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Iso-THIP

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Pharmaceutical compound

Iso-THIP
Clinical data

Other names	IsoTHIP; Isogaboxadol
Drug class	GABA_A-ρ receptor antagonist;GABA_A receptor antagonist
ATC code	None
Identifiers
IUPAC name 4,5,6,7-tetrahydro-1H-[1,2]oxazolo[3,4-c]pyridin-3-one
CAS Number	71233-27-7
PubChemCID	130546
ChemSpider	115482
CompTox Dashboard(EPA)	DTXSID20991542
Chemical and physical data
Formula	C₆H₈N₂O₂
Molar mass	140.142 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CNCC2=C1C(=O)ON2
InChI 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, orisoTHIP, is aselective andpotent GABA_A-ρ receptor (GABA_C receptor)antagonist related togaboxadol (THIP).^[1]^[2]^[3] It is 4-fold more potent than gaboxadol as a GABA_A-ρ receptor antagonist.^[2]^[3] In addition to its GABA_A-ρ receptor antagonism, iso-THIP shows much lower but still detectableaffinity for the GABA_A receptor, where it appears to be an antagonist similarly.^[2]^[3]^[4] The drug was first described in thescientific literature byPovl Krogsgaard-Larsen and colleagues by 1979.^[4]^[5]

^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.
^^a ^b ^cJohnston 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.
^^a ^b ^cKrehan 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.
^^a ^bKrogsgaard-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.
^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.