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AM-251

Identifiers
IUPAC name 1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidyl)pyrazole-3-carboxamide
CAS Number	183232-66-8
PubChem CID	2125
IUPHAR/BPS	3317
ChemSpider	2040
UNII	3I4FA44MAI
ChEBI	CHEBI:90724
ChEMBL	ChEMBL285932
CompTox Dashboard (EPA)	DTXSID7042695
ECHA InfoCard	100.162.062
Chemical and physical data
Formula	C22H21Cl2IN4O
Molar mass	555.24 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(I)cc3)c4C
InChI InChI=1S/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30) Key:BUZAJRPLUGXRAB-UHFFFAOYSA-N
(verify)

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 K_i value of 7.5 nM) than rimonabant, which has a K_i value of 11.5 nM, AM-251 is, however, about two-fold more selective for the CB₁ receptor when compared to rimonabant. Like rimonabant, it is additionally a μ-opioid receptor antagonist that attenuates analgesic effects.

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

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): 769–776. 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): 905–915. doi:10.1016/j.neuropharm.2012.06.046. PMC 3408547. PMID 22771770.
3. 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.
4. 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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• v
• t
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• CB1 receptor antagonists
• 1-Piperidinyl compounds
• Pyrazoles
• Hydrazides
• 4-Iodophenyl compounds
• Chlorobenzene derivatives
• AM cannabinoids
• Pyrazolecarboxamides
• Mu-opioid receptor antagonists
• Antineoplastic drugs
• Cannabinoid stubs