From Wikipedia, the free encyclopedia
Chemical compound
AM-6545
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 InfoCard
100.216.518
Formula C 26 H 23 Cl 2 N 5 O 3 S
Molar mass 556.46 g·mol−1 3D model (
JSmol )
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)
Y Key:XBHQLFVDGLPBCK-UHFFFAOYSA-N
Y
N Y
(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rimonabant have been marketed for this application, but have subsequently been withdrawn from sale because of centrally mediated side effects such as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
^ 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 .
^ 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 .
^ 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 .
^ 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 .
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)