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TCS-OX2-29

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Orexin antagonist Pharmaceutical compound
TCS-OX2-29
Identifiers
IUPAC name
  • (2S)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-3,3-dimethyl-2-(pyridin-4-ylmethylamino)butan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H31N3O3
Molar mass397.519 g·mol
3D model (JSmol)
SMILES
  • c3cnccc3CNC(C(C)(C)C)C(=O)N(Cc2cc1OC)CCc2cc1OC
  (verify)

TCS-OX2-29 is an orexin antagonist. It was the first non-peptide antagonist developed that is selective for the orexin receptor subtype OX2, with an IC50 of 40nM and selectivity of around 250x for OX2 over OX1 receptors. Orexin antagonists are expected to be useful for the treatment of insomnia, with subtype-selective antagonists such as TCS-OX2-29 potentially offering more specificity of action compared to non-selective orexin antagonists like almorexant.

References

  1. Hirose M, Egashira S, Goto Y, Hashihayata T, Ohtake N, Iwaasa H, et al. (December 2003). "N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: the first orexin-2 receptor selective non-peptidic antagonist". Bioorganic & Medicinal Chemistry Letters. 13 (24): 4497–9. doi:10.1016/j.bmcl.2003.08.038. PMID 14643355.
  2. Roecker AJ, Coleman PJ (2008). "Orexin receptor antagonists: medicinal chemistry and therapeutic potential". Current Topics in Medicinal Chemistry. 8 (11): 977–87. doi:10.2174/156802608784936746. PMID 18673167.
Orexin receptor modulators
OX1
OX2
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