OXYBATE

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 Search

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

Description
Sources: http://pp.jazzpharma.com/pi/xyrem.en.USPI.pdf | https://www.ncbi.nlm.nih.gov/pubmed/17140279/

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

Primary Target	Pharmacology	Condition	Potency
GABA-B receptor 32 Target ID: CHEMBL2111463 Sources: http://pp.jazzpharma.com/pi/xyrem.en.USPI.pdf	Agonist 2678		100.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Narcolepsy 20 Sources: http://www.mdedge.com/currentpsychiatry/article/66165/sleep-medicine/sodium-oxybate-new-way-treat-narcolepsy	Primary		Approved 8429	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

C_max

Value	Dose	Analyte	Population
54 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1389947	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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

Value	Dose	Analyte	Population
3122 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1389947	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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

T_1/2

Value	Dose	Analyte	Population
27 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1389947	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
99% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8299669	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2E1 882 CYP3A 214

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP3A 298	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1V58
AN PharmaTech	AN-8743
Alfa Chemistry	240255
Alfa Chemistry	ACM2787099
Alfa Chemistry	ACM82316970
Allbio Pharm Co., Ltd	AB00219	http://www.allbiopharm.com/product/n/AB00219
Ambinter	Amb18640332	http://www.ambinter.com/reference/18640332
Angene	AGN-PC-0S7IT9
Angene	AGN-PC-0ULPJ7
Aurora Fine Chemicals LLC	A07.164.228	http://online.aurorafinechemicals.com/info?ID=A07.164.228
BOC Sciences	52352-27-9	https://www.bocsci.com/polyhydroxybutyric-acid-cas-52352-27-9-item-432937.html
BlocksMatrix Scientific	128021
Cayman Chemical	9002506
ChemMol	99073257	http://www.chemmol.com/chemmol/99073257.html
ChemMol	99110279	http://www.chemmol.com/chemmol/99110279.html
ChemTik	CTK4G5262
Chemhere	Achem206530
Chemieliva Pharmaceutical Co., Ltd	PBCM1350799
Clearsynth	CS-DV-02824	https://www.clearsynth.com/en/CSDV02824.html
Compound Cloud	10413
Compound Cloud	23663870
Debye Scientific	DB-071156
Elsa Biotechnology	ELSA20-9313
Enamine	BBV-75779081
HongKong Chemhere	35054-79-6
HongKong Chemhere	SCA47808
HongKong Chemhere	SCF11184
NCI Plated 2007	84223
NovoSeek	10413
Scientific Exchange	F-434693
Sigma Aldrich	G-001
Smolecule	S528679	http://www.smolecule.com/products/s528679
THE BioTek	bt-268885	https://www.thebiotek.com/product/inhibitors/bt-268885
Tetrahedron	TS01692
Toronto Research Chemicals	A101050
Toronto Research Chemicals	D290415
Toronto Research Chemicals	H833015
Toronto Research Chemicals	KIT4995
Toronto Research Chemicals	P839643
ZINC	ZINC000001532805	http://zinc15.docking.org/substances/ZINC000001532805
eMolecules	300010111
iChemical	EBD72572	http://www.ichemical.com/products/591-81-1.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7287616371
mcule	MCULE-8739507548

PubMed

Title	Date	PubMed
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.	2001	11762678
Preparation and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) microspheres for the sustained release of 5-fluorouracil.	2001	11352116
New developments in the pharmacotherapy of alcohol dependence.	2001	11268820
Alteration of GLUR2 expression in the rat brain following absence seizures induced by gamma-hydroxybutyric acid.	2001 Apr	11255072
Gamma hydroxybutyrate (GHB) and gamma butyrolactone (GBL) withdrawal: five case studies.	2001 Apr-Jun	11476261
Long-term therapy using GHB (sodium gamma hydroxybutyrate) for treatment-resistant chronic alcoholics.	2001 Apr-Jun	11476260
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	11522530
[The new drugs: ecstasy, GHB. Update for practitioners].	2001 Dec	11803792
[Gamma hydroxy butyrate intoxication].	2001 Dec	11789297
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison.	2001 Dec 1	11707675
Lack of genetic differentiation among widely spaced subpopulations of a butterfly with home range behaviour.	2001 Feb	11380670
[Drugs and drug abusers].	2001 Feb 17	11252979
GHB and driving impairment.	2001 Jul	11451079
Drug-facilitated date rape.	2001 Jul 10	11468961
Multivariate curve resolution of wavelet and Fourier compressed spectra.	2001 Jul 15	11476222
Baclofen antagonises intravenous self-administration of gamma-hydroxybutyric acid in mice.	2001 Jul 20	11447342
[Electrophoresis of biologically active substances in the treatment of chronic pancreatitis].	2001 Jul-Aug	11561298
Response to the presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids.	2001 Jul-Aug	11499892
Improved procedure for the analysis of gamma-hydroxybutyrate and ethylene glycol in whole blood.	2001 Jul-Aug	11499886
Patient information. Date rape drugs: what parents should know.	2001 Jun	11405617
It's a rave new world: rave culture and illicit drug use in the young.	2001 Jun	11405616
GHB: a new and novel drug of abuse.	2001 Jun 1	11297827
Identification and effects of interaction phytotoxic compounds from exudate of Cistus ladanifer leaves.	2001 Mar	11441449
The urinary excretion of gamma-hydroxybutyric acid in man.	2001 Mar	11291756
The first case of 4-hydroxybutyric aciduria in Japan.	2001 Mar	11248463
Blood, brain, and hair GHB concentrations following fatal ingestion.	2001 May	11373018
Determination of gamma-hydroxybutyrate in water and human urine by solid phase microextraction-gas chromatography/quadrupole ion trap spectrometry.	2001 May	11373009
The content and distribution of troponin I, troponin T, myoglobin, and alpha-hydroxybutyric acid dehydrogenase in the human heart.	2001 May	11345843
Effect of gamma-hydroxybutyric acid on human platelet aggregation in vitro.	2001 May 1	11369419
Selective breeding of two rat lines differing in sensitivity to GHB and baclofen.	2001 May 25	11376602
GHB: an important pharmacologic and clinical update.	2001 May-Aug	11466174
1H NMR spectroscopic investigation of serum and urine in a case of acute tetrahydrofuran poisoning.	2001 May-Jun	11386640
Drug dependence studies and regulations: an overview of the past and present.	2001 Nov	11797422
The chemical interconversion of GHB and GBL: forensic issues and implications.	2001 Nov	11714141
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.	2001 Nov	11682251
Management of gamma-hydroxybutyrate withdrawal.	2001 Nov	11679881
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors.	2001 Nov 2	11711039
Characteristics of pregnant women who use ecstasy (3, 4-methylenedioxymethamphetamine).	2001 Nov-Dec	11792525
[Autotrophic synthesis of polyalkanoates by Alcaligenes eutrophus in presence of carbon monoxide].	2001 Nov-Dec	11785130
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	11599603
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.	2001 Oct 15	11587864
Elevation of AKR7A2 (succinic semialdehyde reductase) in neurodegenerative disease.	2001 Oct 19	11597610
GHB. Club drug or confusing artifact?	2001 Sep	11563737
gamma-Hydroxybutyrate modulation of glutamate levels in the hippocampus: an in vivo and in vitro study.	2001 Sep	11553667
The use of physostigmine in the management of gamma-hydroxybutyrate overdose.	2001 Sep	11547795
Use of physostigmine in the management of gamma-hydroxybutyrate overdose.	2001 Sep	11524662
Two cases of withdrawal from 1,4-Butanediol use.	2001 Sep	11524661
[GHB--dangerous, addictive and uncontrollable "party drug"].	2001 Sep 19	11602959
Using the overlapping parts of laboratory test panels to evaluate abnormal results.	2001 Summer	11517622
Purification and characterization of the D-beta-hydroxybutyrate dehydrogenase from dromedary liver mitochondria.	2002 Jan	11742753

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

In Vitro Use Guide

Unknown

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

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

Systematic Name

English

GAMMA-HYDROXYBUTYRATE

Systematic Name

English

GAMMA HYDROXYBUTYRIC ACID

Systematic Name

English

4-HYDROXYBUTYRATE

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

621757