Chemistry:AM-251 (drug)

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Short description: Chemical compound
AM-251
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Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC22H21Cl2IN4O
Molar mass555.24 g·mol−1
3D model (JSmol)
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AM-251 is an inverse agonist at the CB1 cannabinoid receptor. AM-251 is structurally very close to rimonabant; both are biarylpyrazole cannabinoid receptor antagonists. In AM-251, the p-chloro group attached to the phenyl substituent at C-5 of the pyrazole ring is replaced with a p-iodo group. The resulting compound exhibits slightly better binding affinity for the CB1 receptor (with a Ki value of 7.5 nM) than rimonabant, which has a Ki value of 11.5 nM, AM-251 is, however, about two-fold more selective for the CB1 receptor when compared to rimonabant.[1] Like rimonabant, it is additionally a μ-opioid receptor antagonist[2] that attenuates analgesic effects.[3]

AM251 has shown an in vitro antimelanoma activity against pancreatic and colon cancer cells.[4]

See also

  • Discovery and development of Cannabinoid Receptor 1 Antagonists

References

  1. ↑ "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists". Journal of Medicinal Chemistry 42 (4): 769–776. February 1999. doi:10.1021/jm980363y. PMID 10052983. 
  2. ↑ "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies". Neuropharmacology 63 (5): 905–915. October 2012. doi:10.1016/j.neuropharm.2012.06.046. PMID 22771770. 
  3. ↑ "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies". Neuropharmacology 63 (5): 905–915. October 2012. doi:10.1016/j.neuropharm.2012.06.046. PMID 22771770. 
  4. ↑ "AM251 induces apoptosis and G2/M cell cycle arrest in A375 human melanoma cells". Anti-Cancer Drugs 26 (7): 754–762. August 2015. doi:10.1097/CAD.0000000000000246. PMID 25974027. https://arpi.unipi.it/retrieve/handle/11568/750318/395886/Post-Print_2015_Carpi%20Nieri%20Anti-Cancer%20Drugs.pdf. 



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