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

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

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 2752		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 8583	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	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
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

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
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
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

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
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
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

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 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 CYP2E1 1060 CYP3A 227

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP3A 317	inhibitor 4027 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
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
AN PharmaTech	AN-8743
Angene	AGN-PC-0S7IT9
Angene	AGN-PC-0ULPJ7
Aurora Fine Chemicals LLC	A07.164.228	http://online.aurorafinechemicals.com/info?ID=A07.164.228
BlocksMatrix Scientific	128021
BOC Sciences	52352-27-9	https://www.bocsci.com/polyhydroxybutyric-acid-cas-52352-27-9-item-432937.html
Cayman Chemical	9002506
Chemhere	Achem206530
Chemieliva Pharmaceutical Co., Ltd	PBCM1350799
ChemMol	99073257	http://www.chemmol.com/chemmol/99073257.html
ChemMol	99110279	http://www.chemmol.com/chemmol/99110279.html
ChemTik	CTK4G5262
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
eMolecules	300010111
Enamine	BBV-75779081
HongKong Chemhere	35054-79-6
HongKong Chemhere	SCA47808
HongKong Chemhere	SCF11184
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
NCI Plated 2007	84223
NovoSeek	10413
Scientific Exchange	F-434693
Sigma Aldrich	G-001
Smolecule	S528679	http://www.smolecule.com/products/s528679
Tetrahedron	TS01692
THE BioTek	bt-268885	https://www.thebiotek.com/product/inhibitors/bt-268885
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

PubMed

Title	Date	PubMed
Circuit party attendance, club drug use, and unsafe sex in gay men.	2001	11547613
The effect of gamma hydroxybutyrate on serum osmolality.	2001	11527239
Preparation and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) microspheres for the sustained release of 5-fluorouracil.	2001	11352116
The many faces of ecstasy.	2001 Apr	11317061
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
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.	2001 Aug	11493842
[The new drugs: ecstasy, GHB. Update for practitioners].	2001 Dec	11803792
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
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
Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001 Jul-Aug	11501911
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
The Circuit Party Men's Health Survey: findings and implications for gay and bisexual men.	2001 Jun	11392940
Metabolic flux in cellulose batch and cellulose-fed continuous cultures of Clostridium cellulolyticum in response to acidic environment.	2001 Jun	11390677
GHB: a new and novel drug of abuse.	2001 Jun 1	11297827
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate.	2001 Jun 12	11402130
Effect of storage temperature on endogenous GHB levels in urine.	2001 Jun 15	11376982
[Biochemical parameters predictive of neuronal damage in childhood].	2001 Jun 16-30	11562846
Identification and effects of interaction phytotoxic compounds from exudate of Cistus ladanifer leaves.	2001 Mar	11441449
The presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids.	2001 Mar	11300509
[Acute involuntary intoxication with gamma-hydroxybutyric acid].	2001 May	11419242
[Gamma-hydroxybutyric acid-ethanolamide (LK 544). The suitability of LK 544 for sedation of patients in intensive care in comparison with midazolam].	2001 May	11417267
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
A case of severe withdrawal from gamma-hydroxybutyrate.	2001 May	11326198
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
Inheritance pattern of RAPD markers in Melipona quadrifasciata (Hymenoptera: Apidae, Meliponinae).	2001 May-Jun	11447247
1H NMR spectroscopic investigation of serum and urine in a case of acute tetrahydrofuran poisoning.	2001 May-Jun	11386640
The chemical interconversion of GHB and GBL: forensic issues and implications.	2001 Nov	11714141
Window of detection of gamma-hydroxybutyrate in blood and saliva.	2001 Nov	11673374
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors.	2001 Nov 2	11711039
[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
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase.	2001 Oct	11544478
Elevation of AKR7A2 (succinic semialdehyde reductase) in neurodegenerative disease.	2001 Oct 19	11597610
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
Using the overlapping parts of laboratory test panels to evaluate abnormal results.	2001 Summer	11517622
Comonomer unit composition and thermal properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)s biosynthesized by Ralstonia eutropha.	2001 Winter	11777405

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:48 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:48 GMT 2025`
Record UNII	30IW36W5B2
Record Status	`Validated (UNII)`
Record Version

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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