Gaboxadol

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
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.

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Contraindications & Blackbox Warnings
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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
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Gaboxadol is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Gaboxadol.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Gaboxadol.
AgomelatineThe risk or severity of CNS depression can be increased when Gaboxadol is combined with Agomelatine.
AlfentanilThe 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
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
PhaseStatusPurposeConditionsCount
3CompletedTreatmentInsomnia4
3CompletedTreatmentPrimary Disease or Condition Being Studied: Angelman Syndrome (AS)1
3CompletedTreatmentPrimary Insomnia6
3TerminatedTreatmentAngelman's syndrome1
3TerminatedTreatmentPrimary Insomnia2

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
PropertyValueSource
Water Solubility16.6 mg/mLALOGPS
logP-1.3ALOGPS
logP-2Chemaxon
logS-0.93ALOGPS
pKa (Strongest Acidic)5.12Chemaxon
pKa (Strongest Basic)8.85Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area50.36 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity35.5 m3·mol-1Chemaxon
Polarizability13.31 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-f325081bb1d44c00f26e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-a6fff1f00080536fd767
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000y-8900000000-49aae2e5671d9e221673
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-020r-9600000000-6abd77a7361fa11fb8d0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-9100000000-596158593cb46a479a48
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004m-9000000000-8ddd945d1a7950d0d883
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-123.8923101
predicted
DarkChem Lite v0.1.0
[M-H]-124.78358
predicted
DeepCCS 1.0 (2019)
[M+H]+124.7310101
predicted
DarkChem Lite v0.1.0
[M+H]+127.0962
predicted
DeepCCS 1.0 (2019)
[M+Na]+124.2092101
predicted
DarkChem Lite v0.1.0
[M+Na]+135.65137
predicted
DeepCCS 1.0 (2019)

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
  1. 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