{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = Aza-THIP.svg | image_class = skin-invert-image | width = 175px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = GABA<sub>A</sub>-ρ antagonist | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number = 654666-65-6 | CAS_supplemental = | PubChem = 55285412 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 27267416 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = Azagaboxadol
<!-- Chemical data --> | IUPAC_name = 1,2,4,5,6,7-hexahydropyrazolo[3,4-c]pyridin-3-one | C=6 | H=9 | N=3 | O=1 | SMILES = C1CNCC2=C1C(=O)NN2 | StdInChI = 1S/C6H9N3O/c10-6-4-1-2-7-3-5(4)8-9-6/h7H,1-3H2,(H2,8,9,10) | StdInChIKey = UPMMUUFLHUEUKP-UHFFFAOYSA-N }}
'''Aza-THIP''' is a selective and moderately potent GABA<sub>A</sub>-ρ (GABA<sub>C</sub> receptor) antagonist related to gaboxadol (THIP).<ref name="KrogsgaardLarsen_2006">{{cite book | vauthors = Krogsgaard-Larsen P, Frølund B, Liljefors T | title = GABA(A) agonists and partial agonists: THIP (Gaboxadol) as a non-opioid analgesic and a novel type of hypnotic | chapter = GABAA Agonists and Partial Agonists: THIP (Gaboxadol) as a Non-Opioid Analgesic and a Novel Type of Hypnotic1 | series = Advances in Pharmacology | volume = 54 | pages = 53–71 | date = 2006 | pmid = 17175810 | doi = 10.1016/s1054-3589(06)54003-7 | isbn = 978-0-12-032957-1 }}</ref><ref name="Johnston_2003">{{cite journal | vauthors = Johnston GA, Chebib M, Hanrahan JR, Mewett KN | title = GABA(C) receptors as drug targets | journal = Current Drug Targets. CNS and Neurological Disorders | volume = 2 | issue = 4 | pages = 260–268 | date = August 2003 | pmid = 12871036 | doi = 10.2174/1568007033482805 }}</ref><ref name="Johnston_2010">{{cite journal | vauthors = Johnston GA, Chebib M, Hanrahan JR, Mewett KN | title = Neurochemicals for the investigation of GABA(C) receptors | journal = Neurochemical Research | volume = 35 | issue = 12 | pages = 1970–1977 | date = December 2010 | pmid = 20963487 | doi = 10.1007/s11064-010-0271-7 }}</ref><ref name="Krehan_2003">{{cite journal | vauthors = Krehan D, Frølund B, Ebert B, Nielsen B, Krogsgaard-Larsen P, Johnston GA, Chebib M | title = Aza-THIP and related analogues of THIP as GABA C antagonists | journal = Bioorganic & Medicinal Chemistry | volume = 11 | issue = 23 | pages = 4891–4896 | date = November 2003 | pmid = 14604650 | doi = 10.1016/j.bmc.2003.09.016 }}</ref> Unlike gaboxadol, it is virtually inactive at the GABA<sub>A</sub> receptor.<ref name="KrogsgaardLarsen_2006" /><ref name="Johnston_2003" /><ref name="Krehan_2003" /><ref name="Frlund_2002">{{cite journal | vauthors = Frølund B, Ebert B, Kristiansen U, Liljefors T, Krogsgaard-Larsen P | title = GABA(A) receptor ligands and their therapeutic potentials | journal = Current Topics in Medicinal Chemistry | volume = 2 | issue = 8 | pages = 817–832 | date = August 2002 | pmid = 12171573 | doi = 10.2174/1568026023393525 }}</ref> The drug was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1979.<ref name="KrogsgaardLarsen_1981">{{cite journal | vauthors = Krogsgaard-Larsen P, Falch E | title = GABA agonists. Development and interactions with the GABA receptor complex | journal = Molecular and Cellular Biochemistry | volume = 38 Spec No | issue = Pt 1 | pages = 129–146 | date = August 1981 | pmid = 6270544 | doi = 10.1007/BF00235692 }}</ref><ref name="citefb42a462">{{cite journal | vauthors = Krogsgaard-Larsen P, Roldskov-Christiansen T | title = GABA agonists. Synthesis and structure-activity studies on analogs of isoguvacine and THIP. | date = 1979 | journal = Chimica Therapeutica (European Journal of Medicinal Chemistry) | volume = 14 | pages = 157–164 }}</ref>
== See also == * Thio-THIP * Iso-THIP * THAZ
== References == {{Reflist}}
{{GABA receptor modulators}}
Category:GABA analogues Category:GABAA-rho receptor antagonists Category:Ketones Category:Pyrazolopyridines
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