AM-6545

AM-6545 is a drug which acts as a peripherally selective silent antagonist for the CB1 receptor, and was developed for the treatment of obesity. Other cannabinoid antagonists such as rimonabant have been marketed for this application, but have subsequently been withdrawn from sale because of centrally mediated side effects such as depression and nausea.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.[1][2][3][4]

AM-6545
Identifiers
IUPAC name
  • 5-(4-[4-cyanobut-1-ynyl]phenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1,1-dioxo-thiomorpholino)-1H-pyrazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.216.518
Chemical and physical data
FormulaC26H23Cl2N5O3S
Molar mass556.46 g·mol−1
3D model (JSmol)
SMILES
  • O=S4(=O)CCN(CC4)NC(=O)c1nn(-c2ccc(Cl)cc2Cl)c(c1C)-c3ccc(C#CCCC#N)cc3
InChI
  • InChI=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) Y
  • Key:XBHQLFVDGLPBCK-UHFFFAOYSA-N Y
 NY (what is this?)

See also

References
  1. 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 (August 2010). "Peripheral CB1 cannabinoid receptor blockade improves cardiometabolic risk in mouse models of obesity". The Journal of Clinical Investigation. 120 (8): 2953–66. doi:10.1172/JCI42551. PMC 2912197. PMID 20664173.
  2. Randall PA, Vemuri VK, Segovia KN, Torres EF, Hosmer S, Nunes EJ, Santerre JL, Makriyannis A, Salamone JD (November 2010). "The novel cannabinoid CB1 antagonist AM6545 suppresses food intake and food-reinforced behavior". Pharmacology Biochemistry and Behavior. 97 (1): 179–84. doi:10.1016/j.pbb.2010.07.021. PMC 3522179. PMID 20713079.
  3. Cluny NL, Vemuri VK, Chambers AP, Limebeer CL, Bedard H, Wood JT, Lutz B, Zimmer A, Parker LA, Makriyannis A, Sharkey KA (October 2010). "A novel peripherally restricted cannabinoid receptor antagonist, AM6545, reduces food intake and body weight, but does not cause malaise, in rodents". British Journal of Pharmacology. 161 (3): 629–42. doi:10.1111/j.1476-5381.2010.00908.x. PMC 2990160. PMID 20880401.
  4. Järbe TU, LeMay BJ, Vemuri VK, Vadivel SK, Zvonok A, Makriyannis A (August 2011). "Central mediation and differential blockade by cannabinergics of the discriminative stimulus effects of the cannabinoid CB1 receptor antagonist rimonabant in rats". Psychopharmacology. 216 (3): 355–65. doi:10.1007/s00213-011-2226-3. PMC 3727221. PMID 21369753.
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