Name
Calcium oxybate
Drug Entry
gamma-Hydroxybutyric acid

Gamma hydroxybutyric acid, commonly abbreviated GHB, is a therapeutic drug which is illegal in multiple countries. It is currently regulated in the US and sold by Jazz Pharmaceuticals under the name Xyrem. However, it is important to note that GHB is a designated Orphan drug (in 1985). Today Xyrem is a Schedule III drug; however GHB remains a Schedule I drug and the illicit use of Xyrem falls under penalties of Schedule I. GHB is a naturally occurring substance found in the central nervous system, wine, beef, small citrus fruits and almost all other living creatures in small amounts. It is used illegally under the street names Juice, Liquid Ecstasy or simply G, either as an intoxicant, or as a date rape drug. Xyrem is a central nervous system depressant that reduces excessive daytime sleepiness and cataplexy in patients with narcolepsy.

Accession Number
DBSALT002966  (DB15754)
Structure
Synonyms
Oxybate calcium
UNII
8W24SYD6ZI
CAS Number
82316-97-0
Weight
Average: 246.272
Monoisotopic: 246.0416291
Chemical Formula
C8H14CaO6
InChI Key
AZRRVLSHRWGNRS-UHFFFAOYSA-L
InChI
InChI=1S/2C4H8O3.Ca/c2*5-3-1-2-4(6)7;/h2*5H,1-3H2,(H,6,7);/q;;+2/p-2
IUPAC Name
calcium bis(4-hydroxybutanoate)
SMILES
[Ca++].OCCCC([O-])=O.OCCCC([O-])=O
ChemSpider
2613402
Predicted Properties
PropertyValueSource
Water Solubility21.2 mg/mLALOGPS
logP-0.11ALOGPS
logP-0.51Chemaxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.44Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area60.36 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity34.64 m3·mol-1Chemaxon
Polarizability9.74 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon