BARBITAL SODIUM

US Previously Marketed

First marketed in 1903

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H11N2O3.Na
Molecular Weight	206.1743
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCC1(CC)C(=O)NC(=O)[N-]C1=O

InChI

InChIKey=RGHFKWPGWBFQLN-UHFFFAOYSA-M

InChI=1S/C8H12N2O3.Na/c1-3-8(4-2)5(11)9-7(13)10-6(8)12;/h3-4H2,1-2H3,(H2,9,10,11,12,13);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C8H12N2O3
Molecular Weight	184.1925
Charge	0
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27086450 | https://www.ncbi.nlm.nih.gov/pubmed/18568113 | https://www.ncbi.nlm.nih.gov/pubmed/16609694

Barbital, the one of the series of barbiturates, has hypnotic, sedative, and anticonvulsant properties and used under the trade name Veronal. It calmed manic patients and helped melancholic patients to sleep and was an effective inducer of sleep in insomniacs, but at the same time compound could induced dependence. It was substituted by the butyl analog, butobarbital, which was three times stronger and its period of action was much shorter due to its lipophilicity. Barbital is a ligand of GABA-receptor complex and in addition, it could have another target, a creatine kinase.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA receptor 5 Target ID: GABA receptor Sources: https://www.ncbi.nlm.nih.gov/pubmed/1654164	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18568113	Primary		Approved 8429	Veronal Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
300 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/957863/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BARBITAL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
3860 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/957863/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BARBITAL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/957863/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BARBITAL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
5 g 1 times / day single, oral Studied dose Dose: 5 g, 1 times / day Route: oral Route: single Dose: 5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1163482/	unhealthy, 19 years n = 1 Health Status: unhealthy Condition: drug withdrawal Age Group: 19 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1163482/	Other AEs: Coma... Other AEs: Coma Sources: https://pubmed.ncbi.nlm.nih.gov/1163482/
250 mg 3 times / day multiple, oral Studied dose Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/	unhealthy, median age 44 years n = 35 Health Status: unhealthy Condition: alcohol withdrawal symptoms Age Group: median age 44 years Sex: M+F Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/	Other AEs: Dizziness, Drug intoxication... Other AEs: Dizziness Drug intoxication Euphoric Tiredness Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/

AEs

AE	Dose	Population
Coma	5 g 1 times / day single, oral Studied dose Dose: 5 g, 1 times / day Route: oral Route: single Dose: 5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1163482/	unhealthy, 19 years n = 1 Health Status: unhealthy Condition: drug withdrawal Age Group: 19 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1163482/
Dizziness	250 mg 3 times / day multiple, oral Studied dose Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/	unhealthy, median age 44 years n = 35 Health Status: unhealthy Condition: alcohol withdrawal symptoms Age Group: median age 44 years Sex: M+F Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/
Drug intoxication	250 mg 3 times / day multiple, oral Studied dose Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/	unhealthy, median age 44 years n = 35 Health Status: unhealthy Condition: alcohol withdrawal symptoms Age Group: median age 44 years Sex: M+F Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/
Euphoric	250 mg 3 times / day multiple, oral Studied dose Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/	unhealthy, median age 44 years n = 35 Health Status: unhealthy Condition: alcohol withdrawal symptoms Age Group: median age 44 years Sex: M+F Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/
Tiredness	250 mg 3 times / day multiple, oral Studied dose Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/	unhealthy, median age 44 years n = 35 Health Status: unhealthy Condition: alcohol withdrawal symptoms Age Group: median age 44 years Sex: M+F Population Size: 35 Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 36 UGT1A10 32

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A10 41	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	no
UGT1A8 48	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	no

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	MT-47311	http://www.ahhchemical.com/product/MT-47311.html
Alsachim	3021	http://www.alsachim.com/product-C4096-glo.bal-view.html
Avantor Inc	75835-276	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
BioSynth	W-105467	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-105467.html
ChemMol	49416387	http://www.chemmol.com/chemmol/49416387.html
ChemMol	99111238	http://www.chemmol.com/chemmol/99111238.html
Chemspace	CSSS00000125364	https://chem-space.com/CSSS00000125364
Clearsynth	CS-CX-00150	https://www.clearsynth.com/en/CSCX00150.html
Clearsynth	CS-CX-00151	https://www.clearsynth.com/en/CSCX00151.html
Glentham Life Sciences	GE3805	http://www.glentham.com/products/product/GE3805/
LGC Standards	LGCAMP1721.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1721.00-01
LGC Standards	LGCAMP1721.00-02	https://www.lgcstandards.com/US/en/p/LGCAMP1721.00-02
LGC Standards	LGCFOR1721.00	https://www.lgcstandards.com/US/en/p/LGCFOR1721.00
LGC Standards	MM1721.00	https://www.lgcstandards.com/US/en/p/MM1721.00
Sigma-Aldrich	B-070_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/b070?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	B0300000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/b0300000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	31995_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/31995?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	B0375_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/b0375?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	B8632_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/b8632?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S520447	http://www.smolecule.com/products/s520447
THE BioTek	bt-260935	https://www.thebiotek.com/product/inhibitors/bt-260935
mcule	MCULE-2107172999	https://mcule.com/MCULE-2107172999/

PubMed

Title	Date	PubMed
Modifying potential of thirty-one chemicals on the short-term development of gamma-glutamyl transpeptidase-positive foci in diethylnitrosamine-initiated rat liver.	1984 Oct	6150874
Comparative tumor-promoting activities of phenobarbital, amobarbital, barbital sodium, and barbituric acid on livers and other organs of male F344/NCr rats following initiation with N-nitrosodiethylamine.	1985 Feb	3856057
Effects of sodium salts of phenobarbital and barbital on development of bladder tumors in male F344/NCr rats pretreated with either N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide or N-nitrosobutyl-4-hydroxybutylamine.	1989 Apr	2711390
Promotion by sodium barbital of renal cortical and transitional cell tumors, but not intestinal tumors, in F344 rats given methyl(acetoxymethyl)nitrosamine, and lack of effect of phenobarbital, amobarbital, or barbituric acid on development of either renal or intestinal tumors.	1989 Jan	2910521
Induction of CYP2B1 mediated pentoxyresorufin O-dealkylase activity in different species, sex and tissue by prototype 2B1-inducers.	1995 Mar 30	7697745
Determination of barbiturates in urine by micellar liquid chromatography and direct injection of sample.	1999 Nov	10703988
Mouse skin passage of a Streptococcus pyogenes Tn917 mutant of sagA/pel restores virulence, beta-hemolysis and sagA/pel expression without altering the position or sequence of the transposon.	2001	11801184
Molecular "chaperones" guide the spontaneous formation of a 15-component hydrogen-bonded assembly.	2002 Jul 3	12083900
Secretion of soluble complement inhibitors factor H and factor H-like protein (FHL-1) by ovarian tumour cells.	2002 Nov 4	12402151
Complexation of phenolic guests by endo- and exo-hydrogen-bonded receptors.	2003 Jul 21	12956083
Rescue of heterochromatin organization in Hutchinson-Gilford progeria by drug treatment.	2005 Nov	16261260
Selective self-organization of guest molecules in self-assembled molecular boxes.	2005 Sep 14	16144420
Analysis of C4 and the C4 binding protein in the MRL/lpr mouse.	2007	17971229
Deletion of complement factor H-related genes CFHR1 and CFHR3 is associated with atypical hemolytic uremic syndrome.	2007 Mar 16	17367211
Metabolization of porphyrinogenic agents in brain: involvement of the phase I drug metabolizing system. A comparative study in liver and kidney.	2007 Sep	17676386
The Inactivation of a New Peptidoglycan Hydrolase Pmp23 Leads to Abnormal Septum Formation in Streptococcus pneumoniae.	2008	19088920
The different effector function capabilities of the seven equine IgG subclasses have implications for vaccine strategies.	2008 Feb	17669496
Variability and action mechanism of a family of anticomplement proteins in Ixodes ricinus.	2008 Jan 2	18167559
Foamy macrophages from tuberculous patients' granulomas constitute a nutrient-rich reservoir for M. tuberculosis persistence.	2008 Nov	19002241
Pharmacological profiles of animal- and nonanimal-derived sulfated polysaccharides--comparison of unfractionated heparin, the semisynthetic glucan sulfate PS3, and the sulfated polysaccharide fraction isolated from Delesseria sanguinea.	2009 Apr	19106233
The glyceraldehyde-3-phosphate dehydrogenase and the small GTPase Rab 2 are crucial for Brucella replication.	2009 Jun	19557163
Some patients with NHL possessed immunoreactivity to gliadin and to cow's milk proteins.	2009 Sep	19609644
Role of genetic polymorphisms in factor H and MBL genes in Tunisian patients with immunoglobulin A nephropathy.	2010	21694925
Cell membrane modification for rapid display of bi-functional peptides: a novel approach to reduce complement activation.	2010 Jul 20	20922044
Complement activation mediates cetuximab inhibition of non-small cell lung cancer tumor growth in vivo.	2010 Jun 7	20529262
A recombinant vaccine effectively induces c5a-specific neutralizing antibodies and prevents arthritis.	2010 Oct 20	20975959
Complement factor H-related proteins CFHR2 and CFHR5 represent novel ligands for the infection-associated CRASP proteins of Borrelia burgdorferi.	2010 Oct 20	20975954

Patents

Sample Use Guides

In Vivo Use Guide

10 g two times per day

Route of Administration: Oral

In Vitro Use Guide

It was reported the action of sodium barbital as an inhibitor of rabbit-muscle creatine kinase (CK), which plays a significant role in energy homeostasis in the muscles. The activity of CK underwent a rapid decrease when the concentration of sodium barbital was increased to 8 mmol/L, and the residual activity was about 35% of then active CK. The activity of CK dropped slowly until it was almost 0 when the concentration of sodium barbital was increased to 125 mmol/L. These results indicated that sodium barbital might function as an inhibitor of CK.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:40:40 GMT 2023` Edited by `admin` on `Sat Dec 16 17:40:40 GMT 2023`
Record UNII	275L5M93QS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BARBITAL SODIUM

Official Name

English

barbital sodium [INN]

Common Name

English

BARBITAL SODIUM [VANDF]

Common Name

English

SODIUM BARBITAL

Common Name

English

BARBITAL SODIUM SALT [MI]

Common Name

English

BARBITAL SODIUM SALT

Common Name

English

BARBITAL SODIUM [MART.]

Common Name

English

SODIUM DERIVATIVE OF 5,5-DIETHYLBARBITURIC ACID

Common Name

English

Barbital sodium [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67084