U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of OXYBATE

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)

HIDE SMILES / InChI

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.

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

1.02677761E12
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
Circuit party attendance, club drug use, and unsafe sex in gay men.
2001
The effect of gamma hydroxybutyrate on serum osmolality.
2001
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
[Gamma hydroxy butyrate intoxication].
2001 Dec
A comprehensive review of MDMA and GHB: two common club drugs.
2001 Dec
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison.
2001 Dec 1
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
[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
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
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
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate.
2001 Jun 12
[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
[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
Lack of efficacy of benzodiazepines in treating gamma-hydroxybutyrate withdrawal.
2001 May
GHB: an important pharmacologic and clinical update.
2001 May-Aug
Inheritance pattern of RAPD markers in Melipona quadrifasciata (Hymenoptera: Apidae, Meliponinae).
2001 May-Jun
Traumatic brain injury after a motor vehicle accident: fact or "fantasy"?
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
Window of detection of gamma-hydroxybutyrate in blood and saliva.
2001 Nov
The Na(+)/H(+) exchange inhibitor eniporide as an adjunct to early reperfusion therapy for acute myocardial infarction. Results of the evaluation of the safety and cardioprotective effects of eniporide in acute myocardial infarction (ESCAMI) trial.
2001 Nov 15
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
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
Role of GABA(B) receptors in the sedative/hypnotic effect of gamma-hydroxybutyric acid.
2001 Oct 12
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.
2001 Oct 15
Elevation of AKR7A2 (succinic semialdehyde reductase) in neurodegenerative disease.
2001 Oct 19
[Well-documented information on GHB].
2001 Oct 3
Drugs, drink'n and smok'n. Part II.
2001 Sep
Discrimination of gamma-hydroxybutyrate and ethanol administered separately and as a mixture in rats.
2001 Sep
GHB. Club drug or confusing artifact?
2001 Sep
Use of physostigmine in the management of gamma-hydroxybutyrate overdose.
2001 Sep
Two cases of withdrawal from 1,4-Butanediol use.
2001 Sep
[GHB--dangerous, addictive and uncontrollable "party drug"].
2001 Sep 19
Prolonged withdrawal from extreme gamma-hydroxybutyrate (GHB) abuse.
2001 Sep-Oct
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

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 Wed Jul 05 22:40:20 UTC 2023
Edited
by admin
on Wed Jul 05 22:40:20 UTC 2023
Record UNII
30IW36W5B2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-HYDROXYBUTANOIC ACID
Preferred Name English
OXYBATE
Common Name English
GAMMA-HYDROXYBUTYRIC ACID [HSDB]
Common Name English
4-HYDROXYBUTYRIC ACID
Systematic Name English
.GAMMA.-HYDROXYBUTYRATE [MI]
Common Name English
.GAMMA.-HYDROXYBUTYRATE
MI  
Systematic Name English
Gamma-hydroxybutyrate [WHO-DD]
Common Name English
GHB
Common Name English
.GAMMA.-HYDROXYBUTYRIC ACID
Systematic Name English
GAMMA HYDROXYBUTYRATE
Systematic Name English
GAMMA-HYDROXYBUTYRIC ACID
HSDB  
Systematic Name English
GAMMA-HYDROXYBUTYRATE
WHO-DD  
Systematic Name English
GAMMA HYDROXYBUTYRIC ACID
Systematic Name English
4-HYDROXYBUTYRATE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 621757
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
NCI_THESAURUS C687
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
FDA ORPHAN DRUG 5384
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
FDA ORPHAN DRUG 694619
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LIVERTOX NBK548588
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 59209-7
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 28041-2
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 28065-1
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
FDA ORPHAN DRUG 26387
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 28038-8
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
FDA ORPHAN DRUG 85894
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 29868-7
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 74920-0
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
NDF-RT N0000175758
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 47542-6
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 43198-1
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
DEA NO. 2010
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 50148-6
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 72433-6
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 43197-3
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LOINC 44358-0
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
NDF-RT N0000175728
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 46085-7
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
NDF-RT N0000008501
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 68441-5
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 57746-0
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 68970-3
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 28044-6
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 68440-7
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
LOINC 43194-0
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
Code System Code Type Description
PUBCHEM
10413
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
EVMPD
SUB32656
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID2074740
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
CHEBI
16724
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
RXCUI
2387302
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
SMS_ID
100000125890
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
WIKIPEDIA
GAMMA-HYDROXYBUTYRIC ACID
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
CHEBI
30830
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
FDA UNII
30IW36W5B2
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
DAILYMED
30IW36W5B2
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
MESH
C111420
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
IUPHAR
4711
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
HSDB
6927
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
CAS
591-81-1
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
MERCK INDEX
M6124
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB01440
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
NCI_THESAURUS
C61773
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
PRIMARY
RXCUI
1546380
Created by admin on Wed Jul 05 22:40:20 UTC 2023 , Edited by admin on Wed Jul 05 22:40:20 UTC 2023
ALTERNATIVE RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
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.
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
succinic semialdehyde dehydrogenase converts succinic semialdehyde to succinic acid
METABOLITE -> PARENT
nitiated by the action of GHB dehydrogenase
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.
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY