Resiquimod
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 205867

CAS#: 144875-48-9

Description: Resiquimod, also known as R-848; S-28463; VML-600, is a n imidazoquinolinamine Toll-like receptor (TLR) agonist with potential immunostimulatory activity. Resiquimod binds to and activates TLRs 7 and 8, mainly on dendritic cells (DCs), macrophages, and B-lymphocytes, which results in the activation of the TLR signaling pathway and nuclear translocation of the transcription activator NF-kB another transcription factors; subsequently, the production of cytokines, especially interferon-alpha (INF-a), increases, enhancing T-helper 1 (Th1) immune responses. In addition, topical application of resiquimod appears to activate Langerhans cells, which may result in enhanced activation of T-lymphocytes.


Chemical Structure

img
Resiquimod
CAS# 144875-48-9

Theoretical Analysis

MedKoo Cat#: 205867
Name: Resiquimod
CAS#: 144875-48-9
Chemical Formula: C17H22N4O2
Exact Mass: 314.17428
Molecular Weight: 314.38218
Elemental Analysis: C, 64.95; H, 7.05; N, 17.82; O, 10.18

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Same day
200.0mg USD 250.0 Same day
500.0mg USD 450.0 Same day
1.0g USD 750.0 Same day
2.0g USD 1250.0 Same day
5.0g USD 2750.0 2 weeks
10.0g USD 4950.0 2 weeks
Bulk inquiry

Synonym: R-848; R 848; R848; S 28463; S-28463; S28463; VML-600; VML600; VML 600; Resiquimod.

IUPAC/Chemical Name: 1-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

InChi Key: BXNMTOQRYBFHNZ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: CC(O)(C)CN1C(COCC)=NC2=C1C3=CC=CC=C3N=C2N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 314.38218 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x
1. Jiang Y, Huang J, Xu C, Pu K. Activatable polymer nanoagonist for second near-infrared photothermal immunotherapy of cancer. Nat Commun. 2021 Feb 2;12(1):742. doi: 10.1038/s41467-021-21047-0. PMID: 33531498; PMCID: PMC7854754.

1: Sabado RL, Pavlick A, Gnjatic S, Cruz CM, Vengco I, Hasan F, Spadaccia M, Darvishian F, Chiriboga L, Holman RM, Escalon J, Muren C, Escano C, Yepes E, Sharpe D, Vasilakos JP, Rolnitzsky L, Goldberg JD, Mandeli J, Adams S, Jungbluth A, Pan L, Venhaus R, Ott PA, Bhardwaj N. Resiquimod as an Immunologic Adjuvant for NY-ESO-1 Protein Vaccination in Patients with High-Risk Melanoma. Cancer Immunol Res. 2015 Jan 29. [Epub ahead of print] PubMed PMID: 25633712.

2: Ramakrishnan S, Annamalai A, Sachan S, Kumar A, Sharma BK, Govindaraj E, Chellappa MM, Dey S, Krishnaswamy N. Synergy of lipopolysaccharide and resiquimod on type I interferon, pro-inflammatory cytokine, Th1 and Th2 response in chicken peripheral blood mononuclear cells. Mol Immunol. 2015 Mar;64(1):177-82. doi: 10.1016/j.molimm.2014.11.013. Epub 2014 Dec 9. PubMed PMID: 25500018.

3: Craft N, Birnbaum R, Quanquin N, Erfe MC, Quant C, Haskell J, Bruhn KW. Topical resiquimod protects against visceral infection with Leishmania infantum chagasi in mice. Clin Vaccine Immunol. 2014 Sep;21(9):1314-22. doi: 10.1128/CVI.00338-14. Epub 2014 Jul 16. PubMed PMID: 25030052; PubMed Central PMCID: PMC4178562.

4: Lee M, Park CS, Lee YR, Im SA, Song S, Lee CK. Resiquimod, a TLR7/8 agonist, promotes differentiation of myeloid-derived suppressor cells into macrophages and dendritic cells. Arch Pharm Res. 2014 Sep;37(9):1234-40. doi: 10.1007/s12272-014-0379-4. Epub 2014 Apr 19. PubMed PMID: 24748512.

5: Mark KE, Spruance S, Kinghorn GR, Sacks SL, Slade HB, Meng TC, Selke S, Magaret A, Wald A. Three phase III randomized controlled trials of topical resiquimod 0.01-percent gel to reduce anogenital herpes recurrences. Antimicrob Agents Chemother. 2014 Sep;58(9):5016-23. doi: 10.1128/AAC.00077-14. Epub 2014 Apr 7. PubMed PMID: 24709264; PubMed Central PMCID: PMC4135828.

6: Zhou CX, Li D, Chen YL, Lu ZJ, Sun P, Cao YM, Bao HF, Fu YF, Li PH, Bai XW, Xie BX, Liu ZX. Resiquimod and polyinosinic-polycytidylic acid formulation with aluminum hydroxide as an adjuvant for foot-and-mouth disease vaccine. BMC Vet Res. 2014 Jan 3;10:2. doi: 10.1186/1746-6148-10-2. PubMed PMID: 24386990; PubMed Central PMCID: PMC3892093.

7: Peine KJ, Gupta G, Brackman DJ, Papenfuss TL, Ainslie KM, Satoskar AR, Bachelder EM. Liposomal resiquimod for the treatment of Leishmania donovani infection. J Antimicrob Chemother. 2014 Jan;69(1):168-75. doi: 10.1093/jac/dkt320. Epub 2013 Aug 16. PubMed PMID: 23956375; PubMed Central PMCID: PMC3861330.

