Resiquimod Sulfate

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H22N4O2.H2O4S
Molecular Weight	412.461
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CCOCC1=NC2=C(N1CC(C)(C)O)C3=C(C=CC=C3)N=C2N

InChI

InChIKey=DGMINEMBFOEPHX-UHFFFAOYSA-N

InChI=1S/C17H22N4O2.H2O4S/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;1-5(2,3)4/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19);(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H22N4O2
Molecular Weight	314.3822
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159603
Curator's Comment: description was created based on several sources, including http://en.pharmacodia.com/web/drug/1_983.html | https://www.ncbi.nlm.nih.gov/pubmed/19841637

Resiquimod is an imidazoquinolinamine and Toll-like receptor (TLR) agonist with potential immune response modifying activity. Resiquimod exerts its effect through the TLR signaling pathway by binding to and activating TLR7 and 8 mainly on dendritic cells, macrophages, and B-lymphocytes. This induces the nuclear translocation of the transcription activator NF-kB as well as activation of other transcription factors. This may lead to an increase in mRNA levels and subsequent production of cytokines, especially interferon-alpha (INF-a) and other cytokines, thereby enhancing T-helper 1 (Th1) immune responses. In addition, topical application of resiquimod appears to activate Langerhans' cells, leading to an enhanced activation of T-lymphocytes. Resiquimod is used as a topical gel[1] in the treatment of skin lesions[2] such as those caused by the herpes simplex virus[3][4] and cutaneous T cell lymphoma. Due to its immunostimulatory activity, this agent may potentially be used as a vaccine adjuvant.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Toll-like receptor 7 13 Target ID: Q9NYK1 Gene ID: 51284.0 Gene Symbol: TLR7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19449004 \| http://pubs.acs.org/doi/abs/10.1021/ml300079e	Agonist 2752		1.4 µM [EC50]
Toll-like receptor 8 4 Target ID: Q9NR97 Gene ID: 51311.0 Gene Symbol: TLR8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19449004 \| http://pubs.acs.org/doi/abs/10.1021/ml300079e	Agonist 2752		6.4 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Cutaneous T-cell lymphoma 10 Sources: https://clinicaltrials.gov/ct2/show/NCT01676831	Primary	Phase II 1147	Unknown Approved Use Unknown
Actinic keratosis 12 Sources: https://clinicaltrials.gov/ct2/show/NCT01583816	Curative	Phase II 1147	Unknown Approved Use Unknown
Warts 10 Sources: https://clinicaltrials.gov/ct2/show/NCT00114920	Curative	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3.82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17532523	0.01 mg/kg single, oral dose: 0.01 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		RESIQUIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.55 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17532523	0.02 mg/kg single, oral dose: 0.02 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		RESIQUIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
45.66 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17532523	0.02 mg/kg single, oral dose: 0.02 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		RESIQUIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.82 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17532523	0.02 mg/kg single, oral dose: 0.02 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		RESIQUIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.02 mg/kg 2 times / week multiple, oral Highest studied dose Dose: 0.02 mg/kg, 2 times / week Route: oral Route: multiple Dose: 0.02 mg/kg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/17532523	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17532523	Disc. AE: Lymphopenia, Lymphopenia... AEs leading to discontinuation/dose reduction: Lymphopenia (grade 3, 9%) Lymphopenia (grade 3, 9%) Flu-like symptoms (grade 3, 9%) Sources: https://pubmed.ncbi.nlm.nih.gov/17532523
0.1 % 3 times / week multiple, topical Studied dose Dose: 0.1 %, 3 times / week Route: topical Route: multiple Dose: 0.1 %, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/18476957	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18476957	Disc. AE: Localized skin reaction... AEs leading to discontinuation/dose reduction: Localized skin reaction Sources: https://pubmed.ncbi.nlm.nih.gov/18476957

AEs

AE	Significance	Dose	Population
Flu-like symptoms	grade 3, 9% Disc. AE	0.02 mg/kg 2 times / week multiple, oral Highest studied dose Dose: 0.02 mg/kg, 2 times / week Route: oral Route: multiple Dose: 0.02 mg/kg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/17532523	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17532523
Lymphopenia	grade 3, 9% Disc. AE	0.02 mg/kg 2 times / week multiple, oral Highest studied dose Dose: 0.02 mg/kg, 2 times / week Route: oral Route: multiple Dose: 0.02 mg/kg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/17532523	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17532523
Lymphopenia	grade 3, 9% Disc. AE	0.02 mg/kg 2 times / week multiple, oral Highest studied dose Dose: 0.02 mg/kg, 2 times / week Route: oral Route: multiple Dose: 0.02 mg/kg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/17532523	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17532523
Localized skin reaction	Disc. AE	0.1 % 3 times / week multiple, topical Studied dose Dose: 0.1 %, 3 times / week Route: topical Route: multiple Dose: 0.1 %, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/18476957	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18476957

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001KQS	https://www.1pchem.com/search?query=1P001KQS
A2B Chem	AA72740	http://a2bchem.com/prod/AA72740
AA Blocks	AA001K7C	http://aablocks.com/goods/Goods/detail?id=AA001K7C
AbovChem LLC	AC051106	http://www.abovchem.com/pc/en/product_list.aspx?wd=AC051106
Achemo Scientific Limited	AC-80519	http://www.achemo.com/search/?Keyword=AC-80519
AK Scientific	Z4166	https://aksci.com/item_detail.php?cat=Z4166
Alfa Chemistry	ACM144875489	http://www.alfa-chemistry.com/search.aspx?q=ACM144875489
Ambeed	A119633	http://www.ambeed.com/search/Search.html?keyword=A119633
Angene	AGN-PC-0PW9KK	http://www.angenechemical.com/productshow/AGN-PC-0PW9KK.html
ApexBio Technology	B1054	https://www.apexbt.com/catalogsearch/result/?q=B1054
Apollo Scientific	BI3860	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BI3860&product_group=%25&search_fieldname=header_search
AstaTech	27389	http://astatechinc.com/CPSResult.php?CRNO=27389
BOC Sciences	144875-48-9	http://www.bocsci.com/description.asp?cas=144875-48-9
Cayman Chemical	14806	http://www.caymanchem.com/app/template/Product.vm/catalog/14806
Chem Scene	CS-1706	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1706
ChemShuttle	152165	https://www.chemshuttle.com/catalogsearch/result/?q=152165
Combi-Blocks	QB-9540	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-9540
eMolecules	31240414	https://orderbb.emolecules.com/search/#?query=31240414
eNovation Chemicals	D583437	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D583437&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A1879	http://www.excenen.com/searchresultlist.php?id=EX-A1879
Fluorochem	223896	http://www.fluorochem.co.uk/Products/Product?code=223896
KeyOrganics	AS-30885	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-30885
Lab Network	LN01307739	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01307739
mcule	MCULE-2339585996	https://mcule.com/MCULE-2339585996/
MedChem Express	HY-13740	https://www.medchemexpress.com/search.html?q=HY-13740&ft=&fa=&fp=
Molnova	M18026	https://www.molnova.com/en/serch-list.html?keywords=M18026
MolPort	MolPort-006-822-593	https://www.molport.com/shop/molecule-link/MolPort-006-822-593
MuseChem	I001738	https://www.musechem.com/product/I001738.html
Selleck Chemicals	S8133	http://www.selleckchem.com/search.html?searchDTO.searchParam=S8133
ShangHai Biochempartner	BCP09103	http://www.biochempartner.com/search_BCP09103
TargetMol	T6964	https://www.targetmol.com/search?keyword=T6964
Tocris	4536	https://www.tocris.com/search.php?Type=QuickSearch&Value=4536
Toronto Research Chemicals	C587535	https://www.trc-canada.com/product-detail/?CatNum=C587535
Toronto Research Chemicals	R150140	https://www.trc-canada.com/product-detail/?CatNum=R150140
Toronto Research Chemicals	R150143	https://www.trc-canada.com/product-detail/?CatNum=R150143
W&J PharmaChem	50C1499059	http://wjpharmachem.com/new/searcht.php?keyword=50C1499059
Wonderchem	WD02PCG	http://www.wonder-chem.com/search.html?text=WD02PCG

PubMed

Title	Date	PubMed
Selective inhibition of the NLRP3 inflammasome by targeting to promyelocytic leukemia protein in mouse and human.	2013-04-18	23430110
A critical role for MAPK signalling pathways in the transcriptional regulation of toll like receptors.	2013	23405061
Tetra-O-methyl nordihydroguaiaretic acid (Terameprocol) inhibits the NF-κB-dependent transcription of TNF-α and MCP-1/CCL2 genes by preventing RelA from binding its cognate sites on DNA.	2010-12-07	21138578
An intranasally delivered Toll-like receptor 7 agonist elicits robust systemic and mucosal responses to Norwalk virus-like particles.	2010-12	20962211
Inhibition of the type I interferon antiviral response during arenavirus infection.	2010-11	21994626
Cellular and molecular mechanisms underlying the strong neonatal IL-12 response of lamb mesenteric lymph node cells to R-848.	2010-10-28	21060840
Protective effects of Sm-p80 in the presence of resiquimod as an adjuvant against challenge infection with Schistosoma mansoni in mice.	2010-09	20630783
TLR8 agonists stimulate newly recruited monocyte-derived cells into potent APCs that enhance HBsAg immunogenicity.	2010-08-31	20637759
Herpes simplex virus and human papillomavirus genital infections: new and investigational therapeutic options.	2010-07	20618491
Dendritic cells in uninfected infants born to hepatitis B virus-positive mothers.	2010-07	20463102
2,3,7,8-tetrachlorodibenzo-p-dioxin-mediated suppression of toll-like receptor stimulated B-lymphocyte activation and initiation of plasmacytic differentiation.	2010-07	20348231
Immune mechanisms of protection: can adjuvants rise to the challenge?	2010-04-12	20385031
Topical resiquimod: a promising adjuvant for vaccine development?	2010-01	20021302
The Toll-like receptor 7/8 agonist resiquimod greatly increases the immunostimulatory capacity of human acute myeloid leukemia cells.	2010-01	19449004
Targeting Toll-like receptors for treatment of SLE.	2010	20886024
Toll-like receptors: role in dermatological disease.	2010	20847936
Molecular modulation of intestinal epithelial barrier: contribution of microbiota.	2010	20150966
Short-term cultured, interleukin-15 differentiated dendritic cells have potent immunostimulatory properties.	2009-12-18	20021667
Pharmacotherapy of actinic keratosis.	2009-12	19925043
Toward the discovery of vaccine adjuvants: coupling in silico screening and in vitro analysis of antagonist binding to human and mouse CCR4 receptors.	2009-11-30	20011659
Growth inhibition of thyroid follicular cell-derived cancers by the opioid growth factor (OGF) - opioid growth factor receptor (OGFr) axis.	2009-10-18	19835629
Nanoparticle-delivered multimeric soluble CD40L DNA combined with Toll-Like Receptor agonists as a treatment for melanoma.	2009-10-08	19812695
Topical resiquimod promotes priming of CTL to parenteral antigens.	2009-09-25	19660592
Modulation of the allergic asthma transcriptome following resiquimod treatment.	2009-08-07	19491150
Sequence determinants of innate immune activation by short interfering RNAs.	2009-07-24	19630977
Oxidative stress augments toll-like receptor 8 mediated neutrophilic responses in healthy subjects.	2009-06-15	19527497
Do postsurgical interventions optimize ultimate scar cosmesis.	2009-06	19528906
Rectal and vaginal immunization of mice with human papillomavirus L1 virus-like particles.	2009-04-14	19428847
Reversal of human papillomavirus-specific T cell immune suppression through TLR agonist treatment of Langerhans cells exposed to human papillomavirus type 16.	2009-03-01	19234187
Expression and activity of Toll-like receptors 1-9 in the human term placenta and changes associated with labor at term.	2009-02	18815357
Toll-like receptor 7-induced naive human B-cell differentiation and immunoglobulin production.	2009-01	18995892
TLR7 and TLR8 ligands and antiphospholipid antibodies show synergistic effects on the induction of IL-1beta and caspase-1 in monocytes and dendritic cells.	2009	19249118
Hepatitis C virus is a weak inducer of interferon alpha in plasmacytoid dendritic cells in comparison with influenza and human herpesvirus type-1.	2009	19183807
Imiquimod upregulates the opioid growth factor receptor to inhibit cell proliferation independent of immune function.	2008-08	18480416
Comparison of human B cell activation by TLR7 and TLR9 agonists.	2008-07-24	18652679
A phase II dose-ranging study of topical resiquimod to treat actinic keratosis.	2008-07	18476957
Differential regulation of interleukin 12 and interleukin 23 production in human dendritic cells.	2008-06-09	18490488
Intra-colonic administration of the TLR7 agonist R-848 induces an acute local and systemic inflammation in mice.	2008-03-07	18083110
TLR7 and TLR8 as targets in cancer therapy.	2008-01-07	18176600
Toll-like receptors and viruses: induction of innate antiviral immune responses.	2008	19088911
Primary prevention of allergic diseases: current concepts and mechanisms.	2007-12-15	20525115
HIV-1/HSV-2 co-infected adults in early HIV-1 infection have elevated CD4+ T cell counts.	2007-10-24	17957262
Transcriptional networks in plasmacytoid dendritic cells stimulated with synthetic TLR 7 agonists.	2007-10-12	17935622
Resiquimod and other immune response modifiers as vaccine adjuvants.	2007-10	17931162
TLR agonists induce the differentiation of human bone marrow CD34+ progenitors into CD11c+ CD80/86+ DC capable of inducing a Th1-type response.	2007-10	17853407
Impaired CCR7 expression on plasmacytoid dendritic cells of HIV-infected children and adolescents with immunologic and virologic failure.	2007-08-15	17468665
Oral resiquimod in chronic HCV infection: safety and efficacy in 2 placebo-controlled, double-blind phase IIa studies.	2007-08	17532523
Topical resiquimod 0.01% gel decreases herpes simplex virus type 2 genital shedding: a randomized, controlled trial.	2007-05-01	17397003
Generation of clinical grade dendritic cells with capacity to produce biologically active IL-12p70.	2007-04-12	17430585
Natural and synthetic TLR7 ligands inhibit CpG-A- and CpG-C-oligodeoxynucleotide-induced IFN-alpha production.	2007-04-01	17371961

