Resiquimod

Last updated
Resiquimod
Resiquimod.svg
Clinical data
Routes of
administration 		Topical
ATC code
  • none
Legal status
Legal status
  • Investigational
Identifiers
  • 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H22N4O2
Molar mass 314.389 g·mol−1
3D model (JSmol)
  • CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O
  • 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) X mark.svgN
  • Key:BXNMTOQRYBFHNZ-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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 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, [5] and as an adjuvant to increase the effectiveness of vaccines. [6] In an animal disease model, systemic administration of resiquimod-loaded nanoparticles has been shown to improve response rates to cancer immunotherapy with a checkpoint inhibitor through stimulation of tumor-associated macrophages. [7] It has several mechanisms of action, being both an agonist for toll-like receptor 7 and 8, [8] and an upregulator of the opioid growth factor receptor. [9] On 28 April 2016, orphan designation (EU/3/16/1653) was granted by the European Commission to Galderma R&D, France for resiquimod to be used in the treatment of cutaneous T-cell lymphoma. [10]

See also

References

  1. ↑ Patents #5, 939, 090 and 6, 365, 166
  2. ↑ Szeimies RM, Bichel J, Ortonne JP, Stockfleth E, Lee J, Meng TC (July 2008). "A phase II dose-ranging study of topical resiquimod to treat actinic keratosis". The British Journal of Dermatology. 159 (1): 205–210. doi:10.1111/j.1365-2133.2008.08615.x. PMID   18476957. S2CID   205257237.
  3. ↑ Wu JJ, Huang DB, Tyring SK (November 2004). "Resiquimod: a new immune response modifier with potential as a vaccine adjuvant for Th1 immune responses". Antiviral Research. 64 (2): 79–83. doi:10.1016/j.antiviral.2004.07.002. PMID   15498602.
  4. ↑ Fife KH, Meng TC, Ferris DG, Liu P (February 2008). "Effect of resiquimod 0.01% gel on lesion healing and viral shedding when applied to genital herpes lesions". Antimicrobial Agents and Chemotherapy. 52 (2): 477–482. doi:10.1128/AAC.01173-07. PMC   2224757 . PMID   18039918.
  5. ↑ Rook AH, Gelfand JM, Wysocka M, Troxel AB, Benoit B, Surber C, et al. (September 2015). "Topical resiquimod can induce disease regression and enhance T-cell effector functions in cutaneous T-cell lymphoma". Blood. 126 (12): 1452–1461. doi:10.1182/blood-2015-02-630335. PMC   4573868 . PMID   26228486.
  6. ↑ Tomai MA, Miller RL, Lipson KE, Kieper WC, Zarraga IE, Vasilakos JP (October 2007). "Resiquimod and other immune response modifiers as vaccine adjuvants". Expert Review of Vaccines. 6 (5): 835–847. doi:10.1586/14760584.6.5.835. PMID   17931162. S2CID   30401602.
  7. ↑ Rodell CB, Arlauckas SP, Cuccarese MF, Garris CS, Li R, Ahmed MS, et al. (August 2018). "TLR7/8-agonist-loaded nanoparticles promote the polarization of tumour-associated macrophages to enhance cancer immunotherapy". Nature Biomedical Engineering. 2 (8): 578–588. doi:10.1038/s41551-018-0236-8. PMC   6192054 . PMID   31015631.
  8. ↑ Hurst J, Prinz N, Lorenz M, Bauer S, Chapman J, Lackner KJ, von Landenberg P (February 2009). "TLR7 and TLR8 ligands and antiphospholipid antibodies show synergistic effects on the induction of IL-1beta and caspase-1 in monocytes and dendritic cells". Immunobiology. 214 (8): 683–691. doi:10.1016/j.imbio.2008.12.003. PMID   19249118.
  9. ↑ Zagon IS, Donahue RN, Rogosnitzky M, McLaughlin PJ (August 2008). "Imiquimod upregulates the opioid growth factor receptor to inhibit cell proliferation independent of immune function". Experimental Biology and Medicine. 233 (8): 968–979. doi:10.3181/0802-RM-58. PMID   18480416. S2CID   35164284.
  10. ↑ Committee for Orphan Medicinal Products (27 May 2016). "Resiquimod for the treatment of cutaneous T-cell lymphoma" (PDF). Public summary of opinion on orphan designation. European Medicines Agency. Archived from the original (PDF) on 3 January 2018. Retrieved 30 December 2017.


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