Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H7O3.K |
Molecular Weight | 142.1949 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].OCCCC([O-])=O
InChI
InChIKey=TXSIWDVUJVMMKM-UHFFFAOYSA-M
InChI=1S/C4H8O3.K/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1
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.
CNS Activity
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2111463 Sources: http://pp.jazzpharma.com/pi/xyrem.en.USPI.pdf |
100.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | XYREM Approved UseXYREM® (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 Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1389947 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3122 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1389947 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1389947 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
99% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669 |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 29, 35 |
no [IC50 >300 uM] | |||
Page: 29, 35 |
no [IC50 >300 uM] | |||
Page: 29, 35 |
no [IC50 >300 uM] | |||
Page: 29, 35 |
no [IC50 >300 uM] | |||
Page: 29, 35 |
no [IC50 >300 uM] | |||
Page: 29, 35 |
no [IC50 >300 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
Evidence for a G protein-coupled gamma-hydroxybutyric acid receptor. | 2000 Nov |
|
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR. | 2001 |
|
Properties, modifications and applications of biopolyesters. | 2001 |
|
The many faces of ecstasy. | 2001 Apr |
|
[The new drugs: ecstasy, GHB. Update for practitioners]. | 2001 Dec |
|
[Gamma hydroxy butyrate intoxication]. | 2001 Dec |
|
Binding characteristics of the gamma-hydroxybutyric acid receptor antagonist [(3)H](2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene) ethanoic acid in the rat brain. | 2001 Dec |
|
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product. | 2001 Feb |
|
Successful management of prolonged gamma-hydroxybutyrate and alcohol withdrawal. | 2001 Feb |
|
A model of atypical absence seizures: EEG, pharmacology, and developmental characterization. | 2001 Feb 13 |
|
Baclofen antagonises intravenous self-administration of gamma-hydroxybutyric acid in mice. | 2001 Jul 20 |
|
Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2001 Jul-Aug |
|
Response to the presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids. | 2001 Jul-Aug |
|
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate. | 2001 Jun 12 |
|
Effect of storage temperature on endogenous GHB levels in urine. | 2001 Jun 15 |
|
[Liquid ecstasy poisoning: study of 22 cases]. | 2001 Jun 16 |
|
The first case of 4-hydroxybutyric aciduria in Japan. | 2001 Mar |
|
Lack of efficacy of benzodiazepines in treating gamma-hydroxybutyrate withdrawal. | 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 |
|
1H NMR spectroscopic investigation of serum and urine in a case of acute tetrahydrofuran poisoning. | 2001 May-Jun |
|
Drug dependence studies and regulations: an overview of the past and present. | 2001 Nov |
|
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice. | 2001 Nov |
|
Window of detection of gamma-hydroxybutyrate in blood and saliva. | 2001 Nov |
|
Characteristics of pregnant women who use ecstasy (3, 4-methylenedioxymethamphetamine). | 2001 Nov-Dec |
|
[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 |
|
[Well-documented information on GHB]. | 2001 Oct 3 |
|
Discrimination of gamma-hydroxybutyrate and ethanol administered separately and as a mixture in rats. | 2001 Sep |
|
GHB. Club drug or confusing artifact? | 2001 Sep |
|
The use of physostigmine in the management of gamma-hydroxybutyrate overdose. | 2001 Sep |
|
Two cases of withdrawal from 1,4-Butanediol use. | 2001 Sep |
|
Prolonged withdrawal from extreme gamma-hydroxybutyrate (GHB) abuse. | 2001 Sep-Oct |
|
Huntingtin is present in the nucleus, interacts with the transcriptional corepressor C-terminal binding protein, and represses transcription. | 2002 Mar 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://pp.jazzpharma.com/pi/xyrem.en.USPI.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11313294
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.
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ACTIVE MOIETY
SUBSTANCE RECORD