AZ-11713908

AZ-11713908

Systematic (IUPAC) name
N-(1-(cyclohexylmethyl)-2-((5-ethoxypyridin-2-yl)methyl)-1H-benzo[d]imidazol-5-yl)-N-methylthiophene-2-sulfonamide
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
ATC code	?
ChemSpider	26286889 Y
Chemical data
Formula	C27H32N4O3S2
Mol. mass	524.697 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C27H32N4O3S2/c1-3-34-23-13-11-21(28-18-23)16-26-29-24-17-22(30(2)36(32,33)27-10-7-15-35-27)12-14-25(24)31(26)19-20-8-5-4-6-9-20/h7,10-15,17-18,20H,3-6,8-9,16,19H2,1-2H3 Y Key:YIEVWZCZMDYKQH-UHFFFAOYSA-N Y

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

• AM-6545
• CB-13

References

1. ^ Yu XH, Cao CQ, Martino G, Puma C, Morinville A, St-Onge S, Lessard E, Perkins MN, Laird JM (November 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. 
2. ^ Verbist BM, De Cleyn MA, Surkyn M, Fraiponts E, Aerssens J, Nijsen MJ, Gijsen HJ (April 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. 
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 (July 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. 
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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