Patents

Sample Use Guides

In Vivo Use Guide

Topical -- up to 500 mg of resiquimod as a gel (0.06% and 0.03%) covering a surface area of up to 100 cm^2. Oral -- 0.01 mg/kg dose of resiquimod twice weekly for 4 weeks.

Route of Administration: Other

In Vitro Use Guide

THP-1 cells were exposed for 2, 4, 8 and 16 h with 0.1 mg/ml of resiquimod. Resiquimod induce decrease in hypoxia-inducible factor-1a (HIF-1a) prolyl hydroxylase (PHD) activity

Substance Class	Chemical Created by `admin` on `Tue Apr 01 20:55:07 GMT 2025` Edited by `admin` on `Tue Apr 01 20:55:07 GMT 2025`
Record UNII	C8FKIS4P1N
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Resiquimod Sulfate

Official Name

English

BDB-001

Preferred Name

English

C151008135D

Code

English

C151008135-D

Code

English

RESIQUIMOD SULFATE [USAN]

Common Name

English

EIK-1001 sulfate

Code

English

1H-Imidazo[4,5-c]quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-?,?-dimethyl-, sulfate (1:1)

Systematic Name

English

EIK1001 sulfate

Code

English

BDB 001 [WHO-DD]

Common Name

English

4-Amino-2-(ethoxymethyl)-1-(2-hydroxisobutyl) imidazo[4,5-c]quinoline, sulfate (1:1)

Systematic Name

English

BDB001

Code

English

Code System Code Type Description

CAS

2762439-40-5