreatmentRecurrent Melanoma / Stage IIA Melanoma / Stage IIB Melanoma / Stage IIC Melanoma / Stage IIIA Melanoma / Stage IIIB Melanoma / Stage IIIc Melanoma / Stage IV Melanoma1
1CompletedTreatmentInfluenza Vaccination in Seniors1
1, 2CompletedPreventionViral Hepatitis B1
1, 2CompletedTreatmentAdvanced Malignancies1
1, 2CompletedTreatmentCutaneous T Cell Lymphomas (CTCL)1
2Active Not RecruitingTreatmentMelanoma1
2CompletedTreatmentActinic Keratosis (AK)1
2CompletedTreatmentWarts6

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 Solubility0.312 mg/mLALOGPS
logP1.55ALOGPS
logP1.48ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)14.93ChemAxon
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.16 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.49 m3·mol-1ChemAxon
Polarizability34.95 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Imidazoquinoline / Aminoquinoline / Imidazopyridine / Imidazo-[4,5-c]pyridine / Aminopyridine / Imidolactam / Benzenoid / Pyridine / N-substituted imidazole / Azole
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
imidazoquinoline (CHEBI:36706)

Targets

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
  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. [PubMed:16081189]
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
  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. [PubMed:16081189]

Drug created on March 19, 2008 10:36 / Updated on August 02, 2019 07:52