gaboxadol (BioDeep_00000858863)

Main id: BioDeep_00000009512

 


代谢物信息卡片


4,5,6,7-tetrahydroisoxazolo(5,4-c)Pyridin-3-ol

化学式: C6H8N2O2 (140.0585748)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CNCC2=C1C(=O)NO2
InChI: InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)

描述信息

D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018755 - GABA Agonists
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000927 - Anticonvulsants
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent
D002491 - Central Nervous System Agents > D000700 - Analgesics
Same as: D04282
THIP (Gaboxadol) is a selective extrasynaptic GABAA receptors (eGABARs) agonist (with blood-brain barrier permeability), shows an EC50 value of 13 μM for δ-GABAAR. THIP induces strong tense GABAA-mediated currents in layer 2/3 neurons, but shows on effect on miniature IPSCs. THIP can be used in studies of sleep disorders[1][2][3].

同义名列表

3 个代谢物同义名

4,5,6,7-tetrahydroisoxazolo(5,4-c)Pyridin-3-ol; gaboxadol; THIP



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

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COVID-19 Disease Map(0)

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0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Bence Szilágyi, Péter Kovács, György G Ferenczy, Anita Rácz, Krisztina Németh, Júlia Visy, Pál Szabó, Janez Ilas, György T Balogh, Katalin Monostory, István Vincze, Tamás Tábi, Éva Szökő, György M Keserű. Discovery of isatin and 1H-indazol-3-ol derivatives as d-amino acid oxidase (DAAO) inhibitors. Bioorganic & medicinal chemistry. 2018 05; 26(8):1579-1587. doi: 10.1016/j.bmc.2018.02.004. [PMID: 29472125]
  • Filippos Kesisoglou, Anand Balakrishnan, Kimberly Manser. Utility of PBPK Absorption Modeling to Guide Modified Release Formulation Development of Gaboxadol, a Highly Soluble Compound With Region-Dependent Absorption. Journal of pharmaceutical sciences. 2016 Feb; 105(2):722-728. doi: 10.1002/jps.24674. [PMID: 26457884]
  • Rune Nørgaard Rasmussen, Candela Lagunas, Jakob Plum, René Holm, Carsten Uhd Nielsen. Interaction of GABA-mimetics with the taurine transporter (TauT, Slc6a6) in hyperosmotic treated Caco-2, LLC-PK1 and rat renal SKPT cells. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2016 Jan; 82(?):138-46. doi: 10.1016/j.ejps.2015.11.020. [PMID: 26631583]
  • Marco I González, Heidi L Grabenstatter, Christian A Cea-Del Rio, Yasmin Cruz Del Angel, Jessica Carlsen, Rick P Laoprasert, Andrew M White, Molly M Huntsman, Amy Brooks-Kayal. Seizure-related regulation of GABAA receptors in spontaneously epileptic rats. Neurobiology of disease. 2015 May; 77(?):246-56. doi: 10.1016/j.nbd.2015.03.001. [PMID: 25769812]
  • C U Nielsen, S Frølund, S Abdulhadi, H Sari, L Langthaler, M K Nøhr, M A Kall, B Brodin, R Holm. Sertraline inhibits the transport of PAT1 substrates in vivo and in vitro. British journal of pharmacology. 2013 Nov; 170(5):1041-52. doi: 10.1111/bph.12341. [PMID: 23962042]
  • Anna M Wójtowicz, Anton Dvorzhak, Marcus Semtner, Rosemarie Grantyn. Reduced tonic inhibition in striatal output neurons from Huntington mice due to loss of astrocytic GABA release through GAT-3. Frontiers in neural circuits. 2013; 7(?):188. doi: 10.3389/fncir.2013.00188. [PMID: 24324407]
  • Kiyoshi Egawa, Kyoko Kitagawa, Koichi Inoue, Masakazu Takayama, Chitoshi Takayama, Shinji Saitoh, Tatsuya Kishino, Masatoshi Kitagawa, Atsuo Fukuda. Decreased tonic inhibition in cerebellar granule cells causes motor dysfunction in a mouse model of Angelman syndrome. Science translational medicine. 2012 Dec; 4(163):163ra157. doi: 10.1126/scitranslmed.3004655. [PMID: 23220633]
  • Nicole Sabaliauskas, Hui Shen, Gregg E Homanics, Sheryl S Smith, Chiye Aoki. Knockout of the γ-aminobutyric acid receptor subunit α4 reduces functional δ-containing extrasynaptic receptors in hippocampal pyramidal cells at the onset of puberty. Brain research. 2012 Apr; 1450(?):11-23. doi: 10.1016/j.brainres.2012.02.035. [PMID: 22418059]
  • Rigobert Ayissi Mbomo, Sasha Gartside, Elizabeth Ngo Bum, Njifutie Njikam, Ed Okello, Richard McQuade. Effect of Mimosa pudica (Linn.) extract on anxiety behaviour and GABAergic regulation of 5-HT neuronal activity in the mouse. Journal of psychopharmacology (Oxford, England). 2012 Apr; 26(4):575-83. doi: 10.1177/0269881111398686. [PMID: 21427203]
  • Agnès Petit-Paitel, Baptiste Ménard, Alice Guyon, Vincent Béringue, Jean-Louis Nahon, Nicole Zsürger, Joëlle Chabry. Prion protein is a key determinant of alcohol sensitivity through the modulation of N-methyl-D-aspartate receptor (NMDAR) activity. PloS one. 2012; 7(4):e34691. doi: 10.1371/journal.pone.0034691. [PMID: 22536327]
  • David T Thwaites, Catriona M H Anderson. The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport. British journal of pharmacology. 2011 Dec; 164(7):1802-16. doi: 10.1111/j.1476-5381.2011.01438.x. [PMID: 21501141]
  • Karsten K Madsen, Bjarke Ebert, Rasmus P Clausen, Povl Krogsgaard-Larsen, Arne Schousboe, H Steve White. Selective GABA transporter inhibitors tiagabine and EF1502 exhibit mechanistic differences in their ability to modulate the ataxia and anticonvulsant action of the extrasynaptic GABA(A) receptor agonist gaboxadol. The Journal of pharmacology and experimental therapeutics. 2011 Jul; 338(1):214-9. doi: 10.1124/jpet.111.179671. [PMID: 21450931]
  • Martin Mortensen, Bjarke Ebert, Keith Wafford, Trevor G Smart. Distinct activities of GABA agonists at synaptic- and extrasynaptic-type GABAA receptors. The Journal of physiology. 2010 Apr; 588(Pt 8):1251-68. doi: 10.1113/jphysiol.2009.182444. [PMID: 20176630]
  • M Larsen, R Holm, K G Jensen, B Brodin, C U Nielsen. Intestinal gaboxadol absorption via PAT1 (SLC36A1): modified absorption in vivo following co-administration of L-tryptophan. British journal of pharmacology. 2009 Aug; 157(8):1380-9. doi: 10.1111/j.1476-5381.2009.00253.x. [PMID: 19594759]
  • Xiao-Yan Chu, Yuexia Liang, Xiaoxin Cai, Karla Cuevas-Licea, Ronda K Rippley, Kelem Kassahun, Magang Shou, Matthew P Braun, George A Doss, M Reza Anari, Raymond Evers. Metabolism and renal elimination of gaboxadol in humans: role of UDP-glucuronosyltransferases and transporters. Pharmaceutical research. 2009 Feb; 26(2):459-68. doi: 10.1007/s11095-008-9799-5. [PMID: 19082692]
  • L M McDonald, W F Sheppard, S M Staveley, B Sohal, F D Tattersall, P H Hutson. Discriminative stimulus effects of tiagabine and related GABAergic drugs in rats. Psychopharmacology. 2008 May; 197(4):591-600. doi: 10.1007/s00213-008-1077-z. [PMID: 18264695]
  • Morten A Kall, Irong Fu, Tina Dige, Patrick Vallano, Eric Woolf, Martin Jørgensen. Development and validation of a selective and sensitive bioanalytical procedure for the quantitative determination of gaboxadol in human plasma employing mixed mode solid phase extraction and hydrophilic interaction liquid chromatography with tandem mass spectroscopic detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Oct; 858(1-2):168-76. doi: 10.1016/j.jchromb.2007.08.029. [PMID: 17851145]
