Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Gaboxadol
- DrugBank Accession Number
- DB06554
- Background
Gaboxadol also known as 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol (THIP) is an experimental sleep aid drug developed by Lundbeck and Merck, who reported increased deep sleep without the reinforcing effects of benzodiazepines. Development of Gaboxadol was stopped in March 2007 after concerns regarding safety and efficacy. It acts on the GABA system, but in a seemingly different way from benzodiazepines and other sedatives.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Gaboxadol (DB06554)
- Weight
- Average: 140.1399
Monoisotopic: 140.05857751 - Chemical Formula
- C6H8N2O2
- Synonyms
- 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol
- Gaboxadol
- THIP
- External IDs
- Lu 02-030
- MK-0928
- MK0928
Pharmacology
- Indication
Investigated for use/treatment in sleep disorders and insomnia.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AGamma-aminobutyric acid receptor subunit delta modulatorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Gaboxadol is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Gaboxadol. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Gaboxadol. Agomelatine The risk or severity of CNS depression can be increased when Gaboxadol is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Gaboxadol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- Isoxazoles / Heteroaromatic compounds / Oxacyclic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Isoxazole / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- oxazole (CHEBI:34373)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- K1M5RVL18S
- CAS number
- 64603-91-4
- InChI Key
- ZXRVKCBLGJOCEE-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)
- IUPAC Name
- 2H,3H,4H,5H,6H,7H-[1,2]oxazolo[5,4-c]pyridin-3-one
- SMILES
- O=C1NOC2=C1CCNC2
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0252570
- KEGG Drug
- D04282
- KEGG Compound
- C13693
- PubChem Compound
- 3448
- PubChem Substance
- 175427072
- ChemSpider
- 3330
- BindingDB
- 50224809
- ChEBI
- 34373
- ChEMBL
- CHEMBL312443
- ZINC
- ZINC000019795995
- PDBe Ligand
- EI7
- Wikipedia
- Gaboxadol
- PDB Entries
- 7qnc / 7qnd
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Insomnia 4 somestatus stop reason just information to hide 3 Completed Treatment Primary Disease or Condition Being Studied: Angelman Syndrome (AS) 1 somestatus stop reason just information to hide 3 Completed Treatment Primary Insomnia 6 somestatus stop reason just information to hide 3 Terminated Treatment Angelman's syndrome 1 somestatus stop reason just information to hide 3 Terminated Treatment Primary Insomnia 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 16.6 mg/mL ALOGPS logP -1.3 ALOGPS logP -2 Chemaxon logS -0.93 ALOGPS pKa (Strongest Acidic) 5.12 Chemaxon pKa (Strongest Basic) 8.85 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 50.36 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 35.5 m3·mol-1 Chemaxon Polarizability 13.31 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0900000000-f325081bb1d44c00f26e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0900000000-a6fff1f00080536fd767 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000y-8900000000-49aae2e5671d9e221673 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-020r-9600000000-6abd77a7361fa11fb8d0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001j-9100000000-596158593cb46a479a48 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004m-9000000000-8ddd945d1a7950d0d883 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 123.8923101 predictedDarkChem Lite v0.1.0 [M-H]- 124.78358 predictedDeepCCS 1.0 (2019) [M+H]+ 124.7310101 predictedDarkChem Lite v0.1.0 [M+H]+ 127.0962 predictedDeepCCS 1.0 (2019) [M+Na]+ 124.2092101 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.65137 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Delta subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:35355020). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:35355020). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:35355020). GABAARs containing delta/GABRD subunits are predominantly located in extrasynaptic or perisynaptic positions on hippocampus and cerebellar granule cells, and contribute to the tonic GABAergic inhibition (By similarity). GABAAR containing alpha-4-beta-3-delta subunits can simultaneously bind GABA and histamine where histamine binds at the interface of two neighboring beta subunits, which may be involved in the regulation of sleep and wakefulness (PubMed:35355020)
- Specific Function
- Chloride channel activity
- Gene Name
- GABRD
- Uniprot ID
- O14764
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit delta
- Molecular Weight
- 50707.835 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Electrogenic proton/amino acid symporter with selectivity for small apolar L-amino acids, their D-enantiomers and selected amino acid derivatives such as 4-aminobutanoate/GABA (PubMed:12527723, PubMed:12809675, PubMed:19549785). May be involved in the efflux from the lysosomal compartment of neutral amino acids resulting from proteolysis (By similarity). May play a role in specifying sites for exocytosis in neurons (By similarity)
- Specific Function
- Alanine transmembrane transporter activity
- Gene Name
- SLC36A1
- Uniprot ID
- Q7Z2H8
- Uniprot Name
- Proton-coupled amino acid transporter 1
- Molecular Weight
- 53075.045 Da
References
- Larsen M, Holm R, Jensen KG, Sveigaard C, Brodin B, Nielsen CU: 5-Hydroxy-L-tryptophan alters gaboxadol pharmacokinetics in rats: involvement of PAT1 and rOat1 in gaboxadol absorption and elimination. Eur J Pharm Sci. 2010 Jan 31;39(1-3):68-75. doi: 10.1016/j.ejps.2009.10.013. Epub 2009 Nov 10. [Article]
Drug created at March 19, 2008 16:36 / Updated at August 26, 2024 19:24