AM-6545

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
AM-6545
AM-6545.svg
Systematic (IUPAC) name
5-(4-[4-cyanobut-1-ynyl]phenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1,1-dioxo-thiomorpholino)-1H-pyrazole-3-carboxamide
Identifiers
CAS Number 1245626-05-4 N
PubChem CID: 46912919
ChemSpider 26333263 YesY
Chemical data
Formula C26H23Cl2N5O3S
Molecular mass 556.463 g/mol
  • O=S4(=O)CCN(CC4)NC(=O)c1nn(-c2ccc(Cl)cc2Cl)c(c1C)-c3ccc(C#CCCC#N)cc3
  • 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) YesY
  • Key:XBHQLFVDGLPBCK-UHFFFAOYSA-N YesY
 NYesY (what is this?)

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 Other cannabinoid antagonists such as rimonabant have been marketed for this application, but have subsequently been withdrawn from sale because of centrally mediated side effects such as depression and nausea.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]

See also

References

  1. Lua error in package.lua at line 80: module 'strict' not found. PMID 20664173
  2. Randall PA, Vemuri VK, Segovia KN, Torres EF, Hosmer S, Nunes EJ, Santerre JL, Makriyannis A, Salamone JD. The novel cannabinoid CB1 antagonist AM6545 suppresses food intake and food-reinforced behavior. Pharmacology, Biochemistry and Behavior. 2010 Nov;97(1):179-84. 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. 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. 2010 Oct;161(3):629-42. PMID 20880401
  4. Järbe TU, LeMay BJ, Vemuri VK, Vadivel SK, Zvonok A, Makriyannis A. Central mediation and differential blockade by cannabinergics of the discriminative stimulus effects of the cannabinoid CB1 receptor antagonist rimonabant in rats. Psychopharmacology (Berlin). 2011 Aug;216(3):355-65. PMID 21369753