View source for AM-6545

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid =
| IUPAC_name = 5-(4-[4-cyanobut-1-ynyl]phenyl)-1-(2,4-dichlorophenyl)-4-methyl-''N''-(1,1-dioxo-thiomorpholino)-1''H''-pyrazole-3-carboxamide
| image = AM-6545.svg
| width = 275
<!--Clinical data-->
| pregnancy_category =
| legal_status =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1245626-05-4
| ATC_prefix =
| ATC_suffix =
| PubChem = 46912919
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26333263
| ChEBI = 231613
|  StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H23Cl2N5O3S/c1-18-24(26(34)31-32-13-15-37(35,36)16-14-32)30-33(23-11-10-21(27)17-22(23)28)25(18)20-8-6-19(7-9-20)5-3-2-4-12-29/h6-11,17H,2,4,13-16H2,1H3,(H,31,34)
|  StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XBHQLFVDGLPBCK-UHFFFAOYSA-N
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
<!--Chemical data-->
| C=26|H=23|Cl=2|N=5|O=3|S=1
| smiles = O=S4(=O)CCN(CC4)NC(=O)c1nn(-c2ccc(Cl)cc2Cl)c(c1C)-c3ccc(C#CCCC#N)cc3
}}
'''AM-6545''' is a drug which acts as a peripherally selective [[silent antagonist]] for the [[Cannabinoid receptor 1|CB<sub>1</sub>]] [[Receptor (biochemistry)|receptor]], and was developed for the treatment of [[obesity]]. Other [[cannabinoid antagonist]]s such as [[rimonabant]] have been marketed for this application, but have subsequently been withdrawn from sale because of centrally mediated side effects such as [[depression (mood)|depression]] and [[nausea]]. Because AM-6545 does not cross the [[blood–brain barrier]] to any significant extent, it does not produce these kinds of side effects, but has still been shown to effectively reduce appetite and food consumption in animal studies.<ref>{{cite journal | vauthors = Tam J, Vemuri VK, Liu J, Bátkai S, Mukhopadhyay B, Godlewski G, Osei-Hyiaman D, Ohnuma S, Ambudkar SV, Pickel J, Makriyannis A, Kunos G | title = Peripheral CB1 cannabinoid receptor blockade improves cardiometabolic risk in mouse models of obesity | journal = The Journal of Clinical Investigation | volume = 120 | issue = 8 | pages = 2953–66 | date = August 2010 | pmid = 20664173 | pmc = 2912197 | doi = 10.1172/JCI42551 }}</ref><ref>{{cite journal|authorlink8=Alexandros Makriyannis | vauthors = Randall PA, Vemuri VK, Segovia KN, Torres EF, Hosmer S, Nunes EJ, Santerre JL, Makriyannis A, Salamone JD | title = The novel cannabinoid CB1 antagonist AM6545 suppresses food intake and food-reinforced behavior | journal = Pharmacology Biochemistry and Behavior | volume = 97 | issue = 1 | pages = 179–84 | date = November 2010 | pmid = 20713079 | pmc = 3522179 | doi = 10.1016/j.pbb.2010.07.021 }}</ref><ref>{{cite journal | vauthors = Cluny NL, Vemuri VK, Chambers AP, Limebeer CL, Bedard H, Wood JT, Lutz B, Zimmer A, Parker LA, Makriyannis A, Sharkey KA | title = A novel peripherally restricted cannabinoid receptor antagonist, AM6545, reduces food intake and body weight, but does not cause malaise, in rodents | journal = British Journal of Pharmacology | volume = 161 | issue = 3 | pages = 629–42 | date = October 2010 | pmid = 20880401 | pmc = 2990160 | doi = 10.1111/j.1476-5381.2010.00908.x }}</ref><ref>{{cite journal | vauthors = Järbe TU, LeMay BJ, Vemuri VK, Vadivel SK, Zvonok A, Makriyannis A | title = Central mediation and differential blockade by cannabinergics of the discriminative stimulus effects of the cannabinoid CB1 receptor antagonist rimonabant in rats | journal = Psychopharmacology | volume = 216 | issue = 3 | pages = 355–65 | date = August 2011 | pmid = 21369753 | pmc = 3727221 | doi = 10.1007/s00213-011-2226-3 }}</ref>
== See also ==
* [[CB-13]] – a peripherally selective cannabinoid agonist
* [[O-2050]] – a centrally active CB<sub>1</sub> silent antagonist
* [[Methylnaltrexone]] – a peripherally selective [[mu opioid receptor]] antagonist
* [[TM-38837]] - another peripherally selective cannabinoid antagonist
== References ==
{{reflist}}
{{Cannabinoids}}
[[Category:AM cannabinoids]]
[[Category:CB1 receptor antagonists]]
[[Category:Peripherally selective drugs]]