Gaboxadol

Synonyms :
4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol, THIP

Status : investigational

Description

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. In March, 2007, Merck and H. Lundbeck cancelled work on the drug, citing safety concerns and the failure of an efficacy trial. It acts on the GABA system, but possibly in a different way from benzodiazepines, nonbenzodiazepines and barbiturates – (Valium, Sodium Pentothal, Ambien etc.). Lundbeck states that gaboxadol also increases deep sleep (stage 4). It is, however, not reinforcing like benzodiazepines are. [Wikipedia]

Used

Investigated for use/treatment in sleep disorders and insomnia.

Chemical Classification

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.

Aralkylamines

Organic compounds

Organonitrogen compounds

Amines

Aralkylamines

Chemical Name

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

Calculated Property

kind Value Source
logP -1.3 ALOGPS
logS -0.93 ALOGPS
Water Solubility 1.66e+01 g/l ALOGPS
logP -2 ChemAxon
IUPAC Name 2H,3H,4H,5H,6H,7H-[1,2]oxazolo[5,4-c]pyridin-3-one ChemAxon
Traditional IUPAC Name gaboxadol ChemAxon
Molecular Weight 140.1399 ChemAxon
Monoisotopic Weight 140.05857751 ChemAxon
SMILES O=C1NOC2=C1CCNC2 ChemAxon
Molecular Formula C6H8N2O2 ChemAxon
InChI InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9) ChemAxon
InChIKey InChIKey=ZXRVKCBLGJOCEE-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 50.36 ChemAxon
Refractivity 35.5 ChemAxon
Polarizability 13.31 ChemAxon
Rotatable Bond Count 0 ChemAxon
H Bond Acceptor Count 3 ChemAxon
H Bond Donor Count 2 ChemAxon
pKa (strongest acidic) 5.12 ChemAxon
pKa (strongest basic) 8.85 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals