ContaminantDB: Sodium 4-hydroxybutanoate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:51:23 UTC

Update Date

2016-11-09 01:16:08 UTC

Accession Number

CHEM020157

Identification

Common Name

Sodium 4-hydroxybutanoate

Class

Small Molecule

Description

Sodium oxybate (Xyrem) is a central nervous system depressant used for the treatment of cataplexy and extreme daytime sleepiness (EDS) associated with narcolepsy. It is the sodium salt of gamma hydroxybutyric acid (GHB) which is an endogenous compound and a metabolite of the neurotransmitter GABA. The exact mechanism of action for treating EDS and cataplexy is not known but is is hypothesised that its therapeutic effects are due to GABA(B) effects on noradrenergic, dopaminaergic and thalamocorticol neurons. The drug follows non-linear pharmacokinetics. As it has been associated with misuse/abuse it is strictly controlled and all patients and prescribers must enroll in the sodium oxybate REMs program in order to gain access to the medication.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Sodium gammahydroxybutyrate	Kegg
Xyrem	Kegg
Sodium gammahydroxybutyric acid	Generator
Sodium oxybic acid	Generator
Sodium;4-hydroxybutanoic acid	Generator
Sodium gamma-hydroxybutyrate	MeSH
Oxybate, sodium	MeSH
Somsanit	MeSH
gamma-Hydroxybutyrate	MeSH
Oxybate sodium	MeSH
gamma Hydroxybutyrate	MeSH
4-Hydroxybutyrate sodium	MeSH
Oxybutyrate, sodium	MeSH
Sodium oxybutyrate	MeSH
4 Hydroxybutyrate sodium	MeSH
Sodium oxybate	MeSH
Sodium gamma hydroxybutyrate	MeSH
Sodium 4-hydroxybutanoic acid	Generator

Chemical Formula

C₄H₇NaO₃

Average Molecular Mass

126.087 g/mol

Monoisotopic Mass

126.029 g/mol

CAS Registry Number

502-85-2

IUPAC Name

sodium 4-hydroxybutanoate

Traditional Name

sodium gamma-hydroxybutyrate

SMILES

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

InChI Identifier

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

InChI Key

XYGBKMMCQDZQOZ-UHFFFAOYSA-M

Chemical Taxonomy

Description

belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Short-chain hydroxy acids and derivatives

Direct Parent

Short-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Short-chain hydroxy acid
Fatty acid
Carboxylic acid salt
Organic alkali metal salt
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic sodium salt
Organic oxide
Organic salt
Organic zwitterion
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	660 g/L	ALOGPS
logP	-0.34	ALOGPS
logP	-0.51	ChemAxon
logS	0.72	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.64 m³·mol⁻¹	ChemAxon
Polarizability	9.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fur-9000000000-63fc3a3c55b7d5bcf1dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9300000000-1b69010c667300ade742	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ku-9000000000-9c4e198bb0b0af1f0ccd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-0bb06f9e1c0e09fe0ac1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9400000000-b019e1f43f01081eadbd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-9100000000-19c4985189324454e93c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-9000000000-7e4fdfe71ae6fc5af2a2	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09072

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Sodium oxybate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

10412

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Sodium 4-hydroxybutanoate (CHEM020157)

Structure for CHEM020157: Sodium 4-hydroxybutanoate