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

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 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18568113	Primary		Approved 8583	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 Health Status: unhealthy Age Group: 19 years Sex: M 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 Health Status: unhealthy Age Group: median age 44 years Sex: M+F 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 Health Status: unhealthy Age Group: 19 years Sex: M 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 Health Status: unhealthy Age Group: median age 44 years Sex: M+F 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 Health Status: unhealthy Age Group: median age 44 years Sex: M+F 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 Health Status: unhealthy Age Group: median age 44 years Sex: M+F 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 Health Status: unhealthy Age Group: median age 44 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6730996/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 37 UGT1A10 37

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A10 46	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	no
UGT1A8 49	inhibitor 4027 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
mcule	MCULE-2107172999	https://mcule.com/MCULE-2107172999/
Sigma-Aldrich	31995_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/31995?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
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	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

PubMed

Title	Date	PubMed
Drugs as allergens: the molecular basis of IgE binding to thiopentone.	1987	3654008
The chronic hepatic or renal toxicity of di(2-ethylhexyl) phthalate, acetaminophen, sodium barbital, and phenobarbital in male B6C3F1 mice: autoradiographic, immunohistochemical, and biochemical evidence for levels of DNA synthesis not associated with carcinogenesis or tumor promotion.	1988 Dec	3206528
Induction of CYP2B1 mediated pentoxyresorufin O-dealkylase activity in different species, sex and tissue by prototype 2B1-inducers.	1995 Mar 30	7697745
The effects of some porphyrinogenic drugs on the brain cholinergic system.	2002 Feb	11929041
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
Supramolecular synthons based on N-H...N and C-H...O hydrogen bonds. Crystal engineering of a helical structure with 5,5-diethylbarbituric acid.	2002 Sep 7	12271630
Isolation and characterization of anticomplementary beta-glucans from the shoots of bamboo Phyllostachys edulis.	2003 Jan	12567280
Rational design of the first closed coordination capsule with octahedral outer shape.	2004 May 3	15112209
The history of barbiturates a century after their clinical introduction.	2005 Dec	18568113
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
Statin-induced expression of CD59 on vascular endothelium in hypoxia: a potential mechanism for the anti-inflammatory actions of statins in rheumatoid arthritis.	2006	16859540
Carbonic anhydrase in Tectona grandis: kinetics, stability, isozyme analysis and relationship with photosynthesis.	2006 Aug	16651256
Modulation of the complement system by human beta-defensin 2.	2007 Jan 10	17235375
The Inactivation of a New Peptidoglycan Hydrolase Pmp23 Leads to Abnormal Septum Formation in Streptococcus pneumoniae.	2008	19088920
The Staphylococcus aureus protein Sbi acts as a complement inhibitor and forms a tripartite complex with host complement Factor H and C3b.	2008 Dec	19112495
Surviving mousepox infection requires the complement system.	2008 Dec	19112490
Variability and action mechanism of a family of anticomplement proteins in Ixodes ricinus.	2008 Jan 2	18167559
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
Biomass production potential of a wastewater alga Chlorella vulgaris ARC 1 under elevated levels of CO₂and temperature.	2009 Feb	19333419
Interpain A, a cysteine proteinase from Prevotella intermedia, inhibits complement by degrading complement factor C3.	2009 Feb	19247445
Complement consumption in children with Plasmodium falciparum malaria.	2009 Jan 9	19134190
The glyceraldehyde-3-phosphate dehydrogenase and the small GTPase Rab 2 are crucial for Brucella replication.	2009 Jun	19557163
Brain damage in newborn rat model of meningitis by Enterobacter sakazakii: a role for outer membrane protein A.	2009 Mar	19139724
Some patients with NHL possessed immunoreactivity to gliadin and to cow's milk proteins.	2009 Sep	19609644
Recombinant human complement component C2 produced in a human cell line restores the classical complement pathway activity in-vitro: an alternative treatment for C2 deficiency diseases.	2010 Aug 20	20727163
Annexin-II, DNA, and histones serve as factor H ligands on the surface of apoptotic cells.	2010 Feb 5	19951950
Determining the reactivity and titre of serum using a haemagglutination assay.	2010 Jan 29	20118894

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.

Name

Type

Language

BARBITAL SODIUM

Official Name

English

BARBITAL SODIUM SALT

Preferred 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 [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