BARBITAL

US Previously Marketed

First marketed in 1903

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H12N2O3
Molecular Weight	184.1925
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(CC)C(=O)NC(=O)NC1=O

InChI

InChIKey=FTOAOBMCPZCFFF-UHFFFAOYSA-N

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

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 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
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
Stability of thiopental and pentobarbital in human plasma determined with a new easy and specific gas chromatography-mass spectrometry assay.	1999 Aug	10483614
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
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
Biochemical mechanism of the effect of barbital on rifamycin B biosynthesis by Amycolatopsis mediterranei (M18 strain).	2003	16233407
Complexation of phenolic guests by endo- and exo-hydrogen-bonded receptors.	2003 Jul 21	12956083
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
Heme oxygenase, aminolevulinate acid synthetase and the antioxidant system in the brain of mice treated with porphyrinogenic drugs.	2005 Oct 3	16309571
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
Analysis of C4 and the C4 binding protein in the MRL/lpr mouse.	2007	17971229
Proximal visceral endoderm and extraembryonic ectoderm regulate the formation of primordial germ cell precursors.	2007 Dec 20	18096072
Modulation of the complement system by human beta-defensin 2.	2007 Jan 10	17235375
Deletion of complement factor H-related genes CFHR1 and CFHR3 is associated with atypical hemolytic uremic syndrome.	2007 Mar 16	17367211
Surviving mousepox infection requires the complement system.	2008 Dec	19112490
Application of two different kinds of sera against the Proteus penneri lipopolysaccharide core region in search of epitopes determining cross-reactions with antibodies.	2008 Mar-Apr	18373243
EspJ of enteropathogenic and enterohaemorrhagic Escherichia coli inhibits opsono-phagocytosis.	2008 May	18201246
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
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
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
Combination of pneumococcal surface protein A (PspA) with whole cell pertussis vaccine increases protection against pneumococcal challenge in mice.	2010 May 27	20523738
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.

Name

Type

Language

BARBITAL

Official Name

English

BARBITAL [MART.]

Common Name

English

BARBITAL [VANDF]

Common Name

English

BARBITAL [MI]

Common Name

English

BARBITAL [EP IMPURITY]

Common Name

English

barbital [INN]

Common Name

English

5,5-DIETHYLBARBITURIC ACID

Systematic Name

English

BARBITAL [JAN]

Common Name

English

NSC-31352

Code

English

BARBITAL [EP MONOGRAPH]

Common Name

English

BARBITONE

Common Name

English

Barbital [WHO-DD]

Common Name

English

Classification Tree Code System Code

DEA NO.

2145