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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
Structure of POTASSIUM OXYBATE

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

HIDE SMILES / InChI

Molecular Formula K
Molecular Weight 39.0983
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.

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
The effect of gamma hydroxybutyrate on serum osmolality.
2001
New developments in the pharmacotherapy of alcohol dependence.
2001
Alteration of GLUR2 expression in the rat brain following absence seizures induced by gamma-hydroxybutyric acid.
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
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product.
2001 Feb
Diazepam in the treatment of GHB dependence.
2001 Feb
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
GHB and driving impairment.
2001 Jul
A case of withdrawal from the GHB precursors gamma-butyrolactone and 1,4-butanediol.
2001 Jul
[Electrophoresis of biologically active substances in the treatment of chronic pancreatitis].
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
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
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
[Liquid ecstasy poisoning: study of 22 cases].
2001 Jun 16
[Biochemical parameters predictive of neuronal damage in childhood].
2001 Jun 16-30
The urinary excretion of gamma-hydroxybutyric acid in man.
2001 Mar
GHB: its use and misuse.
2001 Mar
Assessment of coronary reperfusion in patients with myocardial infarction using fatty acid binding protein concentrations in plasma.
2001 Mar
Development and validation of a high-performance liquid chromatographic method for the determination of gamma-hydroxybutyric acid in rat plasma.
2001 Mar 5
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
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
Drug dependence studies and regulations: an overview of the past and present.
2001 Nov
The chemical interconversion of GHB and GBL: forensic issues and implications.
2001 Nov
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
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
A contemporaneous finding of fenproporex in a polydrug suicide.
2001 Oct
Role of GABA(B) receptors in the sedative/hypnotic effect of gamma-hydroxybutyric acid.
2001 Oct 12
Discrimination of gamma-hydroxybutyrate and ethanol administered separately and as a mixture in rats.
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

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 Sat Dec 16 14:54:59 GMT 2023
Edited
by admin
on Sat Dec 16 14:54:59 GMT 2023
Record UNII
S8NKF3H3KT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POTASSIUM OXYBATE
Common Name English
POTASSIUM OXYBATE COMPONENT OF XYWAV
Brand Name English
Oxybate potassium [WHO-DD]
Common Name English
4-HYDROXYBUTANOIC ACID POTASSIUM SALT
Systematic Name English
4-HYDROXYBUTYRIC ACID POTASSIUM SALT
Systematic Name English
POTASSIUM OXYBATE [ORANGE BOOK]
Common Name English
XYWAV COMPONENT POTASSIUM OXYBATE
Brand Name English
BUTANOIC ACID, 4-HYDROXY-, POTASSIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
CAS
57769-01-4
Created by admin on Sat Dec 16 14:54:59 GMT 2023 , Edited by admin on Sat Dec 16 14:54:59 GMT 2023
PRIMARY
PUBCHEM
23689651
Created by admin on Sat Dec 16 14:54:59 GMT 2023 , Edited by admin on Sat Dec 16 14:54:59 GMT 2023
PRIMARY
FDA UNII
S8NKF3H3KT
Created by admin on Sat Dec 16 14:54:59 GMT 2023 , Edited by admin on Sat Dec 16 14:54:59 GMT 2023
PRIMARY
SMS_ID
300000024492
Created by admin on Sat Dec 16 14:54:59 GMT 2023 , Edited by admin on Sat Dec 16 14:54:59 GMT 2023
PRIMARY
DAILYMED
S8NKF3H3KT
Created by admin on Sat Dec 16 14:54:59 GMT 2023 , Edited by admin on Sat Dec 16 14:54:59 GMT 2023
PRIMARY
RXCUI
2387309
Created by admin on Sat Dec 16 14:54:59 GMT 2023 , Edited by admin on Sat Dec 16 14:54:59 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY