SX-3228

SX-3228 is a sedative and hypnotic drug used in scientific research. It has similar effects to sedative-hypnotic benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine hypnotic.

SX-3228
Clinical data
Other names5,6,7,8-tetrahydro-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-6-(phenylmethyl)-1,6-naphthyridin-2(1H)-one
Identifiers
IUPAC name
  • (3E)-6-benzyl-3-(5-methoxy-1,3,4-oxadiazol-2(3H)-ylidene)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(3H)-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H18N4O3
Molar mass338.367 g·mol−1
3D model (JSmol)
SMILES
  • COc1nnc(o1)C/3=C/C=4CN(Cc2ccccc2)CCC=4NC\3=O
InChI
  • InChI=1S/C18H18N4O3/c1-24-18-21-20-17(25-18)14-9-13-11-22(8-7-15(13)19-16(14)23)10-12-5-3-2-4-6-12/h2-6,9H,7-8,10-11H2,1H3,(H,19,23) Y
  • Key:BZLLVTYOOJNQIF-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

SX-3228 is a subtype-selective GABAA positive allosteric modulator acting primarily at the α1 subtype. It thus has similar effects to other α1-selective drugs such as zolpidem and zaleplon in animal studies.[1][2] It only partly substitutes for ethanol, and is a strong sedative-hypnotic with only limited anxiolytic effects which appear only at doses that also produce significant sedation.[3][4]

References
  1. Sanger DJ (August 1997). "The effects of new hypnotic drugs in rats trained to discriminate ethanol". Behavioural Pharmacology. 8 (4): 287–92. doi:10.1097/00008877-199708000-00002. PMID 9832988. S2CID 42758930.
  2. Griebel G, Perrault G, Tan S, Schoemaker H, Sanger DJ (September 1999). "Comparison of the pharmacological properties of classical and novel BZ-omega receptor ligands". Behavioural Pharmacology. 10 (5): 483–95. doi:10.1097/00008877-199909000-00007. PMID 10780255.
  3. Griebel G, Perrault G, Sanger DJ (1998). "Limited anxiolytic-like effects of non-benzodiazepine hypnotics in rodents". Journal of Psychopharmacology. 12 (4): 356–65. doi:10.1177/026988119801200405. PMID 10065909. S2CID 269304.
  4. Alvariño F, Monti JM, Jantos H, Monti D (August 1999). "Effect of SX-3228, a selective ligand for the BZ1 receptor, on sleep and waking during the light-dark cycle in the rat". Brazilian Journal of Medical and Biological Research. 32 (8): 1007–14. doi:10.1590/s0100-879x1999000800011. PMID 10454763.
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