S-444,823

S-444,823

Systematic (IUPAC) name
3-(2-(1-(cyclohexylmethyl)-2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamido)thiazol-4-yl)propanoic acid
Clinical data
Legal status	?
Identifiers
CAS Number	885490-15-3
ATC code	none
ChemSpider	28501432
Chemical data
Formula	C25H33N3O4S
Molar mass	471.61 g/mol
SMILES O=C(C(C(NC1=NC(CCC(O)=O)=CS1)=O)=C2)N(CC3CCCCC3)C4=C2CCCCCC4
InChI InChI=1S/C25H33N3O4S/c29-22(30)13-12-19-16-33-25(26-19)27-23(31)20-14-18-10-6-1-2-7-11-21(18)28(24(20)32)15-17-8-4-3-5-9-17/h14,16-17H,1-13,15H2,(H,29,30)(H,26,27,31) Key:SYBONVBDFTYUQP-UHFFFAOYSA-N

S-444,823 is a drug developed by Shionogi which is a cannabinoid agonist.^[1] It was developed as an antipruritic, and has moderate selectivity for the CB₂ subtype, having a CB₂ affinity of 18nM, and 32x selectivity over the CB₁ receptor. In animal studies it showed analgesic effects and strongly reduced itching responses, but without producing side effects such as sedation and catalepsy that are seen with centrally acting CB₁ agonists.^[2]

See also

• JTE 7-31

References

1. Arimura A. Novel Use of Cannabinoid Receptor Agonist. Patent WO 2005/016351
2. Odan M, et al. Discovery of S-444823, a potent CB1/CB2 dual agonist as an antipruritic agent. Bioorganic and Medicinal Chemistry Letters. 2012 Apr 15;22(8):2898-901. PMID 22421019