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

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
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
Properties, modifications and applications of biopolyesters.
2001
Alteration of GLUR2 expression in the rat brain following absence seizures induced by gamma-hydroxybutyric acid.
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
[The new drugs: ecstasy, GHB. Update for practitioners].
2001 Dec
Lack of genetic differentiation among widely spaced subpopulations of a butterfly with home range behaviour.
2001 Feb
[Drugs and drug abusers].
2001 Feb 17
Dansylation of hydroxyl and carboxylic acid functional groups.
2001 Feb 26
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
[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
Patient information. Date rape drugs: what parents should know.
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
Effect of storage temperature on endogenous GHB levels in urine.
2001 Jun 15
[Liquid ecstasy poisoning: study of 22 cases].
2001 Jun 16
[Biochemical parameters predictive of neuronal damage in childhood].
2001 Jun 16-30
The presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids.
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
[Acute involuntary intoxication with gamma-hydroxybutyric acid].
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
GHB: an important pharmacologic and clinical update.
2001 May-Aug
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
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
Characteristics of pregnant women who use ecstasy (3, 4-methylenedioxymethamphetamine).
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
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
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
Two cases of withdrawal from 1,4-Butanediol use.
2001 Sep
Prolonged withdrawal from extreme gamma-hydroxybutyrate (GHB) abuse.
2001 Sep-Oct
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
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 15:08:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:24 GMT 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 Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
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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LOINC 74920-0
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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 72433-6
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LOINC 43197-3
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LOINC 44358-0
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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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LOINC 57746-0
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LOINC 68970-3
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LOINC 28044-6
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LOINC 68440-7
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LOINC 43194-0
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Code System Code Type Description
PUBCHEM
10413
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
EVMPD
SUB32656
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID2074740
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
CHEBI
16724
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
RXCUI
2387302
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
SMS_ID
100000125890
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
WIKIPEDIA
GAMMA-HYDROXYBUTYRIC ACID
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
CHEBI
30830
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
FDA UNII
30IW36W5B2
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
DAILYMED
30IW36W5B2
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
MESH
C111420
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
IUPHAR
4711
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
HSDB
6927
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
CAS
591-81-1
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
MERCK INDEX
m6124
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB01440
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
NCI_THESAURUS
C61773
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 2023
PRIMARY
RXCUI
1546380
Created by admin on Fri Dec 15 15:08:24 GMT 2023 , Edited by admin on Fri Dec 15 15:08:24 GMT 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
METABOLITE INACTIVE -> PARENT
URINE
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
Too variable to be used as a marker for GHB ingestion.
METABOLITE -> PARENT
succinic semialdehyde dehydrogenase converts succinic semialdehyde to succinic acid
METABOLITE -> PARENT
nitiated by the action of GHB dehydrogenase
METABOLITE -> PARENT
URINE
METABOLITE INACTIVE -> PARENT
Too variable to be used as a marker for GHB ingestion.
URINE
METABOLITE -> PARENT
URINE
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
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY