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
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
Evidence for a G protein-coupled gamma-hydroxybutyric acid receptor.
2000 Nov
Circuit party attendance, club drug use, and unsafe sex in gay men.
2001
Properties, modifications and applications of biopolyesters.
2001
The many faces of ecstasy.
2001 Apr
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
A comprehensive review of MDMA and GHB: two common club drugs.
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
Lack of genetic differentiation among widely spaced subpopulations of a butterfly with home range behaviour.
2001 Feb
Gamma-hydroxybutyrate withdrawal syndrome.
2001 Feb
Dansylation of hydroxyl and carboxylic acid functional groups.
2001 Feb 26
Perturbation of rat renal tubule transport of the organic cation amantadine in recent onset streptozotocin-induced diabetes and in uninephrectomy.
2001 Jan
Gamma-hydroxybutyrate overdose and physostigmine: teaching new tricks to an old drug?
2001 Jan
Adverse events, including death, associated with the use of 1,4-butanediol.
2001 Jan 11
Expression of a glutamate decarboxylase homologue is required for normal oxidative stress tolerance in Saccharomyces cerevisiae.
2001 Jan 5
GHB and driving impairment.
2001 Jul
A case of withdrawal from the GHB precursors gamma-butyrolactone and 1,4-butanediol.
2001 Jul
[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
It's a rave new world: rave culture and illicit drug use in the young.
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 urinary excretion of gamma-hydroxybutyric acid in man.
2001 Mar
Assessment of coronary reperfusion in patients with myocardial infarction using fatty acid binding protein concentrations in plasma.
2001 Mar
[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
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
1H NMR spectroscopic investigation of serum and urine in a case of acute tetrahydrofuran poisoning.
2001 May-Jun
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.
2001 Nov
[Autotrophic synthesis of polyalkanoates by Alcaligenes eutrophus in presence of carbon monoxide].
2001 Nov-Dec
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
[Well-documented information on GHB].
2001 Oct 3
Drugs, drink'n and smok'n. Part II.
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
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

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
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
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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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LOINC 28041-2
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LOINC 28065-1
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FDA ORPHAN DRUG 26387
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LOINC 28038-8
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FDA ORPHAN DRUG 85894
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LOINC 29868-7
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NDF-RT N0000175758
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LOINC 47542-6
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LOINC 43198-1
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DEA NO. 2010
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LOINC 50148-6
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LOINC 43197-3
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NDF-RT N0000175728
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LOINC 46085-7
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NDF-RT N0000008501
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LOINC 68441-5
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Code System Code Type Description
PUBCHEM
10413
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PRIMARY
EVMPD
SUB32656
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EPA CompTox
DTXSID2074740
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PRIMARY
CHEBI
16724
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PRIMARY
RXCUI
2387302
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PRIMARY
SMS_ID
100000125890
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PRIMARY
WIKIPEDIA
GAMMA-HYDROXYBUTYRIC ACID
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PRIMARY
CHEBI
30830
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PRIMARY
FDA UNII
30IW36W5B2
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PRIMARY
DAILYMED
30IW36W5B2
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PRIMARY
MESH
C111420
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IUPHAR
4711
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PRIMARY
HSDB
6927
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PRIMARY
CAS
591-81-1
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PRIMARY
MERCK INDEX
m6124
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PRIMARY Merck Index
DRUG BANK
DB01440
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PRIMARY
NCI_THESAURUS
C61773
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PRIMARY
RXCUI
1546380
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ALTERNATIVE RxNorm