Misplaced Pages

AM-6545

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Chemical compound Pharmaceutical compound
AM-6545
Identifiers
IUPAC name
  • 5-(4-phenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1,1-dioxo-thiomorpholino)-1H-pyrazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.216.518 Edit this at Wikidata
Chemical and physical data
FormulaC26H23Cl2N5O3S
Molar mass556.46 g·mol
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)
  • Key:XBHQLFVDGLPBCK-UHFFFAOYSA-N
  (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 Other cannabinoid antagonists such as rimonabant have been marketed for this application, but have subsequently been withdrawn from sale because of centrally mediated side effects such as depression and nausea.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.

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.
Cannabinoids
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
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Categories:
AM-6545 Add topic