Iso-THIP

Iso-THIP
Clinical data
Other namesIsoTHIP; Isogaboxadol
Drug classGABAA-ρ receptor antagonist; GABAA receptor antagonist
ATC code
  • None
Identifiers
  • 4,5,6,7-tetrahydro-1H-[1,2]oxazolo[3,4-c]pyridin-3-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC6H8N2O2
Molar mass140.142 g·mol−1
3D model (JSmol)
  • C1CNCC2=C1C(=O)ON2
  • InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)8-10-6/h7-8H,1-3H2
  • Key:HTKHYLOBQZWEFD-UHFFFAOYSA-N

Iso-THIP, or isoTHIP, is a selective and potent GABAA-ρ receptor (GABAC receptor) antagonist related to gaboxadol (THIP). It is 4-fold more potent than gaboxadol as a GABAA-ρ receptor antagonist. In addition to its GABAA-ρ receptor antagonism, iso-THIP shows much lower but still detectable affinity for the GABAA receptor, where it appears to be an antagonist similarly. The drug was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1979.

See also

References

  1. ↑ Frølund B, Ebert B, Kristiansen U, Liljefors T, Krogsgaard-Larsen P (August 2002). "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry. 2 (8): 817–832. doi:10.2174/1568026023393525. PMID 12171573.
  2. 1 2 3 Johnston GA, Chebib M, Hanrahan JR, Mewett KN (August 2003). "GABA(C) receptors as drug targets". Current Drug Targets. CNS and Neurological Disorders. 2 (4): 260–268. doi:10.2174/1568007033482805. PMID 12871036.
  3. 1 2 3 Krehan D, Frølund B, Ebert B, Nielsen B, Krogsgaard-Larsen P, Johnston GA, et al. (November 2003). "Aza-THIP and related analogues of THIP as GABA C antagonists". Bioorganic & Medicinal Chemistry. 11 (23): 4891–4896. doi:10.1016/j.bmc.2003.09.016. PMID 14604650.
  4. 1 2 Krogsgaard-Larsen P, Mikkelsen H, Jacobsen P, Falch E, Curtis DR, Peet MJ, et al. (June 1983). "4,5,6,7-Tetrahydroisothiazolo[5,4-c]pyridin-3-ol and related analogues of THIP. Synthesis and biological activity". Journal of Medicinal Chemistry. 26 (6): 895–900. doi:10.1021/jm00360a020. PMID 6304315.
  5. ↑ Arnt J, Krogsgaard-Larsen P (November 1979). "GABA agonists and potential antagonists related to muscimol". Brain Research. 177 (2): 395–400. doi:10.1016/0006-8993(79)90793-5. PMID 227538.