Gaboxadol

Gaboxadol
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3(2H)-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.059.039 Edit this at Wikidata
Chemical and physical data
FormulaC6H8N2O2
Molar mass140.142 g·mol−1
3D model (JSmol)
SMILES
  • O=C1/C2=C(\ON1)CNCC2
InChI
  • InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9) checkY
  • Key:ZXRVKCBLGJOCEE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Gaboxadol, also known as 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol (THIP), is a conformationally constrained derivative of the alkaloid muscimol that was first synthesized in 1977 by the Danish chemist Povl Krogsgaard-Larsen.[1] In the early 1980s gaboxadol was the subject of a series of pilot studies that tested its efficacy as an analgesic and anxiolytic, as well as a treatment for tardive dyskinesia, Huntington's disease, Alzheimer's disease, and spasticity.[1] It was not until 1996 that researchers attempted to harness gaboxadol's frequently reported sedative "adverse effect" for the treatment of insomnia, resulting in a series of clinical trials sponsored by Lundbeck and Merck.[1][2] In March, 2007, Merck and Lundbeck cancelled work on the drug, citing safety concerns and the failure of an efficacy trial. It acts on the GABA system, but in a different way from benzodiazepines, Z-Drugs, and barbiturates. Lundbeck states that gaboxadol also increases deep sleep (stage 4). It is, however, not reinforcing like benzodiazepines are.[3]

In 2015, Lundbeck sold its rights to the molecule to Ovid Therapeutics, whose plan is to develop it for FXS and Angelman syndrome.[4] It is known internally in Ovid as OV101.

See also

References

  1. 1 2 3 Morris H (August 2013). "Gaboxadol". Harper's Magazine. August 2013. Retrieved 2014-11-20.
  2. ↑ US Patent 4278676 - Heterocyclic compounds
  3. ↑ Vashchinkina E, Panhelainen A, Vekovischeva OY, Aitta-aho T, Ebert B, Ator NA, Korpi ER (April 2012). "GABA site agonist gaboxadol induces addiction-predicting persistent changes in ventral tegmental area dopamine neurons but is not rewarding in mice or baboons". The Journal of Neuroscience. 32 (15): 5310–20. doi:10.1523/JNEUROSCI.4697-11.2012. PMC 6622081. PMID 22496576.
  4. ↑ Tirrell M (16 April 2015). "Former Teva CEO's new gig at Ovid Therapeutics". CNBC. Retrieved 2015-05-06.
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