Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H8O3 |
Molecular Weight | 104.1045 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCCC(O)=O
InChI
InChIKey=SJZRECIVHVDYJC-UHFFFAOYSA-N
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
Molecular Formula | C4H8O3 |
Molecular Weight | 104.1045 |
Charge | 0 |
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 |
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 |
|
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 |
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 |
|
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 |
|
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 |
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 |
|
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 |
|
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 |
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 |
---|---|---|
Circuit party attendance, club drug use, and unsafe sex in gay men. | 2001 |
|
The effect of gamma hydroxybutyrate on serum osmolality. | 2001 |
|
Preparation and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) microspheres for the sustained release of 5-fluorouracil. | 2001 |
|
The many faces of ecstasy. | 2001 Apr |
|
Gamma hydroxybutyrate (GHB) and gamma butyrolactone (GBL) withdrawal: five case studies. | 2001 Apr-Jun |
|
Long-term therapy using GHB (sodium gamma hydroxybutyrate) for treatment-resistant chronic alcoholics. | 2001 Apr-Jun |
|
Procedure of bidirectional selective outbreeding for production of two rat lines differing in sensitivity to the sedative/hypnotic effect of gamma-hydroxybutyric acid. | 2001 Aug |
|
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol. | 2001 Aug |
|
[The new drugs: ecstasy, GHB. Update for practitioners]. | 2001 Dec |
|
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison. | 2001 Dec 1 |
|
Lack of genetic differentiation among widely spaced subpopulations of a butterfly with home range behaviour. | 2001 Feb |
|
GHB and driving impairment. | 2001 Jul |
|
Drug-facilitated date rape. | 2001 Jul 10 |
|
Multivariate curve resolution of wavelet and Fourier compressed spectra. | 2001 Jul 15 |
|
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 |
|
Improved procedure for the analysis of gamma-hydroxybutyrate and ethylene glycol in whole blood. | 2001 Jul-Aug |
|
Patient information. Date rape drugs: what parents should know. | 2001 Jun |
|
It's a rave new world: rave culture and illicit drug use in the young. | 2001 Jun |
|
The Circuit Party Men's Health Survey: findings and implications for gay and bisexual men. | 2001 Jun |
|
Metabolic flux in cellulose batch and cellulose-fed continuous cultures of Clostridium cellulolyticum in response to acidic environment. | 2001 Jun |
|
GHB: a new and novel drug of abuse. | 2001 Jun 1 |
|
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 |
|
[Biochemical parameters predictive of neuronal damage in childhood]. | 2001 Jun 16-30 |
|
Identification and effects of interaction phytotoxic compounds from exudate of Cistus ladanifer leaves. | 2001 Mar |
|
The presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids. | 2001 Mar |
|
[Acute involuntary intoxication with gamma-hydroxybutyric acid]. | 2001 May |
|
[Gamma-hydroxybutyric acid-ethanolamide (LK 544). The suitability of LK 544 for sedation of patients in intensive care in comparison with midazolam]. | 2001 May |
|
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 |
|
The content and distribution of troponin I, troponin T, myoglobin, and alpha-hydroxybutyric acid dehydrogenase in the human heart. | 2001 May |
|
A case of severe withdrawal from gamma-hydroxybutyrate. | 2001 May |
|
Effect of gamma-hydroxybutyric acid on human platelet aggregation in vitro. | 2001 May 1 |
|
Selective breeding of two rat lines differing in sensitivity to GHB and baclofen. | 2001 May 25 |
|
GHB: an important pharmacologic and clinical update. | 2001 May-Aug |
|
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 |
|
Window of detection of gamma-hydroxybutyrate in blood and saliva. | 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 |
|
Application of a convenient extraction procedure to analyze gamma-hydroxybutyric acid in fatalities involving gamma-hydroxybutyric acid, gamma-butyrolactone, and 1,4-butanediol. | 2001 Oct |
|
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase. | 2001 Oct |
|
Elevation of AKR7A2 (succinic semialdehyde reductase) in neurodegenerative disease. | 2001 Oct 19 |
|
Use of physostigmine in the management of gamma-hydroxybutyrate overdose. | 2001 Sep |
|
Two cases of withdrawal from 1,4-Butanediol use. | 2001 Sep |
|
Using the overlapping parts of laboratory test panels to evaluate abnormal results. | 2001 Summer |
|
Comonomer unit composition and thermal properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)s biosynthesized by Ralstonia eutropha. | 2001 Winter |
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
Mon Mar 31 17:47:48 GMT 2025
by
admin
on
Mon Mar 31 17:47:48 GMT 2025
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Record UNII |
30IW36W5B2
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
621757
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NCI_THESAURUS |
C687
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FDA ORPHAN DRUG |
5384
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FDA ORPHAN DRUG |
694619
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LIVERTOX |
NBK548588
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LOINC |
59209-7
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28041-2
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28065-1
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FDA ORPHAN DRUG |
26387
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28038-8
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FDA ORPHAN DRUG |
85894
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29868-7
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74920-0
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NDF-RT |
N0000175758
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47542-6
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43198-1
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DEA NO. |
2010
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50148-6
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10413
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SUB32656
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GAMMA-HYDROXYBUTYRIC ACID
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30830
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m6124
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DB01440
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C61773
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1546380
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ALTERNATIVE | RxNorm |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
|
||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT | |||
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PRECURSOR->PARENT |
GBL is typically marketed for sale as a cleaning solvent or polish. GBL is used as a GHB substitute and as a precursor for clandestine manufacturing of GHB.
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SALT/SOLVATE -> PARENT |
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LABELED -> NON-LABELED | |||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE INACTIVE -> PARENT |
URINE
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||
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT |
URINE
|
||
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METABOLITE -> PARENT |
Too variable to be used as a marker for GHB ingestion.
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METABOLITE -> PARENT |
succinic semialdehyde dehydrogenase converts succinic semialdehyde to succinic acid
|
||
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METABOLITE -> PARENT |
nitiated by the action of GHB dehydrogenase
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||
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METABOLITE -> PARENT |
URINE
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||
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METABOLITE INACTIVE -> PARENT |
Too variable to be used as a marker for GHB ingestion.
URINE
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METABOLITE -> PARENT |
URINE
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PARENT -> METABOLITE ACTIVE |
GBL is readily converted into GHB by the body’s own natural process. Because of this, GBL has similarpharmacological effects to GHB.
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PARENT -> METABOLITE |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
|