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	Ca
Molecular Weight	40.078
Charge	2
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

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

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 2662		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 8360	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 1.02677761E12

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 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2C19 1463 CYP2E1 876 CYP3A 211

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-196_Xyrem_biopharmr_P1.pdf Page: 29, 35	no [IC50 >300 uM]
CYP3A 295	inhibitor 3240 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
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
Properties, modifications and applications of biopolyesters.	2001	11217415
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
Gamma hydroxybutyrate (GHB) and gamma butyrolactone (GBL) withdrawal: five case studies.	2001 Apr-Jun	11476261
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
Lack of genetic differentiation among widely spaced subpopulations of a butterfly with home range behaviour.	2001 Feb	11380670
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product.	2001 Feb	11272308
Different control of GH secretion by gamma-amino- and gamma-hydroxy-butyric acid in 4-year abstinent alcoholics.	2001 Feb 1	11164685
A model of atypical absence seizures: EEG, pharmacology, and developmental characterization.	2001 Feb 13	11171899
[Drugs and drug abusers].	2001 Feb 17	11252979
Dansylation of hydroxyl and carboxylic acid functional groups.	2001 Feb 26	11245890
Perturbation of rat renal tubule transport of the organic cation amantadine in recent onset streptozotocin-induced diabetes and in uninephrectomy.	2001 Jan	11201497
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
[Electrophoresis of biologically active substances in the treatment of chronic pancreatitis].	2001 Jul-Aug	11561298
GHB: a new and novel drug of abuse.	2001 Jun 1	11297827
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate.	2001 Jun 12	11402130
Effect of storage temperature on endogenous GHB levels in urine.	2001 Jun 15	11376982
[Liquid ecstasy poisoning: study of 22 cases].	2001 Jun 16	11446927
GHB: its use and misuse.	2001 Mar	11276153
The first case of 4-hydroxybutyric aciduria in Japan.	2001 Mar	11248463
Assessment of coronary reperfusion in patients with myocardial infarction using fatty acid binding protein concentrations in plasma.	2001 Mar	11179265
Development and validation of a high-performance liquid chromatographic method for the determination of gamma-hydroxybutyric acid in rat plasma.	2001 Mar 5	11254201
Lack of efficacy of benzodiazepines in treating gamma-hydroxybutyrate withdrawal.	2001 May	11396429
Determination of gamma-hydroxybutyrate in water and human urine by solid phase microextraction-gas chromatography/quadrupole ion trap spectrometry.	2001 May	11373009
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
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.	2001 Nov	11682251
[Autotrophic synthesis of polyalkanoates by Alcaligenes eutrophus in presence of carbon monoxide].	2001 Nov-Dec	11785130
A contemporaneous finding of fenproporex in a polydrug suicide.	2001 Oct	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 Oct	11599603
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.	2001 Oct 15	11587864
Elevation of AKR7A2 (succinic semialdehyde reductase) in neurodegenerative disease.	2001 Oct 19	11597610
[GHB--dangerous, addictive and uncontrollable "party drug"].	2001 Sep 19	11602959
Gamma-hydroxybutyric acid: patterns of use, effects and withdrawal.	2001 Summer	11579621
Comonomer unit composition and thermal properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)s biosynthesized by Ralstonia eutropha.	2001 Winter	11777405
Huntingtin is present in the nucleus, interacts with the transcriptional corepressor C-terminal binding protein, and represses transcription.	2002 Mar 1	11739372

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 `Fri Jul 07 00:33:22 UTC 2023` Edited by `admin` on `Fri Jul 07 00:33:22 UTC 2023`
Record UNII	Z3YJ9MZ6J2
Record Status	`Validated (UNII)`
Record Version

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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 Fri Jul 07 00:33:22 UTC 2023 , Edited by admin on Fri Jul 07 00:33:22 UTC 2023

PRIMARY

CAS

2425612-41-3

Created by admin on Fri Jul 07 00:33:22 UTC 2023 , Edited by admin on Fri Jul 07 00:33:22 UTC 2023

PRIMARY

FDA UNII

Z3YJ9MZ6J2

Created by admin on Fri Jul 07 00:33:22 UTC 2023 , Edited by admin on Fri Jul 07 00:33:22 UTC 2023

PRIMARY

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Amount:

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					30IW36W5B2

OXYBATE

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