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Details

Stereochemistry ACHIRAL
Molecular Formula 2C4H7O3.Ca
Molecular Weight 246.271
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALCIUM OXYBATE

SMILES

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

InChI

InChIKey=AZRRVLSHRWGNRS-UHFFFAOYSA-L
InChI=1S/2C4H8O3.Ca/c2*5-3-1-2-4(6)7;/h2*5H,1-3H2,(H,6,7);/q;;+2/p-2

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 Ca
Molecular Weight 40.078
Charge 2
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
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.
2001
Preparation and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) microspheres for the sustained release of 5-fluorouracil.
2001
New developments in the pharmacotherapy of alcohol dependence.
2001
The many faces of ecstasy.
2001 Apr
Alteration of GLUR2 expression in the rat brain following absence seizures induced by gamma-hydroxybutyric acid.
2001 Apr
Long-term therapy using GHB (sodium gamma hydroxybutyrate) for treatment-resistant chronic alcoholics.
2001 Apr-Jun
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.
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
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
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product.
2001 Feb
[Drugs and drug abusers].
2001 Feb 17
GHB and driving impairment.
2001 Jul
A case of withdrawal from the GHB precursors gamma-butyrolactone and 1,4-butanediol.
2001 Jul
Baclofen antagonises intravenous self-administration of gamma-hydroxybutyric acid in mice.
2001 Jul 20
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
Metabolic flux in cellulose batch and cellulose-fed continuous cultures of Clostridium cellulolyticum in response to acidic environment.
2001 Jun
[Liquid ecstasy poisoning: study of 22 cases].
2001 Jun 16
The presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids.
2001 Mar
GHB: its use and misuse.
2001 Mar
The first case of 4-hydroxybutyric aciduria in Japan.
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
The content and distribution of troponin I, troponin T, myoglobin, and alpha-hydroxybutyric acid dehydrogenase in the human heart.
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
Inheritance pattern of RAPD markers in Melipona quadrifasciata (Hymenoptera: Apidae, Meliponinae).
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
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
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
A contemporaneous finding of fenproporex in a polydrug suicide.
2001 Oct
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase.
2001 Oct
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
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
Comonomer unit composition and thermal properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)s biosynthesized by Ralstonia eutropha.
2001 Winter
Purification and characterization of the D-beta-hydroxybutyrate dehydrogenase from dromedary liver mitochondria.
2002 Jan
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:47:58 GMT 2023
Edited
by admin
on Sat Dec 16 14:47:58 GMT 2023
Record UNII
8W24SYD6ZI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CALCIUM OXYBATE
Common Name English
CALCIUM OXYBATE [ORANGE BOOK]
Common Name English
XYWAV COMPONENT CALCIUM OXYBATE
Brand Name English
Oxybate calcium [WHO-DD]
Common Name English
CALCIUM OXYBATE COMPONENT OF XYWAV
Brand Name English
BUTANOIC ACID, 4-HYDROXY-, CALCIUM SALT (2:1)
Systematic Name English
OXYBATE CALCIUM
Common Name English
Code System Code Type Description
PUBCHEM
3367708
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
RXCUI
2387307
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
DAILYMED
8W24SYD6ZI
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
CAS
82316-97-0
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
279-930-6
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
SMS_ID
300000017597
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
FDA UNII
8W24SYD6ZI
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID201002609
Created by admin on Sat Dec 16 14:47:58 GMT 2023 , Edited by admin on Sat Dec 16 14:47:58 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY