S-777,469

S-777,469 is a drug developed by Shionogi which is a cannabinoid receptor agonist, with 128x selectivity for the CB2 subtype, having a CB2 affinity of 36nM, and a CB1 affinity over 4600nM.

S-777,469
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 1-[[6-ethyl-1-[(4-fluorophenyl)methyl]-5-methyl-2-oxopyridine-3-carbonyl]amino]cyclohexane-1-carboxylic acid
CAS Number
PubChem CID
UNII
ChEMBL
Chemical and physical data
FormulaC23H27FN2O4
Molar mass414.477 g·mol−1
3D model (JSmol)
SMILES
  • CCC1=C(C=C(C(=O)N1CC2=CC=C(C=C2)F)C(=O)NC3(CCCCC3)C(=O)O)C
InChI
  • InChI=1S/C23H27FN2O4/c1-3-19-15(2)13-18(20(27)25-23(22(29)30)11-5-4-6-12-23)21(28)26(19)14-16-7-9-17(24)10-8-16/h7-10,13H,3-6,11-12,14H2,1-2H3,(H,25,27)(H,29,30)
  • Key:JIYXOJFSPOFZPY-UHFFFAOYSA-N

In animal studies it showed antipruritic effects, and passed Phase II human trials for the treatment of atopic dermatitis, but development was ultimately not continued further.[1][2][3][4]

See also

References
  1. Odan M, Ishizuka N, Hiramatsu Y, Inagaki M, Hashizume H, Fujii Y, et al. (April 2012). "Discovery of S-777469: an orally available CB2 agonist as an antipruritic agent". Bioorganic & Medicinal Chemistry Letters. 22 (8): 2803–6. doi:10.1016/j.bmcl.2012.02.072. PMID 22444677.
  2. Haruna T, Soga M, Morioka Y, Hikita I, Imura K, Furue Y, et al. (2015). "S-777469, a novel cannabinoid type 2 receptor agonist, suppresses itch-associated scratching behavior in rodents through inhibition of itch signal transmission". Pharmacology. 95 (1–2): 95–103. doi:10.1159/000371890. PMID 25721168. S2CID 41617054.
  3. Haruna T, Soga M, Morioka Y, Imura K, Furue Y, Yamamoto M, et al. (2017). "The Inhibitory Effect of S-777469, a Cannabinoid Type 2 Receptor Agonist, on Skin Inflammation in Mice". Pharmacology. 99 (5–6): 259–267. doi:10.1159/000455916. PMID 28214870. S2CID 31692497.
  4. Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC 4927043. PMID 27398024.


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