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S-777,469

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Chemical compound Pharmaceutical compound
S-777,469
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 1--5-methyl-2-oxopyridine-3-carbonyl]amino]cyclohexane-1-carboxylic acid
CAS Number
PubChem CID
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H27FN2O4
Molar mass414.477 g·mol
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

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.

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.

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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