AM-251 (drug)

AM-251 (drug)
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	555.238 g/mol g·mol−1
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 SR141716A (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 7.5nM) than SR141716A, which has a K_i value of 11.5nM, AM-251 is, however, about two-fold more selective for the CB₁ receptor when compared to SR141716A.^[1] Like SR141716A, it is additionally a μ-opioid receptor antagonist.^[2]

References

^ Lan, R; Liu, Q; Fan, P; Lin, S; Fernando, SR; McCallion, D; Pertwee, R; Makriyannis, A. "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists". J Med Chem. 42: 769–76. doi:10.1021/jm980363y. PMID 10052983.
^ Seely, KA; Brents, LK; Franks, LN; Rajasekaran, M; Zimmerman, SM; Fantegrossi, WE; Prather, PL (2012). "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies". Neuropharmacology. 63: 905–15. doi:10.1016/j.neuropharm.2012.06.046. PMC 3408547. PMID 22771770.

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[1] Lan, R; Liu, Q; Fan, P; Lin, S; Fernando, SR; McCallion, D; Pertwee, R; Makriyannis, A. "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists". J Med Chem. 42: 769–76. doi:10.1021/jm980363y. PMID 10052983.

[2] Seely, KA; Brents, LK; Franks, LN; Rajasekaran, M; Zimmerman, SM; Fantegrossi, WE; Prather, PL (2012). "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies". Neuropharmacology. 63: 905–15. doi:10.1016/j.neuropharm.2012.06.046. PMC 3408547. PMID 22771770.

[1]

[2]

See also

References