Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
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| tradename =
| tradename =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 1309682-69-6
| CAS_number = 1309682-69-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MN7RR3VQL7
| PubChem =
| PubChem =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26286889
| ChemSpiderID = 26286889
| InChI = 1/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
| InChIKey = YIEVWZCZMDYKQH-UHFFFAOYAA
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
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<!--Chemical data-->
<!--Chemical data-->
| C=27 | H=32 | N=4 | O=3 | S=2
| C=27 | H=32 | N=4 | O=3 | S=2
| molecular_weight = 524.697 g/mol
| smiles = c5ccsc5S(=O)(=O)N(C)c3ccc1c(c3)nc(Cc(cc2)ncc2OCC)n1CC4CCCCC4
| smiles = 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 [[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 |date=November 2010 |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 |date=April 2008 |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 |date=July 2008 |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 |vauthors=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 |date=November 2010 |pmid=20696525 |doi=10.1016/j.pain.2010.07.019 |s2cid=27731273 }}</ref> Many related [[benzimidazole]]-derived cannabinoid ligands are known.<ref name="pmid18394887">{{cite journal |vauthors=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 |date=April 2008 |pmid=18394887 |doi=10.1016/j.bmcl.2008.03.048 }}</ref><ref name="pmid18522867">{{cite journal |vauthors=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 |date=July 2008 |pmid=18522867 |doi=10.1016/j.bmcl.2008.05.073 }}</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==
* [[AM-6545]]
* [[AM-6545]]
* [[AZD-1940]]
* [[CB-13]]
* [[CB-13]]
* [[RQ-00202730]]


==References==
==References==
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{{Cannabinoids}}
{{Cannabinoids}}
⚫
{{cannabinoid-stub}}


[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Benzimidazoles]]
[[Category:Benzimidazoles]]
[[Category:Peripherally selective drugs]]
[[Category:Peripherally selective drugs]]


⚫
{{cannabinoid-stub}}

Latest revision as of 18:42, 6 September 2022

AZ-11713908
Identifiers
  • N-(1-(cyclohexylmethyl)-2-((5-ethoxypyridin-2-yl)methyl)-1H-benzo[d]imidazol-5-yl)-N-methylthiophene-2-sulfonamide
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC27H32N4O3S2
Molar mass524.70 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 checkY
  • Key:YIEVWZCZMDYKQH-UHFFFAOYSA-N checkY
 ☒NcheckY (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[edit]

References[edit]

  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.
  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 


source: https://en.wikipedia.org/w/index.php?title=AZ-11713908&diff=1108874016&oldid=699636068

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