Details of the Drug

General Information of Drug (ID: DML6XSP)

Drug Name
Resiquimod
Synonyms
Resiquimod [INN]; R 848; S 28463; R-848; S-28463; VML-600; 1-(4-Amino-2-ethoxymethyl-imidazo[4,5-c]quinolin-1-yl)-2-methyl-propan-2-ol; 1-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol; 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol; 4-amino-2-(ethoxymethyl)-a,a-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol; 4-amino-2-ethoxymethyl-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol
Indication
Disease Entry ICD 11 Status REF
Actinic keratosis EK90.0 Phase 2 [1]
Cutaneous T-cell lymphoma 2B01 Phase 2 [2]
Herpes simplex virus infection 1F00 Phase 1/2 [3], [4]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 314.4
Topological Polar Surface Area (xlogp) 1.3
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C17H22N4O2
IUPAC Name
1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
Canonical SMILES
CCOCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N
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)
InChIKey
BXNMTOQRYBFHNZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
159603
ChEBI ID
CHEBI:36706
CAS Number
144875-48-9
DrugBank ID
DB06530
TTD ID
D0C8KF

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Toll-like receptor 7 (TLR7) TTRJ1K4 TLR7_HUMAN Modulator [5]
Toll-like receptor 8 (TLR8) TT8CWFK TLR8_HUMAN Modulator [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Actinic keratosis
ICD Disease Classification EK90.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Toll-like receptor 7 (TLR7) DTT TLR7 3.32E-25 0.44 0.88
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT01583816) Dose-finding, Safety, Efficacy Trial of Topical Resiquimod in Patients With Multiple Actinic Keratosis Lesions. U.S. National Institutes of Health.
2 ClinicalTrials.gov (NCT03292406) A Safety, Efficacy and Pharmacokinetics Study of CD11301 for the Treatment of Cutaneous T-Cell Lymphoma (CTCL) (CTCL). U.S. National Institutes of Health.
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5051).
4 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800010858)
5 TLR agonists as vaccine adjuvants: comparison of CpG ODN and Resiquimod (R-848).Vaccine.2005 Nov 1;23(45):5263-70.
6 Imiquimod enhances IFN-gamma production and effector function of T cells infiltrating human squamous cell carcinomas of the skin. J Invest Dermatol. 2009 Nov;129(11):2676-85.
7 TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35.
8 Clinical pipeline report, company report or official report of Anadys Pharmaceuticals (2011).
9 Pharmacokinetic and pharmacodynamic properties of GS-9620, a novel Toll-like receptor 7 agonist, demonstrate interferon-stimulated gene induction without detectable serum interferon at low oral doses. J Pharmacol Exp Ther. 2014 Jan;348(1):96-105.
10 Company report (Iderapharma)
11 The Toll-like receptor 7 (TLR7)-specific stimulus loxoribine uncovers a strong relationship within the TLR7, 8 and 9 subfamily. Eur J Immunol. 2003 Nov;33(11):2987-97.
12 Early clinical evaluation of the intranasal TLR7 agonist GSK2245035: Use of translational biomarkers to guide dosing and confirm target engagement. Clin Pharmacol Ther. 2015 Oct;98(4):369-80.
13 Repeated intranasal TLR7 stimulation reduces allergen responsiveness in allergic rhinitis. Respir Res. 2012 Jun 22;13:53.
14 Discovery of ANA975: an oral prodrug of the TLR-7 agonist isatoribine. Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):635-40.
15 The innate immune response, clinical outcomes, and ex vivo HCV antiviral efficacy of a TLR7 agonist (PF-4878691). Clin Pharmacol Ther. 2011 Jun;89(6):821-9.
16 Discovery of GS-9688 (Selgantolimod) as a Potent and Selective Oral Toll-Like Receptor 8 Agonist for the Treatment of Chronic Hepatitis B. J Med Chem. 2020 Sep 24;63(18):10188-10203.
17 Clinical pipeline report, company report or official report of Nektar Therapeutics.
18 Coley Pharmaceutical Group Diversifies Pipeline with First-in-Class TLR Antagonist for the Treatment of Systemic Lupus Erythematosus. Lupus Foundation of America, Inc. 2007.
19 Clinical pipeline report, company report or official report of CureVac.
20 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
21 Clinical pipeline report, company report or official report of Silverback Therapeutics.
22 VTX-1463, a novel TLR8 agonist for the treatment of allergic rhinitis. Expert Opin Investig Drugs. 2011 Jul;20(7):981-6.
23 Clinical pipeline report, company report or official report of Shanghai De Novo Pharmatech.
24 Clinical pipeline report, company report or official report of Array BioPharma (Drug: Motolimod / VTX2337).
25 Clinical pipeline report, company report or official report of Idera Pharmaceuticals.