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Details

Stereochemistry ACHIRAL
Molecular Formula C4H7O3.Li
Molecular Weight 110.038
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LITHIUM OXYBATE

SMILES

[Li+].OCCCC([O-])=O

InChI

InChIKey=HQXIDRLGWYBFQL-UHFFFAOYSA-M
InChI=1S/C4H8O3.Li/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Li
Molecular Weight 6.941
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H7O3
Molecular Weight 103.0966
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Sodium oxybate is the sodium salt of gamma-hydroxybutyrate (GHB), an endogenous metabolite of gamma-aminobutyric acid (GABA) a major inhibitory neurotransmitter. Evidence suggests a role for GHB as a neuromodulator/neurotransmitter. Under endogenous conditions and concentrations, and depending on the cell group affected, GHB may increase or decrease neuronal activity by inhibiting the release of neurotransmitters that are co-localised with GHB. After exogenous administration, most of the observed behavioural effects appear to be mediated via the activity of GHB at GABA(B) receptors, as long as the concentration is sufficient to elicit binding, which does not happen at endogenous concentrations. Xyrem (sodium oxybate) oral solution is indicated for the treatment of cataplexy in narcolepsy and excessive daytime sleepiness (EDS) in narcolepsy.

Originator

Sources: Laborit H. (1964) Sodium 4-hydroxybutyrate. J Neuropharmacol 32: 433–452
Curator's Comment: Sodium oxybate (sodium salt of gamma-hydroxybutyrate (GHB) was first described as a possible precursor of GABA that could cross the blood-brain barrier [Laborit, 1964]. Further elucidation proved it an endogenous metabolite of GABA [Roth and Giarman, 1969] with a turnover of 0.16% of GABA being converted to GHB [Maitre, 1997] reference retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3382678/

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
100.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XYREM

Approved Use

XYREM® (sodium oxybate) oral solution is a central nervous system depressant indicated for the treatment of: • Cataplexy in narcolepsy • Excessive daytime sleepiness (EDS) in narcolepsy

Launch Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
54 μg/mL
25 mg/kg 2 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
23 μg/mL
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
20 μg/mL
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
23 μg/mL
12.5 mg/kg single, oral
dose: 12.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3122 μg × min/mL
25 mg/kg 2 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
1271 μg × min/mL
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1565 μg × min/mL
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
905 μg × min/mL
12.5 mg/kg single, oral
dose: 12.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
27 min
25 mg/kg 2 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
22 min
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
23 min
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
20 min
12.5 mg/kg single, oral
dose: 12.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
99%
12.5 mg/kg single, oral
dose: 12.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
4-HYDROXYBUTANOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Thyrotropin-releasing hormone-induced GH release after cocaine withdrawal in cocaine addicts.
1999 Dec
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.
2001
[The new drugs: ecstasy, GHB. Update for practitioners].
2001 Dec
Gamma-hydroxybutyrate withdrawal syndrome.
2001 Feb
Different control of GH secretion by gamma-amino- and gamma-hydroxy-butyric acid in 4-year abstinent alcoholics.
2001 Feb 1
A model of atypical absence seizures: EEG, pharmacology, and developmental characterization.
2001 Feb 13
Adverse events, including death, associated with the use of 1,4-butanediol.
2001 Jan 11
Baclofen antagonises intravenous self-administration of gamma-hydroxybutyric acid in mice.
2001 Jul 20
[Effect of lithium hydroxybutyrate on the circadian dynamics of the urinary excretion of Li(+), Na(+), K(+), and Ca(2+) in rats depending on the circadian phase of the drug administration].
2001 Jul-Aug
Improved procedure for the analysis of gamma-hydroxybutyrate and ethylene glycol in whole blood.
2001 Jul-Aug
It's a rave new world: rave culture and illicit drug use in the young.
2001 Jun
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate.
2001 Jun 12
Blood, brain, and hair GHB concentrations following fatal ingestion.
2001 May
Determination of gamma-hydroxybutyrate in water and human urine by solid phase microextraction-gas chromatography/quadrupole ion trap spectrometry.
2001 May
Selective breeding of two rat lines differing in sensitivity to GHB and baclofen.
2001 May 25
Inheritance pattern of RAPD markers in Melipona quadrifasciata (Hymenoptera: Apidae, Meliponinae).
2001 May-Jun
1H NMR spectroscopic investigation of serum and urine in a case of acute tetrahydrofuran poisoning.
2001 May-Jun
The chemical interconversion of GHB and GBL: forensic issues and implications.
2001 Nov
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.
2001 Nov
Management of gamma-hydroxybutyrate withdrawal.
2001 Nov
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors.
2001 Nov 2
[Autotrophic synthesis of polyalkanoates by Alcaligenes eutrophus in presence of carbon monoxide].
2001 Nov-Dec
A contemporaneous finding of fenproporex in a polydrug suicide.
2001 Oct
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.
2001 Oct 15
[Well-documented information on GHB].
2001 Oct 3
gamma-Hydroxybutyrate modulation of glutamate levels in the hippocampus: an in vivo and in vitro study.
2001 Sep
Patents

Sample Use Guides

Initiate dose at 4.5 grams (g) per night administered orally in two equal, divided doses: 2.25 g at bedtime and 2.25 g taken 2.5 to 4 hours later. Titrate to effect in increments of 1.5 g per night at weekly intervals (0.75 g at bedtime and 0.75 g taken 2.5 to 4 hours later). Recommended dose range: 6 g to 9 g per night orally.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: gamma-hydroxybutyrate (GHB) activates both pre- and postsynaptic GABA(B)-receptors in neocortical neurons participating in fast synaptic transmission, leading to a powerful depression of neocortical network activity.
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:31:59 GMT 2023
Edited
by admin
on Sat Dec 16 08:31:59 GMT 2023
Record UNII
R9BHS7060X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LITHIUM OXYBATE
Common Name English
BUTANOIC ACID, 4-HYDROXY-, LITHIUM SALT (1:1)
Systematic Name English
LITHIUM .GAMMA.-HYDROXYBUTYRATE
Systematic Name English
OXYBATE LITHIUM
WHO-DD  
Common Name English
Oxybate lithium [WHO-DD]
Common Name English
BUTANOIC ACID, 4-HYDROXY-, MONOLITHIUM SALT
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID20979300
Created by admin on Sat Dec 16 08:32:00 GMT 2023 , Edited by admin on Sat Dec 16 08:32:00 GMT 2023
PRIMARY
SMS_ID
300000017596
Created by admin on Sat Dec 16 08:32:00 GMT 2023 , Edited by admin on Sat Dec 16 08:32:00 GMT 2023
PRIMARY
CAS
63255-29-8
Created by admin on Sat Dec 16 08:32:00 GMT 2023 , Edited by admin on Sat Dec 16 08:32:00 GMT 2023
PRIMARY
PUBCHEM
23666120
Created by admin on Sat Dec 16 08:32:00 GMT 2023 , Edited by admin on Sat Dec 16 08:32:00 GMT 2023
PRIMARY
FDA UNII
R9BHS7060X
Created by admin on Sat Dec 16 08:32:00 GMT 2023 , Edited by admin on Sat Dec 16 08:32:00 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY