General
Preferred name
gamma-Hydroxybutyric acid
Synonyms
SODIUM OXYBATE ()
GHB ()
OXYBATE ()
Xyrem ()
Gamma hydroxybutyric acid ()
CALCIUM OXYBATE ()
MAGNESIUM OXYBATE ()
POTASSIUM OXYBATE ()
Catabate ()
WY-3478 ()
NSC-84223 ()
Oxybate sodium ()
Sodium oxybutyrate ()
.gamma.-hydroxybutyrate sodium salt ()
Lumryz ()
Sodium oxybat ()
γ-hydroxybutyrate ()
Gamma hydroxybutyrate ()
Gamma-hydroxybutyrate ()
.gamma.-hydroxybutyrate ()
Oxybate calcium ()
Oxybate magnesium ()
Oxybate potassium ()
GHB (sodium salt) ()
GHB (sodium salt) (exempt preparation) ()
GHB-d6 (sodium salt) ()
P&D ID
PD051728
CAS
502-85-2
82316-97-0
362049-53-4
1320-61-2
52352-27-9
591-81-1
Tags
natural product
drug
available
Drug Status
illicit
investigational
approved
Drug indication
Anesthesia, Adjunct To
Narcolepsy
Max Phase
Phase 4
First approval
2020
2002
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION For the treatment of cataplexy and excessive daytime sleepiness (EDS) associated with narcolepsy.
ROE Animal studies indicate that metabolism is the major elimination pathway for sodium oxybate, producing carbon dioxide and water via the tricarboxylic acid (Krebs) cycle and secondarily by beta-oxidation. Succinic acid enters the Krebs cycle where it is metabolized to carbon dioxide and water. Fecal and renal excretion is negligible.; 5% renal elimination.
TOXICITY High doses of GHB may lead to nausea, dizziness, drowsiness, agitation, visual disturbances, depressed breathing, amnesia, unconsciousness, and death in some cases.
DESCRIPTION γ-hydroxybutyrate (GHB) is a metabolite of . (GtoPdb)
PHARMACODYNAMICS GHB predominantly works at two distinct binding sites in the central nervous system: it works as an agonist at the newly-characterized excitatory GHB receptor, while acting as a weak agonist at the inhibitory GABAB receptor. Since it is a naturally occurring substance, its physiological action is similar to that of some endogenous neurotransmitters in mammalian brain. GHB is probably synthesized from GABA in GABAergic neurons, and released when the neurons fire.
MOA GHB is present at much higher concentrations in the brain, where it activates GABA-B receptors to exert its sedative effects. With high affinity, GHB binds to excitatory GHB receptors that are densely expressed throughout the brain, including the cotex and hippocampus. There is some evidence in research that upon activation of GHB receptors in some brain areas, the excitatory neurotransmitter glutamate is released. GHB stimulates dopamin release at low concentrations by acting on the GHB receptor, and the release of dopamine occurs in a biphasic manner. At higher concentrations, GHB inhibits dopamine release by acting on the GABA-B receptors, which is followed by GHB receptor signaling and increased release of dopamine. This explains the paradoxical mix of sedative and stimulatory properties of GHB, as well as the so-called "rebound" effect, experienced by individuals using GHB as a sleeping agent, wherein they awake suddenly after several hours of GHB-induced deep sleep. It is proposed that overtime, the level of GHB in the brain decreases below the threshold for significant GABA-B receptor activation, leading to preferential activation of GHB receptor over GABA-B receptors and enhanced wakefulness.
Compound Sets
17
Cayman Chemical Bioactives
15661
9002506
21924
ChEMBL Approved Drugs
CHEMBL1200682
CHEMBL1342
CHEMBL4594395
CHEMBL4594394
CHEMBL4594393
ChEMBL Drugs
CHEMBL1200682
CHEMBL1342
CHEMBL4594395
CHEMBL4594394
CHEMBL4594393
Concise Guide to Pharmacology 2017/18
4711
Concise Guide to Pharmacology 2019/20
4711
Concise Guide to Pharmacology 2021/22
4711
Concise Guide to Pharmacology 2023/24
4711
DrugBank
DB09072
DB01440
DrugBank Approved Drugs
DB09072
DB01440
DrugMAP
DMGBKVD
DrugMAP Approved Drugs
DMGBKVD
Guide to Pharmacology
4711
Ki Database
GHB
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
30IW36W5B2
Other bioactive compounds
The Spectrum Collection
External IDs
99
Properties
(calculated by RDKit )
Molecular Weight
104.05
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
3
Ring Count
0
Aromatic Ring Count
0
cLogP
-0.16
TPSA
57.53
Fraction CSP3
0.75
Chiral centers
0.0
Largest ring
0.0
QED
0.52
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Therapeutic Indication
Antinarcolepsy
Therapeutic Class
CNS & PNS
Anesthetics
Source data