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Details

Stereochemistry ACHIRAL
Molecular Formula C4H8O3
Molecular Weight 104.1045
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYBUTANOIC ACID

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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
100.0 µM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.
2001
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
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
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.
2001 Aug
A comprehensive review of MDMA and GHB: two common club drugs.
2001 Dec
Lack of genetic differentiation among widely spaced subpopulations of a butterfly with home range behaviour.
2001 Feb
GHB and driving impairment.
2001 Jul
A case of withdrawal from the GHB precursors gamma-butyrolactone and 1,4-butanediol.
2001 Jul
Drug-facilitated date rape.
2001 Jul 10
Multivariate curve resolution of wavelet and Fourier compressed spectra.
2001 Jul 15
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
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
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
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
[Acute involuntary intoxication with gamma-hydroxybutyric acid].
2001 May
[Gamma-hydroxybutyric acid-ethanolamide (LK 544). The suitability of LK 544 for sedation of patients in intensive care in comparison with midazolam].
2001 May
Lack of efficacy of benzodiazepines in treating gamma-hydroxybutyrate withdrawal.
2001 May
Blood, brain, and hair GHB concentrations following fatal ingestion.
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
GHB: an important pharmacologic and clinical update.
2001 May-Aug
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
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
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors.
2001 Nov 2
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase.
2001 Oct
[Well-documented information on GHB].
2001 Oct 3
Drugs, drink'n and smok'n. Part II.
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
[GHB--dangerous, addictive and uncontrollable "party drug"].
2001 Sep 19
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
Purification and characterization of the D-beta-hydroxybutyrate dehydrogenase from dromedary liver mitochondria.
2002 Jan
Patents

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:25:58 UTC 2019
Edited
by admin
on Mon Oct 21 21:25:58 UTC 2019
Record UNII
30IW36W5B2
Record Status Validated (UNII)
Record Version
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Name Type Language
4-HYDROXYBUTANOIC ACID
Systematic 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
GHB
Common Name English
.GAMMA.-HYDROXYBUTYRIC ACID
Systematic Name English
GAMMA HYDROXYBUTYRATE
Systematic Name English
GAMMA-HYDROXYBUTYRATE [WHO-DD]
Common Name English
GAMMA-HYDROXYBUTYRIC ACID
HSDB  
Systematic Name English
OXYBATE
Common 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 Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
NCI_THESAURUS C687
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
FDA ORPHAN DRUG 5384
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
LIVERTOX 724
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
FDA ORPHAN DRUG 26387
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
FDA ORPHAN DRUG 85894
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
NDF-RT N0000175758
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
DEA NO. 2010
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
NDF-RT N0000175728
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
NDF-RT N0000008501
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
Code System Code Type Description
PUBCHEM
10413
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
EVMPD
SUB32656
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
EPA CompTox
591-81-1
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
WIKIPEDIA
GAMMA-HYDROXYBUTYRIC ACID
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
MESH
C111420
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
IUPHAR
4711
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
HSDB
591-81-1
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
CAS
591-81-1
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
MERCK INDEX
M6124
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY Merck Index
DRUG BANK
DB01440
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
NCI_THESAURUS
C61773
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY
RXCUI
1546380
Created by admin on Mon Oct 21 21:25:58 UTC 2019 , Edited by admin on Mon Oct 21 21:25:58 UTC 2019
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
succinic semialdehyde dehydrogenase converts succinic semialdehyde to succinic acid
METABOLITE -> PARENT
nitiated by the action of GHB dehydrogenase
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY