Iso-THIP

Iso-THIP
Clinical data
Other names	IsoTHIP; Isogaboxadol
Drug class	GABAA-ρ receptor antagonist; GABAA 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;
PubChem CID	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, or isoTHIP, is a selective and potent GABA_A-ρ receptor (GABA_C receptor) antagonist related to gaboxadol (THIP).¹²³ It is 4-fold more potent than gaboxadol as a GABA_A-ρ receptor antagonist.²³ In addition to its GABA_A-ρ receptor antagonism, iso-THIP shows much lower but still detectable affinity for the GABA_A receptor, where it appears to be an antagonist similarly.²³⁴ The drug was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1979.⁴⁵

References

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.
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.
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.
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.
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.

[Frlund_2002-1] 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.

[Johnston_2003-2] 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.

[Krehan_2003-3] 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.

[KrogsgaardLarsen_1983-4] 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.

[Arnt_1979-5] 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.

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See also

References