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AZ-11713908

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AZ-11713908
Identifiers
  • N-(1-(cyclohexylmethyl)-2-((5-ethoxypyridin-2-yl)methyl)-1H-benzo[d]imidazol-5-yl)-N-methylthiophene-2-sulfonamide
Chemical and physical data
FormulaC27H32N4O3S2
Molar mass524.697 g/mol g·mol−1
3D model (JSmol)
  • c5ccsc5S(=O)(=O)N(C)c3ccc1c(c3)nc(Cc(cc2)ncc2OCC)n1CC4CCCCC4

AZ-11713908 is a drug which is a peripherally selective cannabinoid agonist, acting as a potent agonist at the CB1 receptor and a partial agonist at CB2. It has poor blood-brain barrier penetration, and so while it is an effective analgesic in animal tests, it produces only peripheral effects at low doses, with much weaker symptoms of central effects compared to other cannabinoid drugs such as WIN 55,212-2.[1] A large number of related benzimidazole derived cannabinoid ligands are known.[2][3][4]

References

  1. ^ Yu XH, Cao CQ, Martino G, Puma C, Morinville A, St-Onge S, Lessard E, Perkins MN, Laird JM (2010). "A peripherally restricted cannabinoid receptor agonist produces robust anti-nociceptive effects in rodent models of inflammatory and neuropathic pain". Pain. 151 (2): 337–44. doi:10.1016/j.pain.2010.07.019. PMID 20696525. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Verbist BM, De Cleyn MA, Surkyn M, Fraiponts E, Aerssens J, Nijsen MJ, Gijsen HJ (2008). "5-Sulfonyl-benzimidazoles as selective CB2 agonists". Bioorganic & Medicinal Chemistry Letters. 18 (8): 2574–9. doi:10.1016/j.bmcl.2008.03.048. PMID 18394887. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Omura H, Kawai M, Shima A, Iwata Y, Ito F, Masuda T, Ohta A, Makita N, Omoto K, Sugimoto H, Kikuchi A, Iwata H, Ando K (2008). "The SAR studies of novel CB2 selective agonists, benzimidazolone derivatives". Bioorganic & Medicinal Chemistry Letters. 18 (11): 3310–4. doi:10.1016/j.bmcl.2008.04.032. PMID 18440813. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Pagé D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, Wei Z, Woo S, Luo X, Cheng YX, Yang H, Srivastava S, Zhou F, Brown W, Tomaszewski M, Walpole C, Hodzic L, St-Onge S, Godbout C, Salois D, Payza K, Payza K (2008). "Novel benzimidazole derivatives as selective CB2 agonists". Bioorganic & Medicinal Chemistry Letters. 18 (13): 3695–700. doi:10.1016/j.bmcl.2008.05.073. PMID 18522867. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)


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