Resiquimod

from Wikipedia, the free encyclopedia
Structural formula
Resiquimod structural formula
General
Non-proprietary name Resiquimod
other names
  • 1- [4-Amino-2- (ethoxymethyl) -1 H -imidazo [4,5- c ] quinolin-1-yl] -2-methylpropan-2-ol ( IUPAC )
  • R848
  • R-848
  • S28463
Molecular formula C 17 H 22 N 4 O 2
Brief description

White dust

External identifiers / databases
CAS number 144875-48-9
PubChem 159603
ChemSpider 140330
DrugBank DB06530
Wikidata Q426054
properties
Molar mass 314.382 g · mol -1
Physical state

firmly

Melting point

166 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Resiquimod (R848) (manufacturer Spirig Pharma ) is a drug from the group of immunomodulators ( immune response modifier , IRM) that is still in development, which is used in the treatment of small, superficial basal cell skin cancer (white skin cancer; basalioma), actinic keratosis , cutaneous T-cell lymphoma and genital warts ( condylomata acuminata ) should be used.

Resiquimod is a low molecular compound (small molecule) .

Clinical information

Application areas (indications)

Resiquimod is currently being tested in a number of indications, primarily for the treatment of actinic keratosis. Even with herpes simplex - virus infections (genital herpes) shows it effect, moreover, the effectiveness as an adjuvant in the treatment of other viral diseases such as hepatitis C studies.

Ongoing studies

Prospective, randomized, partly blinded, partly placebo-controlled, multicenter clinical trial to investigate the appropriate dosage, safety, tolerability and effectiveness of an externally applicable Resiquimod gel in patients with multiple lesions of actinic keratosis.

Mechanism of action (pharmacodynamics)

Resiquimod binds to two toll-like receptors (TLR), i.e. H. to TLR7 and TLR8, and is considered a successor to imiquimod , which has a similar mechanism of action, but only binds to TLR7 and is less effective.

History

Resiquimod was developed by 3M Drug Delivery Systems and out-licensed to the Swiss pharmaceutical company Spirig Pharma AG in 2010.

literature

  • K. Hattermann, S. Picard et al. a .: The Toll-like receptor 7/8-ligand resiquimod (R-848) primes human neutrophils for leukotriene B4, prostaglandin E2 and platelet-activating factor biosynthesis. In: FASEB journal. Volume 21, Number 7, May 2007, pp. 1575-1585, doi: 10.1096 / fj.06-7457com , PMID 17264163 .
  • DH Dockrell, GR Kinghorn: Imiquimod and resiquimod as novel immunomodulators. In: The Journal of antimicrobial chemotherapy. Volume 48, Number 6, December 2001, pp. 751-755. PMID 11733457 (Review).

Individual evidence

  1. ↑ a b Resiquimod data sheet , ≥98% (HPLC) from Sigma-Aldrich , accessed on May 15, 2012 ( PDF ).
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Public summary of opinion on orphan designation Resiquimod for the treatment of cutaneous T-cell lymphoma Committee for Orphan Medicinal Products, of the European Medicines Agency of May 27, 2016
  4. ↑ Gerd Plewig: Advanced training week for practical dermatology and venereology e. V., progress through training 2006. Springer Verlag, 2007, ISBN 978-3-540-30514-9 .
  5. ↑ RM Szeimies, J. Bichel, JP Ortonne, E. Stockfleth, J. Lee, TC Meng: A phase II dose-ranging study of topical resiquimod to treat actinic keratosis. In: Br J Dermatol . 159 (1), 2008 Jul, pp. 205-210. PMID 18476957
  6. ↑ JJ Wu, DB Huang, SK Tyring: Resiquimod: a new immune response modifier with potential as a vaccine adjuvant for Th1 immune responses . In: Antiviral Research . tape 64 , no. 2 , November 2004, p. 79-83 , doi : 10.1016 / j.antiviral.2004.07.002 , PMID 15498602 .
  7. ↑ KH Fife, TC Meng, DG Ferris, P. Liu: Effect of resiquimod 0.01% gel on lesion healing and viral shedding when applied to genital herpes lesions . In: Antimicrobial Agents and Chemotherapy . tape 52 , no. 2 , February 2008, p. 477-482 , doi : 10.1128 / AAC.01173-07 , PMID 18039918 , PMC 2224757 (free full text).
  8. ^ MA Tomai, RL Miller, KE Lipson, WC Kieper, IE Zarraga, JP Vasilakos: Resiquimod and other immune response modifiers as vaccine adjuvants . In: Expert Review of Vaccines . tape 6 , no. 5 , October 2007, p. 835-847 , doi : 10.1586 / 14760584.6.5.835 , PMID 17931162 .
  9. ↑ Development status of compounds that target TLRs for viral and bacterial infections, Targeting Toll-like receptors: emerging therapeutics? In: Nature Reviews Drug Discovery . 9, April 2010, pp. 293-307. doi: 10.1038 / nrd3203
  10. ↑ Germany - BfArM, 2011-003943-23, Spirig Pharma AG WebSite: EU Clinical Trials Register (English).
  11. ↑ Peter Fritsch: Dermatology and Venereology. 2nd Edition. Springer Verlag, 2004, ISBN 3-540-00332-0 .
  12. ↑ 3M Drug Delivery Systems Signs Agreement with Spirig Pharma AG. Press release from 3M Drug Delivery Systems dated December 16, 2010.