  • Thomas Cremers, Bjarke Ebert. Plasma and CNS concentrations of Gaboxadol in rats following subcutaneous administration. European journal of pharmacology. 2007 May; 562(1-2):47-52. doi: 10.1016/j.ejphar.2007.01.017. [PMID: 17362924]
  • Pavel I Ortinski, Jill R Turner, Andrea Barberis, Gholam Motamedi, Robert P Yasuda, Barry B Wolfe, Kenneth J Kellar, Stefano Vicini. Deletion of the GABA(A) receptor alpha1 subunit increases tonic GABA(A) receptor current: a role for GABA uptake transporters. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2006 Sep; 26(36):9323-31. doi: 10.1523/jneurosci.2610-06.2006. [PMID: 16957088]
  • Marco L Lolli, Suzanne L Hansen, Barbara Rolando, Birgitte Nielsen, Petrine Wellendorph, Karsten Madsen, Orla Miller Larsen, Uffe Kristiansen, Roberta Fruttero, Alberto Gasco, Tommy N Johansen. Hydroxy-1,2,5-oxadiazolyl moiety as bioisoster of the carboxy function. Synthesis, ionization constants, and pharmacological characterization of gamma-aminobutyric acid (GABA) related compounds. Journal of medicinal chemistry. 2006 Jul; 49(14):4442-6. doi: 10.1021/jm051288b. [PMID: 16821803]
  • Martin Mortensen, Uffe Kristiansen, Bjarke Ebert, Bente Frølund, Povl Krogsgaard-Larsen, Trevor G Smart. Activation of single heteromeric GABA(A) receptor ion channels by full and partial agonists. The Journal of physiology. 2004 Jun; 557(Pt 2):389-413. doi: 10.1113/jphysiol.2003.054734. [PMID: 14990676]
  • R Gomez, N Asnis, S L Tannhauser, H M Barros. GABA agonists differentially modify blood glucose levels of diabetic rats. Japanese journal of pharmacology. 1999 Aug; 80(4):327-31. doi: 10.1254/jjp.80.327. [PMID: 10496333]
  • S L Waters, G W Miller, M D Aleo, R G Schnellmann. Neurosteroid inhibition of cell death. The American journal of physiology. 1997 12; 273(6):F869-76. doi: 10.1152/ajprenal.1997.273.6.f869. [PMID: 9435674]
  • T Kusama, C E Spivak, P Whiting, V L Dawson, J C Schaeffer, G R Uhl. Pharmacology of GABA rho 1 and GABA alpha/beta receptors expressed in Xenopus oocytes and COS cells. British journal of pharmacology. 1993 May; 109(1):200-6. doi: 10.1111/j.1476-5381.1993.tb13554.x. [PMID: 8388298]
  • G H Hansen, B Belhage, A Schousboe. First direct electron microscopic visualization of a tight spatial coupling between GABAA-receptors and voltage-sensitive calcium channels. Neuroscience letters. 1992 Mar; 137(1):14-8. doi: 10.1016/0304-3940(92)90287-h. [PMID: 1320751]
  • S Rajaram, S Ramaswamy, J S Bapna. Role of calcium in the analgesic action of tetrahydroisoxazolepyridinol and muscimol. The Journal of pharmacy and pharmacology. 1991 Jun; 43(6):440-1. doi: 10.1111/j.2042-7158.1991.tb03506.x. [PMID: 1681060]
  • G H Hansen, B Belhage, A Schousboe. Effect of a GABA agonist on the expression and distribution of GABAA receptors in the plasma membrane of cultured cerebellar granule cells: an immunocytochemical study. Neuroscience letters. 1991 Apr; 124(2):162-5. doi: 10.1016/0304-3940(91)90084-7. [PMID: 1648687]
  • B Belhage, G H Hansen, E Meier, A Schousboe. Effects of inhibitors of protein synthesis and intracellular transport on the gamma-aminobutyric acid agonist-induced functional differentiation of cultured cerebellar granule cells. Journal of neurochemistry. 1990 Oct; 55(4):1107-13. doi: 10.1111/j.1471-4159.1990.tb03112.x. [PMID: 2168931]
