S-444,823

S-444,823
Clinical data
ATC code	none;
Identifiers
	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;
CAS Number	885490-15-3 ;
PubChem CID	57387465;
ChemSpider	28501432;
UNII	NVJ8QDQ4QW;
Chemical and physical data
Formula	C25H33N3O4S
Molar mass	471.62 g·mol−1
3D model (JSmol)	Interactive image;
	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]

References

^ Arimura A. Novel Use of Cannabinoid Receptor Agonist. Patent WO 2005/016351
^ Odan M, Ishizuka N, Hiramatsu Y, Inagaki M, Hashizume H, Fujii Y, et al. (April 2012). "Discovery of S-444823, a potent CB1/CB2 dual agonist as an antipruritic agent". Bioorganic & Medicinal Chemistry Letters. 22 (8): 2898–901. doi:10.1016/j.bmcl.2012.02.050. PMID 22421019.

[1] Arimura A. Novel Use of Cannabinoid Receptor Agonist. Patent WO 2005/016351

[pmid22421019-2] Odan M, Ishizuka N, Hiramatsu Y, Inagaki M, Hashizume H, Fujii Y, et al. (April 2012). "Discovery of S-444823, a potent CB1/CB2 dual agonist as an antipruritic agent". Bioorganic & Medicinal Chemistry Letters. 22 (8): 2898–901. doi:10.1016/j.bmcl.2012.02.050. PMID 22421019.

[1]

[2]

See also

References