γ-hydroxybutyrate   Click here for help

GtoPdb Ligand ID: 4711

Abbreviated name: GHB
Synonyms: γ-hydroxybutyric acid | Alcover® | WY-3478 | Xyrem®
Approved drug
γ-hydroxybutyrate is an approved drug (FDA (2002), EMA (2005))
Compound class: Metabolite
Comment: γ-hydroxybutyrate (GHB) is a metabolite of GABA.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 57.53
Molecular weight 104.05
XLogP -0.6
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCCCC(=O)O
Isomeric SMILES OCCCC(=O)O
InChI InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
InChI Key SJZRECIVHVDYJC-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used clinically to reduce excessive daytime sleepiness and cataplexy in patients with narcolepsy. Some countries approve use of sodium oxybate for the management of alcohol dependence.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
γ-hydroxybutyric acid (GHB) and related compounds primarily act on GABAB receptors to activate potassium channels. This causes neuronal hyperpolarisation, blocks sodium channel opening and prevents firing of action potentials and VGCC (voltage-gated calcium channel) opening. The cumulative effect is a reduction in neurotransmitter release which has an inhibitory effect in the CNS. GHB may also act via SLC52A2 (aka GHB receptor) [2-3].
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