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
- Not Available
- 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. Alimemazine The risk or severity of CNS depression can be increased when Alimemazine is combined with Gaboxadol. Almotriptan The risk or severity of CNS depression can be increased when Almotriptan is combined with Gaboxadol. Alosetron The risk or severity of CNS depression can be increased when Alosetron is combined with Gaboxadol. Alprazolam The risk or severity of CNS depression can be increased when Alprazolam is combined with Gaboxadol. Alverine The risk or severity of CNS depression can be increased when Alverine is combined with Gaboxadol. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
Phase Status Purpose Conditions Count 3 Completed Treatment Insomnia 4 3 Completed Treatment Primary Disease or Condition Being Studied: Angelman Syndrome (AS) 1 3 Completed Treatment Primary Insomnia 6 3 Terminated Treatment Angelman's syndrome 1 3 Terminated Treatment Primary Insomnia 2 3 Withdrawn Treatment Insomnia 1 2 Completed Treatment Angelman's syndrome 1 2 Completed Treatment Fragile X Syndrome 1 2 Completed Treatment Major Depressive Disorder (MDD) 1 2 Completed Treatment Primary Insomnia 1
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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- L-proline transmembrane transporter activity
- Specific Function
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recog...
- 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 November 03, 2022 16:14