Calcium Oxybate Monohydrate

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C4H7O3.Ca.H2O
Molecular Weight	264.286
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of Calcium Oxybate Monohydrate

Structure Search

SMILES

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

InChI

InChIKey=BFBCVVOZKQROHM-UHFFFAOYSA-L

InChI=1S/2C4H8O3.Ca.H2O/c2*5-3-1-2-4(6)7;;/h2*5H,1-3H2,(H,6,7);;1H2/q;;+2;/p-2

HIDE SMILES / InChI

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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

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

Molecular Formula	Ca
Molecular Weight	40.078
Charge	2
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 2678		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 8429	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	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
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

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
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
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

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
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
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

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 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2E1 882 CYP3A 214

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP3A 298	inhibitor 3277 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
AN PharmaTech	AN-8743
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
Angene	AGN-PC-0S7IT9
Angene	AGN-PC-0ULPJ7
Aurora Fine Chemicals LLC	A07.164.228	http://online.aurorafinechemicals.com/info?ID=A07.164.228
BOC Sciences	52352-27-9	https://www.bocsci.com/polyhydroxybutyric-acid-cas-52352-27-9-item-432937.html
BlocksMatrix Scientific	128021
Cayman Chemical	9002506
ChemMol	99073257	http://www.chemmol.com/chemmol/99073257.html
ChemMol	99110279	http://www.chemmol.com/chemmol/99110279.html
ChemTik	CTK4G5262
Chemhere	Achem206530
Chemieliva Pharmaceutical Co., Ltd	PBCM1350799
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
Enamine	BBV-75779081
HongKong Chemhere	35054-79-6
HongKong Chemhere	SCA47808
HongKong Chemhere	SCF11184
NCI Plated 2007	84223
NovoSeek	10413
Scientific Exchange	F-434693
Sigma Aldrich	G-001
Smolecule	S528679	http://www.smolecule.com/products/s528679
THE BioTek	bt-268885	https://www.thebiotek.com/product/inhibitors/bt-268885
Tetrahedron	TS01692
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
eMolecules	300010111
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

PubMed

Title	Date	PubMed
Thyrotropin-releasing hormone-induced GH release after cocaine withdrawal in cocaine addicts.	1999 Dec	10657535
Evidence for a G protein-coupled gamma-hydroxybutyric acid receptor.	2000 Nov	11032888
Diagnosis of unsuspected gamma hydroxy-butyrate poisoning by proton NMR.	2001	11762678
Preparation and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) microspheres for the sustained release of 5-fluorouracil.	2001	11352116
New developments in the pharmacotherapy of alcohol dependence.	2001	11268820
The many faces of ecstasy.	2001 Apr	11317061
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
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.	2001 Aug	11493842
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 Dec	11714906
Different control of GH secretion by gamma-amino- and gamma-hydroxy-butyric acid in 4-year abstinent alcoholics.	2001 Feb 1	11164685
Dansylation of hydroxyl and carboxylic acid functional groups.	2001 Feb 26	11245890
Gamma-hydroxybutyrate overdose and physostigmine: teaching new tricks to an old drug?	2001 Jan	11145779
Expression of a glutamate decarboxylase homologue is required for normal oxidative stress tolerance in Saccharomyces cerevisiae.	2001 Jan 5	11031268
A case of withdrawal from the GHB precursors gamma-butyrolactone and 1,4-butanediol.	2001 Jul	11399385
Drug-facilitated date rape.	2001 Jul 10	11468961
Multivariate curve resolution of wavelet and Fourier compressed spectra.	2001 Jul 15	11476222
Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001 Jul-Aug	11501911
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
[Biochemical parameters predictive of neuronal damage in childhood].	2001 Jun 16-30	11562846
The first case of 4-hydroxybutyric aciduria in Japan.	2001 Mar	11248463
Development and validation of a high-performance liquid chromatographic method for the determination of gamma-hydroxybutyric acid in rat plasma.	2001 Mar 5	11254201
[Acute involuntary intoxication with gamma-hydroxybutyric acid].	2001 May	11419242
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
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
Drug dependence studies and regulations: an overview of the past and present.	2001 Nov	11797422
Traumatic brain injury after a motor vehicle accident: fact or "fantasy"?	2001 Nov	11696495
Characteristics of pregnant women who use ecstasy (3, 4-methylenedioxymethamphetamine).	2001 Nov-Dec	11792525
[Autotrophic synthesis of polyalkanoates by Alcaligenes eutrophus in presence of carbon monoxide].	2001 Nov-Dec	11785130
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

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 `Sat Dec 16 19:16:53 GMT 2023` Edited by `admin` on `Sat Dec 16 19:16:53 GMT 2023`
Record UNII	Z3YJ9MZ6J2
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Calcium Oxybate Monohydrate

Common Name

English

Butanoic acid, 4-hydroxy-, calcium salt, hydrate (2:1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

164512924

Created by admin on Sat Dec 16 19:16:53 GMT 2023 , Edited by admin on Sat Dec 16 19:16:53 GMT 2023

PRIMARY

CAS

2425612-41-3

Created by admin on Sat Dec 16 19:16:53 GMT 2023 , Edited by admin on Sat Dec 16 19:16:53 GMT 2023

PRIMARY

FDA UNII

Z3YJ9MZ6J2

Created by admin on Sat Dec 16 19:16:53 GMT 2023 , Edited by admin on Sat Dec 16 19:16:53 GMT 2023

PRIMARY

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Amount:

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					30IW36W5B2

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ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: http://pp.jazzpharma.com/pi/xyrem.en.USPI.pdf | https://www.ncbi.nlm.nih.gov/pubmed/17140279/

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://pp.jazzpharma.com/pi/xyrem.en.USPI.pdf | https://www.ncbi.nlm.nih.gov/pubmed/17140279/

C_max

T_1/2

F_unbound

Drug as perpetrator