8: Duong AD, Sharma S, Peine KJ, Gupta G, Satoskar AR, Bachelder EM, Wyslouzil BE, Ainslie KM. Electrospray encapsulation of toll-like receptor agonist resiquimod in polymer microparticles for the treatment of visceral leishmaniasis. Mol Pharm. 2013 Mar 4;10(3):1045-55. doi: 10.1021/mp3005098. Epub 2013 Feb 12. PubMed PMID: 23320733; PubMed Central PMCID: PMC3857017.

9: Meyer T, Surber C, French LE, Stockfleth E. Resiquimod, a topical drug for viral skin lesions and skin cancer. Expert Opin Investig Drugs. 2013 Jan;22(1):149-59. doi: 10.1517/13543784.2013.749236. Epub 2012 Dec 4. Review. PubMed PMID: 23205468.

10: Hackstein H, Knoche A, Nockher A, Poeling J, Kubin T, Jurk M, Vollmer J, Bein G. The TLR7/8 ligand resiquimod targets monocyte-derived dendritic cell differentiation via TLR8 and augments functional dendritic cell generation. Cell Immunol. 2011;271(2):401-12. doi: 10.1016/j.cellimm.2011.08.008. Epub 2011 Aug 22. PubMed PMID: 21889130.

11: Wang YY, Liu S, Lian F, Yang WG, Xue S. Toll-like receptor 7/8 agonist resiquimod induces late preconditioning in neonatal cardiac myocytes. Acta Pharmacol Sin. 2011 May;32(5):565-72. doi: 10.1038/aps.2011.6. Epub 2011 Apr 25. PubMed PMID: 21516132; PubMed Central PMCID: PMC4002520.

12: Ahmad G, Zhang W, Torben W, Noor Z, Siddiqui AA. Protective effects of Sm-p80 in the presence of resiquimod as an adjuvant against challenge infection with Schistosoma mansoni in mice. Int J Infect Dis. 2010 Sep;14(9):e781-7. doi: 10.1016/j.ijid.2010.02.2266. Epub 2010 Jul 13. PubMed PMID: 20630783; PubMed Central PMCID: PMC2941550.

13: Igartua M, Pedraz JL. Topical resiquimod: a promising adjuvant for vaccine development? Expert Rev Vaccines. 2010 Jan;9(1):23-7. doi: 10.1586/erv.09.135. PubMed PMID: 20021302.

14: Chang BA, Cross JL, Najar HM, Dutz JP. Topical resiquimod promotes priming of CTL to parenteral antigens. Vaccine. 2009 Sep 25;27(42):5791-9. doi: 10.1016/j.vaccine.2009.07.062. Epub 2009 Aug 4. PubMed PMID: 19660592.

15: Camateros P, Kanagaratham C, Henri J, Sladek R, Hudson TJ, Radzioch D. Modulation of the allergic asthma transcriptome following resiquimod treatment. Physiol Genomics. 2009 Aug 7;38(3):303-18. doi: 10.1152/physiolgenomics.00057.2009. Epub 2009 Jun 2. PubMed PMID: 19491150.

16: Smits EL, Cools N, Lion E, Van Camp K, Ponsaerts P, Berneman ZN, Van Tendeloo VF. The Toll-like receptor 7/8 agonist resiquimod greatly increases the immunostimulatory capacity of human acute myeloid leukemia cells. Cancer Immunol Immunother. 2010 Jan;59(1):35-46. doi: 10.1007/s00262-009-0721-8. Epub 2009 May 16. PubMed PMID: 19449004.

17: Szeimies RM, Bichel J, Ortonne JP, Stockfleth E, Lee J, Meng TC. A phase II dose-ranging study of topical resiquimod to treat actinic keratosis. Br J Dermatol. 2008 Jul;159(1):205-10. doi: 10.1111/j.1365-2133.2008.08615.x. Epub 2008 Jul 1. PubMed PMID: 18476957.

18: Fife KH, Meng TC, Ferris DG, Liu P. Effect of resiquimod 0.01% gel on lesion healing and viral shedding when applied to genital herpes lesions. Antimicrob Agents Chemother. 2008 Feb;52(2):477-82. Epub 2007 Nov 26. PubMed PMID: 18039918; PubMed Central PMCID: PMC2224757.

19: Tomai MA, Miller RL, Lipson KE, Kieper WC, Zarraga IE, Vasilakos JP. Resiquimod and other immune response modifiers as vaccine adjuvants. Expert Rev Vaccines. 2007 Oct;6(5):835-47. Review. PubMed PMID: 17931162.

20: Pockros PJ, Guyader D, Patton H, Tong MJ, Wright T, McHutchison JG, Meng TC. Oral resiquimod in chronic HCV infection: safety and efficacy in 2 placebo-controlled, double-blind phase IIa studies. J Hepatol. 2007 Aug;47(2):174-82. Epub 2007 May 4. PubMed PMID: 17532523.

Resiquimod

100.0mg / USD 150.0


Additional Information

Resiquimod (R-848) is a drug that acts as an immune response modifier, and has antiviral and antitumour activity. It is used as a topical cream in the treatment of skin lesions such as those caused by herpes simplex virus, and as an adjuvant to increase the effectiveness of vaccines. It has several mechanisms of action, being both an agonist for toll-like receptor 7 and 8, and an upregulator of the opioid growth factor receptor.  (source: http://en.wikipedia.org/wiki/Resiquimod).