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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
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

Primary Target	Pharmacology	Condition	Potency
GABA-B receptor 32	Agonist 2,678		100.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Narcolepsy 20	Primary		Approved 8,429	XYREM

C_max

Value	Dose	Analyte	Population
54 μg/mL	25 mg/kg 2 times / day multiple, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
23 μg/mL	12.5 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
23 μg/mL	25 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
20 μg/mL	50 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3122 μg × min/mL	25 mg/kg 2 times / day multiple, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
905 μg × min/mL	12.5 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
1271 μg × min/mL	25 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
1565 μg × min/mL	50 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
27 min	25 mg/kg 2 times / day multiple, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
20 min	12.5 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
22 min	25 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens
23 min	50 mg/kg single, oral	4-HYDROXYBUTANOIC ACID plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
99%	12.5 mg/kg single, oral		4-HYDROXYBUTANOIC ACID plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 CYP2E1 882 CYP3A 214

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no [IC50 >300 uM]
CYP2C19 1,553	inhibitor 3,277	no [IC50 >300 uM]
CYP2C9 1,819	inhibitor 3,277	no [IC50 >300 uM]
CYP2D6 1,891	inhibitor 3,277	no [IC50 >300 uM]
CYP2E1 970	inhibitor 3,277	no [IC50 >300 uM]

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Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 44 entries

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PubMed

Show entries

Title	Date	PubMed
New developments in the pharmacotherapy of alcohol dependence.	2001	11268820
Properties, modifications and applications of biopolyesters.	2001	11217415
Alteration of GLUR2 expression in the rat brain following absence seizures induced by gamma-hydroxybutyric acid.	2001 Apr	11255072
Long-term therapy using GHB (sodium gamma hydroxybutyrate) for treatment-resistant chronic alcoholics.	2001 Apr-Jun	11476260
[The new drugs: ecstasy, GHB. Update for practitioners].	2001 Dec	11803792

Showing 1 to 5 of 27 entries

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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