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
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
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.
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 |
---|---|---|
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
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.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:31:59 GMT 2023
by
admin
on
Sat Dec 16 08:31:59 GMT 2023
|
Record UNII |
R9BHS7060X
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |