AZ-11713908

AZ-11713908
Identifiers
	IUPAC name N-(1-(cyclohexylmethyl)-2-((5-ethoxypyridin-2-yl)methyl)-1H-benzo[d]imidazol-5-yl)-N-methylthiophene-2-sulfonamide;
CAS Number	1309682-69-6 ;
ChemSpider	26286889 ;
UNII	MN7RR3VQL7;
Chemical and physical data
Formula	C27H32N4O3S2
Molar mass	524.70 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c5ccsc5S(=O)(=O)N(C)c3ccc1c(c3)nc(Cc(cc2)ncc2OCC)n1CC4CCCCC4;
	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 ; Key:YIEVWZCZMDYKQH-UHFFFAOYSA-N ;
	(what is this?)

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] Many related benzimidazole-derived cannabinoid ligands are known.^[2]^[3]^[4]^[5]

References

^ 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. S2CID 27731273.
^ 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.
^ 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.
^ 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
^ 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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[pmid20696525-1] 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. S2CID 27731273.

[pmid18394887-2] 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.

[pmid18522867-3] 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.

[WO_2004/108688-4] 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

[WO_2004/108712-5] 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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[2]

[3]

[4]

[5]

AZ-11713908

See also

References

zproxy.org

Identifiers

IUPAC name N-(1-(cyclohexylmethyl)-2-((5-ethoxypyridin-2-yl)methyl)-1H-benzo[d]imidazol-5-yl)-N-methylthiophene-2-sulfonamide
CAS Number	1309682-69-6^N
ChemSpider	26286889^Y
UNII	MN7RR3VQL7
Chemical and physical data
Formula	C₂₇H₃₂N₄O₃S₂
Molar mass	524.70 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c5ccsc5S(=O)(=O)N(C)c3ccc1c(c3)nc(Cc(cc2)ncc2OCC)n1CC4CCCCC4
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
^NY (what is this?)