AM-251 (drug)

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]

AM-251
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.162.062
Chemical and physical data
FormulaC22H21Cl2IN4O
Molar mass555.24 g·mol−1
3D model (JSmol)
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See also
  • Discovery and development of Cannabinoid Receptor 1 Antagonists

References
  1. Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, et al. (February 1999). "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists". Journal of Medicinal Chemistry. 42 (4): 769–76. doi:10.1021/jm980363y. PMID 10052983.
  2. Seely KA, Brents LK, Franks LN, Rajasekaran M, Zimmerman SM, Fantegrossi WE, Prather PL (October 2012). "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies". Neuropharmacology. 63 (5): 905–15. doi:10.1016/j.neuropharm.2012.06.046. PMC 3408547. PMID 22771770.
  3. Seely, Kathryn A.; Brents, Lisa K.; Franks, Lirit N.; Rajasekaran, Maheswari; Zimmerman, Sarah M.; Fantegrossi, William E.; Prather, Paul L. (October 2012). "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: Implications for opioid/cannabinoid interaction studies". Neuropharmacology. 63 (5): 905–915. doi:10.1016/j.neuropharm.2012.06.046. PMC 3408547. PMID 22771770.


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