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'''AZ-11713908''' is a drug developed by [[Astra Zeneca]] which is a peripherally selective [[cannabinoid]] [[agonist]], acting as a potent [[agonist]] at the [[Cannabinoid receptor type 1|CB<sub>1</sub>]] receptor and a [[partial agonist]] at [[Cannabinoid receptor type 2|CB<sub>2</sub>]]. 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]].<ref name="pmid20696525">{{cite journal |author=Yu XH, Cao CQ, Martino G, Puma C, Morinville A, St-Onge S, Lessard E, Perkins MN, Laird JM |title=A peripherally restricted cannabinoid receptor agonist produces robust anti-nociceptive effects in rodent models of inflammatory and neuropathic pain |journal=Pain |volume=151 |issue=2 |pages=337–44 |year=2010 |month=November |pmid=20696525 |doi=10.1016/j.pain.2010.07.019 |url=}}</ref> A large number of related [[benzimidazole]] derived cannabinoid ligands are known.<ref name="pmid18394887">{{cite journal |author=Verbist BM, De Cleyn MA, Surkyn M, Fraiponts E, Aerssens J, Nijsen MJ, Gijsen HJ |title=5-Sulfonyl-benzimidazoles as selective CB2 agonists |journal=Bioorganic & Medicinal Chemistry Letters |volume=18 |issue=8 |pages=2574–9 |year=2008 |month=April |pmid=18394887 |doi=10.1016/j.bmcl.2008.03.048 |url=}}</ref><ref name="pmid18522867">{{cite journal |author=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 |title=Novel benzimidazole derivatives as selective CB2 agonists |journal=Bioorganic & Medicinal Chemistry Letters |volume=18 |issue=13 |pages=3695–700 |year=2008 |month=July |pmid=18522867 |doi=10.1016/j.bmcl.2008.05.073 |url=}}</ref><ref name="WO 2004/108688">{{Ref patent2 | country = WO | number = 2004/108688 | status = granted | title = BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF | pubdate = | gdate = 16.12.2004 | pridate= 09.06.2004 | inventor = LIU Z, PAGÈ D, WALPOLE C, YANG H | assign1= }}</ref><ref name="WO 2004/108712">{{Ref patent2 | country = WO | number = 2004/108712 | status = granted | title = BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF | pubdate = | gdate = 16.12.2004 | pridate= 09.06.2004 | inventor = LIU Z, PAGÈ D, WALPOLE C, YANG H | assign1= }}</ref>
'''AZ-11713908''' is a drug developed by [[AstraZeneca]] which is a peripherally selective [[cannabinoid]] [[agonist]], acting as a potent [[agonist]] at the [[Cannabinoid receptor type 1|CB<sub>1</sub>]] receptor and a [[partial agonist]] at [[Cannabinoid receptor type 2|CB<sub>2</sub>]]. 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]].<ref name="pmid20696525">{{cite journal |author=Yu XH, Cao CQ, Martino G, Puma C, Morinville A, St-Onge S, Lessard E, Perkins MN, Laird JM |title=A peripherally restricted cannabinoid receptor agonist produces robust anti-nociceptive effects in rodent models of inflammatory and neuropathic pain |journal=Pain |volume=151 |issue=2 |pages=337–44 |year=2010 |month=November |pmid=20696525 |doi=10.1016/j.pain.2010.07.019 |url=}}</ref> A large number of related [[benzimidazole]] derived cannabinoid ligands are known.<ref name="pmid18394887">{{cite journal |author=Verbist BM, De Cleyn MA, Surkyn M, Fraiponts E, Aerssens J, Nijsen MJ, Gijsen HJ |title=5-Sulfonyl-benzimidazoles as selective CB2 agonists |journal=Bioorganic & Medicinal Chemistry Letters |volume=18 |issue=8 |pages=2574–9 |year=2008 |month=April |pmid=18394887 |doi=10.1016/j.bmcl.2008.03.048 |url=}}</ref><ref name="pmid18522867">{{cite journal |author=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 |title=Novel benzimidazole derivatives as selective CB2 agonists |journal=Bioorganic & Medicinal Chemistry Letters |volume=18 |issue=13 |pages=3695–700 |year=2008 |month=July |pmid=18522867 |doi=10.1016/j.bmcl.2008.05.073 |url=}}</ref><ref name="WO 2004/108688">{{Ref patent2 | country = WO | number = 2004/108688 | status = granted | title = BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF | pubdate = | gdate = 16.12.2004 | pridate= 09.06.2004 | inventor = LIU Z, PAGÈ D, WALPOLE C, YANG H | assign1= }}</ref><ref name="WO 2004/108712">{{Ref patent2 | country = WO | number = 2004/108712 | status = granted | title = BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF | pubdate = | gdate = 16.12.2004 | pridate= 09.06.2004 | inventor = LIU Z, PAGÈ D, WALPOLE C, YANG H | assign1= }}</ref>


==See also==
==See also==

Revision as of 01:02, 3 October 2011

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 developed by AstraZeneca 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][5]

See also

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. ^ 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)
  4. ^ WO patent 2004/108688, LIU Z, PAGÈ D, WALPOLE C, YANG H, "BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF", granted 16.12.2004 
  5. ^ WO patent 2004/108712, LIU Z, PAGÈ D, WALPOLE C, YANG H, "BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF", granted 16.12.2004 


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