LITHIUM OXYBATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H7O3.Li
Molecular Weight	110.038
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HQXIDRLGWYBFQL-UHFFFAOYSA-M

InChI=1S/C4H8O3.Li/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Li
Molecular Weight	6.941
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

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
Huntingtin is present in the nucleus, interacts with the transcriptional corepressor C-terminal binding protein, and represses transcription.	2002-03-01	11739372
Characteristics of pregnant women who use ecstasy (3, 4-methylenedioxymethamphetamine).	2002-01-17	11792525
[Autotrophic synthesis of polyalkanoates by Alcaligenes eutrophus in presence of carbon monoxide].	2002-01-12	11785130
Purification and characterization of the D-beta-hydroxybutyrate dehydrogenase from dromedary liver mitochondria.	2002-01	11742753
Prolonged withdrawal from extreme gamma-hydroxybutyrate (GHB) abuse.	2001-12-12	11739915
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison.	2001-12-01	11707675
[The new drugs: ecstasy, GHB. Update for practitioners].	2001-12	11803792
[Gamma hydroxy butyrate intoxication].	2001-12	11789297
A comprehensive review of MDMA and GHB: two common club drugs.	2001-12	11765302
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.	2001-12	11714906
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.	2001-11-15	11704395
gamma-Hydroxybutyric acid and baclofen decrease extracellular acetylcholine levels in the hippocampus via GABA(B) receptors.	2001-11-02	11711039
Drug dependence studies and regulations: an overview of the past and present.	2001-11	11797422
The chemical interconversion of GHB and GBL: forensic issues and implications.	2001-11	11714141
Traumatic brain injury after a motor vehicle accident: fact or "fantasy"?	2001-11	11696495
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.	2001-11	11682251
Management of gamma-hydroxybutyrate withdrawal.	2001-11	11679881
Window of detection of gamma-hydroxybutyrate in blood and saliva.	2001-11	11673374
Elevation of AKR7A2 (succinic semialdehyde reductase) in neurodegenerative disease.	2001-10-19	11597610
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.	2001-10-15	11587864
Role of GABA(B) receptors in the sedative/hypnotic effect of gamma-hydroxybutyric acid.	2001-10-12	11689189
[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].	2001-10-09	11589102
[Well-documented information on GHB].	2001-10-03	11685765
A contemporaneous finding of fenproporex in a polydrug suicide.	2001-10	11599619
Application of a convenient extraction procedure to analyze gamma-hydroxybutyric acid in fatalities involving gamma-hydroxybutyric acid, gamma-butyrolactone, and 1,4-butanediol.	2001-10	11599603
Pharmacologic rescue of lethal seizures in mice deficient in succinate semialdehyde dehydrogenase.	2001-10	11544478
[Biochemical parameters predictive of neuronal damage in childhood].	2001-09-20	11562846
[Electrophoresis of biologically active substances in the treatment of chronic pancreatitis].	2001-09-20	11561298
[GHB--dangerous, addictive and uncontrollable "party drug"].	2001-09-19	11602959
Drugs, drink'n and smok'n. Part II.	2001-09	11682788
Discrimination of gamma-hydroxybutyrate and ethanol administered separately and as a mixture in rats.	2001-09	11566140
GHB. Club drug or confusing artifact?	2001-09	11563737
gamma-Hydroxybutyrate modulation of glutamate levels in the hippocampus: an in vivo and in vitro study.	2001-09	11553667
The use of physostigmine in the management of gamma-hydroxybutyrate overdose.	2001-09	11547795
Use of physostigmine in the management of gamma-hydroxybutyrate overdose.	2001-09	11524662
Two cases of withdrawal from 1,4-Butanediol use.	2001-09	11524661
Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001-08-15	11501911
Response to the presence of gamma-hydroxybutyric acid (GHB) in postmortem biological fluids.	2001-08-14	11499892
Improved procedure for the analysis of gamma-hydroxybutyrate and ethylene glycol in whole blood.	2001-08-14	11499886
Procedure of bidirectional selective outbreeding for production of two rat lines differing in sensitivity to the sedative/hypnotic effect of gamma-hydroxybutyric acid.	2001-08	11522530
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.	2001-08	11493842
Gamma hydroxybutyrate (GHB) and gamma butyrolactone (GBL) withdrawal: five case studies.	2001-07-31	11476261
Long-term therapy using GHB (sodium gamma hydroxybutyrate) for treatment-resistant chronic alcoholics.	2001-07-31	11476260
Multivariate curve resolution of wavelet and Fourier compressed spectra.	2001-07-15	11476222
Comonomer unit composition and thermal properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)s biosynthesized by Ralstonia eutropha.	2001	11777405
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.	2001	11762678
Gamma-hydroxybutyric acid: patterns of use, effects and withdrawal.	2001	11579621
Circuit party attendance, club drug use, and unsafe sex in gay men.	2001	11547613
The effect of gamma hydroxybutyrate on serum osmolality.	2001	11527239
Using the overlapping parts of laboratory test panels to evaluate abnormal results.	2001	11517622

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 22:08:55 GMT 2025` Edited by `admin` on `Mon Mar 31 22:08:55 GMT 2025`
Record UNII	R9BHS7060X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYBATE LITHIUM

Preferred Name

English

LITHIUM OXYBATE

Common Name

English

BUTANOIC ACID, 4-HYDROXY-, LITHIUM SALT (1:1)

Systematic Name

English

LITHIUM .GAMMA.-HYDROXYBUTYRATE

Systematic Name

English

Oxybate lithium [WHO-DD]

Common Name

English

BUTANOIC ACID, 4-HYDROXY-, MONOLITHIUM SALT

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20979300