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

Details

Stereochemistry ACHIRAL
Molecular Formula C4H7O3.Na
Molecular Weight 126.0863
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM OXYBATE

SMILES

[Na+].OCCCC([O-])=O

InChI

InChIKey=XYGBKMMCQDZQOZ-UHFFFAOYSA-M
InChI=1S/C4H8O3.Na/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1

HIDE SMILES / InChI

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

Molecular Formula Na
Molecular Weight 22.9898
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
Evidence for a G protein-coupled gamma-hydroxybutyric acid receptor.
2000 Nov
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.
2001
Circuit party attendance, club drug use, and unsafe sex in gay men.
2001
The effect of gamma hydroxybutyrate on serum osmolality.
2001
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
[The new drugs: ecstasy, GHB. Update for practitioners].
2001 Dec
[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
Gamma-hydroxybutyrate withdrawal syndrome.
2001 Feb
Diazepam in the treatment of GHB dependence.
2001 Feb
A model of atypical absence seizures: EEG, pharmacology, and developmental characterization.
2001 Feb 13
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
Baclofen antagonises intravenous self-administration of gamma-hydroxybutyric acid in mice.
2001 Jul 20
[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
Improved procedure for the analysis of gamma-hydroxybutyrate and ethylene glycol in whole blood.
2001 Jul-Aug
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
[Liquid ecstasy poisoning: study of 22 cases].
2001 Jun 16
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
The urinary excretion of gamma-hydroxybutyric acid in man.
2001 Mar
GHB: its use and misuse.
2001 Mar
The first case of 4-hydroxybutyric aciduria in Japan.
2001 Mar
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
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
Traumatic brain injury after a motor vehicle accident: fact or "fantasy"?
2001 Nov
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors.
2001 Nov 2
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
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
gamma-Hydroxybutyrate modulation of glutamate levels in the hippocampus: an in vivo and in vitro study.
2001 Sep
The use of physostigmine in the management of gamma-hydroxybutyrate overdose.
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
Gamma-hydroxybutyric acid: patterns of use, effects and withdrawal.
2001 Summer
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 Fri Dec 15 15:23:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:00 GMT 2023
Record UNII
7G33012534
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM OXYBATE
EMA EPAR   HSDB   MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
SODIUM OXYBATE COMPONENT OF XYWAV
Brand Name English
CATABATE
Brand Name English
.GAMMA.-HYDROXYBUTYRATE SODIUM SALT [MI]
Common Name English
WY-3478
Code English
SODIUM OXYBATE [USAN]
Common Name English
SODIUM OXYBATE [VANDF]
Common Name English
SODIUM OXYBATE [HSDB]
Common Name English
XYWAV COMPONENT SODIUM OXYBATE
Brand Name English
SODIUM OXYBATE [MART.]
Common Name English
XYREM
Brand Name English
Sodium 4-hydroxybutyrate
Systematic Name English
.GAMMA.-HYDROXYBUTYRATE SODIUM SALT
MI  
Common Name English
SODIUM OXYBATE [ORANGE BOOK]
Common Name English
SODIUM OXYBAT
Common Name English
SODIUM SALT OF GAMMA-HYDROXYBUTYRIC ACID
Common Name English
SODIUM OXYBUTYRATE
Common Name English
SODIUM OXYBATE [EMA EPAR]
Common Name English
Oxybate sodium [WHO-DD]
Common Name English
LUMRYZ
Brand Name English
OXYBATE SODIUM
WHO-DD  
Common Name English
BUTANOIC ACID, 4-HYDROXY-, SODIUM SALT
Common Name English
NSC-84223
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS XYREM (AUTHORIZED: NARCOLEPSY)
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
WHO-VATC QN01AX11
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
WHO-VATC QN07XX04
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
EMA ASSESSMENT REPORTS XYREM (AUTHORIZED: CATAPLEXY)
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
WHO-ATC N01AX11
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
WHO-ATC N07XX04
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
EU-Orphan Drug EU/3/02/131
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
NCI_THESAURUS C2199
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
NDF-RT N0000175758
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
DEA NO. 2012
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
FDA ORPHAN DRUG 530216
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
Code System Code Type Description
MESH
D012978
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
DAILYMED
7G33012534
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
NSC
84223
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
FDA UNII
7G33012534
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
WIKIPEDIA
SODIUM OXYBATE
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL1342
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
CAS
90318-49-3
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
NON-SPECIFIC STOICHIOMETRY
RXCUI
9899
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY RxNorm
HSDB
502-85-2
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
CHEBI
30830
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
LACTMED
Sodium Oxybate
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
PUBCHEM
23663870
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
MERCK INDEX
m6124
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB09072
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-953-3
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID3048940
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
SMS_ID
100000089135
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
EVMPD
SUB14731MIG
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
DRUG CENTRAL
4566
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
CAS
502-85-2
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
NCI_THESAURUS
C61870
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
EVMPD
SUB60580
Created by admin on Fri Dec 15 15:23:00 GMT 2023 , Edited by admin on Fri Dec 15 15:23:00 GMT 2023
PRIMARY
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