From Wikipedia, the free encyclopedia
Chemical compound
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
References
^ 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): 769–776.
doi :
10.1021/jm980363y .
PMID
10052983 .
^ 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): 905–915.
doi :
10.1016/j.neuropharm.2012.06.046 .
PMC
3408547 .
PMID
22771770 .
^ 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): 905–915.
doi :
10.1016/j.neuropharm.2012.06.046 .
PMC
3408547 .
PMID
22771770 .
^ Carpi S, Fogli S, Romanini A, Pellegrino M, Adinolfi B, Podestà A, et al. (August 2015).
"AM251 induces apoptosis and G2/M cell cycle arrest in A375 human melanoma cells" (PDF) . Anti-Cancer Drugs . 26 (7): 754–762.
doi :
10.1097/CAD.0000000000000246 .
hdl :
11568/750318 .
PMID
25974027 .
S2CID
205526223 .
Archived (PDF) from the original on July 2, 2021.
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