From Wikipedia, the free encyclopedia
Chemical compound
AZ-11713908
N-(1-(cyclohexylmethyl)-2-((5-ethoxypyridin-2-yl)methyl)-1H-benzo[d]imidazol-5-yl)-N-methylthiophene-2-sulfonamide
CAS Number
ChemSpider
UNII
Formula C 27 H 32 N 4 O 3 S 2
Molar mass 524.70 g·mol−1 3D model (
JSmol )
c5ccsc5S(=O)(=O)N(C)c3ccc1c(c3)nc(Cc(cc2)ncc2OCC)n1CC4CCCCC4
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
N Y
(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]
See also
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
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)