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Details

Stereochemistry ACHIRAL
Molecular Formula 2C4H7O3.Ca.H2O
Molecular Weight 264.286
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Calcium Oxybate Monohydrate

SMILES

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

InChI

InChIKey=BFBCVVOZKQROHM-UHFFFAOYSA-L
InChI=1S/2C4H8O3.Ca.H2O/c2*5-3-1-2-4(6)7;;/h2*5H,1-3H2,(H,6,7);;1H2/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 H2O
Molecular Weight 18.0153
Charge 0
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
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
[The new drugs: ecstasy, GHB. Update for practitioners].
2001 Dec
[Gamma hydroxy butyrate intoxication].
2001 Dec
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison.
2001 Dec 1
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
[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
Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2001 Jul-Aug
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate.
2001 Jun 12
The presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids.
2001 Mar
The urinary excretion of gamma-hydroxybutyric acid in man.
2001 Mar
[Acute involuntary intoxication with gamma-hydroxybutyric acid].
2001 May
A case of severe withdrawal from gamma-hydroxybutyrate.
2001 May
Drug dependence studies and regulations: an overview of the past and present.
2001 Nov
Window of detection of gamma-hydroxybutyrate in blood and saliva.
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
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
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
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
[GHB--dangerous, addictive and uncontrollable "party drug"].
2001 Sep 19
Using the overlapping parts of laboratory test panels to evaluate abnormal results.
2001 Summer
Purification and characterization of the D-beta-hydroxybutyrate dehydrogenase from dromedary liver mitochondria.
2002 Jan
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 19:16:53 GMT 2023
Edited
by admin
on Sat Dec 16 19:16:53 GMT 2023
Record UNII
Z3YJ9MZ6J2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Calcium Oxybate Monohydrate
Common Name English
Butanoic acid, 4-hydroxy-, calcium salt, hydrate (2:1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
164512924
Created by admin on Sat Dec 16 19:16:53 GMT 2023 , Edited by admin on Sat Dec 16 19:16:53 GMT 2023
PRIMARY
CAS
2425612-41-3
Created by admin on Sat Dec 16 19:16:53 GMT 2023 , Edited by admin on Sat Dec 16 19:16:53 GMT 2023
PRIMARY
FDA UNII
Z3YJ9MZ6J2
Created by admin on Sat Dec 16 19:16:53 GMT 2023 , Edited by admin on Sat Dec 16 19:16:53 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY