SCH 336 - CAS 447459-51-0
Category: Inhibitor
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Molecular Formula:
C23H25NO8S3
Molecular Weight:
539.64
COA:
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Targets:
Cannabinoid Receptor
Description:
SCH 336 is a potent and selective CB2 receptor inverse agonist (Ki = 1.8 nM, EC50 = 2 nM) with 100-fold selectivity over CB1. SCH 336 has been shown to increase forskolin stimulated cAMP accumulation in CHO cells expressing human CB2 receptors. It inhibits leukocyte migration in a murine model of delayed-type hypersensitivity and suppresses antigen-induced lung eosinophilia in a mouse allergy model.
Brife Description:
CB2 receptor inverse agonist
Purity:
≥98% by HPLC
Synonyms:
SCH-336; SCH 336; SCH336. N-[(1S)-1-[4-[[4-Methoxy-2-[(4-methoxyphenyl)sulfonyl]phenyl]sulfonyl]phenyl]ethyl]methanesulfonamide
MSDS:
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InChIKey:
NXODIUKWAVUFGF-INIZCTEOSA-N
InChI:
InChI=1S/C23H25NO8S3/c1-16(24-33(4,25)26)17-5-10-20(11-6-17)34(27,28)22-14-9-19(32-3)15-23(22)35(29,30)21-12-7-18(31-2)8-13-21/h5-16,24H,1-4H3/t16-/m0/s1
Canonical SMILES:
CC(C1=CC=C(C=C1)S(=O)(=O)C2=C(C=C(C=C2)OC)S(=O)(=O)C3=CC=C(C=C3)OC)NS(=O)(=O)C
1.A novel cannabinoid peripheral cannabinoid receptor-selective inverse agonist blocks leukocyte recruitment in vivo.
Lunn CA;Fine JS;Rojas-Triana A;Jackson JV;Fan X;Kung TT;Gonsiorek W;Schwarz MA;Lavey B;Kozlowski JA;Narula SK;Lundell DJ;Hipkin RW;Bober LA J Pharmacol Exp Ther. 2006 Feb;316(2):780-8. Epub 2005 Oct 28.
The expression of the cannabinoid peripheral cannabinoid receptor (CB(2)) receptor on peripheral immune cells suggests that compounds specific for CB(2) might be effective anti-inflammatory agents. In this report, we present the initial biological profiling of a novel triaryl bis-sulfone, Sch.336 (N-[1(S)-[4-[[4-methoxy-2-[(4-methoxyphenyl)sulfonyl]phenyl]-sulfonyl]phenyl]ethyl]methanesulfonamide), which is selective for the human cannabinoid CB(2) receptor (hCB(2)). Sch.336 is an inverse agonist at hCB(2), as shown by its ability to decrease guanosine 5'-3-O-(thio)triphosphate (GTPgammaS) binding to membranes containing hCB(2), by the ability of GTPgammaS to left-shift Sch.336 binding to hCB(2) in these membranes, and by the compound's ability to increase forskolin-stimulated cAMP levels in CHO cells expressing hCB(2). In these systems, Sch.336 displays a greater potency than that reported for the CB(2)-selective dihydropyrazole, SR144528 (N-[(1S)-endo-1,3,3-trimethylbicyclo [2.2.1]heptan2-yl]-5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-1H-pyrazole-3-carboxamide). In vitro, Sch.336 impairs the migration of CB(2)-expressing recombinant cell lines to the cannabinoid agonist 2-arachidonylglycerol.
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CAS 447459-51-0 SCH 336

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