  • A Michler. Involvement of GABA receptors in the regulation of neurite growth in cultured embryonic chick tectum. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience. 1990; 8(4):463-72. doi: 10.1016/0736-5748(90)90078-g. [PMID: 2174636]
  • J V Andersen, L Dalgaard, S H Hansen. Enzymic synthesis of two glucuronides of the hydroxyisoxazole GABA-agonist, THIP, and the in vivo glucuronidation of THIP in rat. Xenobiotica; the fate of foreign compounds in biological systems. 1989 Dec; 19(12):1399-406. doi: 10.3109/00498258909043191. [PMID: 2618090]
  • M Fujimoto, Y Kataoka, A Guidotti, I Hanbauer. Effect of gamma-aminobutyric acidA receptor agonists and antagonists on the release of enkephalin-containing peptides from dog adrenal gland. The Journal of pharmacology and experimental therapeutics. 1987 Oct; 243(1):195-9. doi: NULL. [PMID: 2822897]
  • W Löscher. Development of tolerance to the anticonvulsant effect of GABAmimetic drugs in genetically epilepsy-prone gerbils. Pharmacology, biochemistry, and behavior. 1986 Apr; 24(4):1007-13. doi: 10.1016/0091-3057(86)90449-1. [PMID: 3086900]
  • A G Chapman. Valproate and myoclonus. Advances in neurology. 1986; 43(?):661-74. doi: NULL. [PMID: 3080855]
  • G H Fromm, C F Terrence, A S Chattha. Comparison of progabide with other antiepileptic and GABAergic drugs. Epilepsia. 1985 Nov; 26(6):672-81. doi: 10.1111/j.1528-1157.1985.tb05710.x. [PMID: 3000759]
  • J N Crawley, P T Ninan, D Pickar, G P Chrousos, M Linnoila, P Skolnick, S M Paul. Neuropharmacological antagonism of the beta-carboline-induced 'anxiety' response in rhesus monkeys. The Journal of neuroscience : the official journal of the Society for Neuroscience. 1985 Feb; 5(2):477-85. doi: 10.1523/jneurosci.05-02-00477.1985. [PMID: 2983041]
  • M Kjaer, H Nielsen. The analgesic effect of the GABA-agonist THIP in patients with chronic pain of malignant origin. A phase-1-2 study. British journal of clinical pharmacology. 1983 Nov; 16(5):477-85. doi: 10.1111/j.1365-2125.1983.tb02203.x. [PMID: 6639833]
  • S M Madsen, T Lindeburg, S Følsgård, E Jacobsen, H Sillesen. Pharmacokinetics of the gamma-aminobutyric acid agonist THIP (Gaboxadol) following intramuscular administration to man, with observations in dog. Acta pharmacologica et toxicologica. 1983 Nov; 53(5):353-7. doi: 10.1111/j.1600-0773.1983.tb03434.x. [PMID: 6659963]
  • S M Madsen. Quantitative determination of the gamma-aminobutyric acid agonist, 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol, in serum by high-performance liquid chromatography. Journal of chromatography. 1983 May; 274(?):209-18. doi: 10.1016/s0378-4347(00)84424-2. [PMID: 6874822]
  • T Lindeburg, S Følsgård, H Sillesen, E Jacobsen, H Kehlet. Analgesic, respiratory and endocrine responses in normal man to THIP, a GABA-agonist. Acta anaesthesiologica Scandinavica. 1983 Feb; 27(1):10-2. doi: 10.1111/j.1399-6576.1983.tb01896.x. [PMID: 6837230]
  • B Schultz, T Aaes-Jørgensen, K P Bøgesø, A Jørgensen. Preliminary studies on the absorption, distribution, metabolism, and excretion of THIP in animal and man using 14C-labelled compound. Acta pharmacologica et toxicologica. 1981 Aug; 49(2):116-24. doi: 10.1111/j.1600-0773.1981.tb00879.x. [PMID: 7336969]