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

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

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
A recombinant vaccine effectively induces c5a-specific neutralizing antibodies and prevents arthritis.	2010-10-20	20975959
Complement factor H-related proteins CFHR2 and CFHR5 represent novel ligands for the infection-associated CRASP proteins of Borrelia burgdorferi.	2010-10-20	20975954
Modulation of polymorphonuclear neutrophil functions by astrocytes.	2010-09-09	20828397
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.	2010-08-20	20727163
Cell membrane modification for rapid display of bi-functional peptides: a novel approach to reduce complement activation.	2010-07-20	20922044
The virulence protein SopD2 regulates membrane dynamics of Salmonella-containing vacuoles.	2010-07-15	20664790
Complement activation mediates cetuximab inhibition of non-small cell lung cancer tumor growth in vivo.	2010-06-07	20529262
Combination of pneumococcal surface protein A (PspA) with whole cell pertussis vaccine increases protection against pneumococcal challenge in mice.	2010-05-27	20523738
Effects of 17beta-oestradiol and norethisterone acetate on sulfonation and sialylation of gonadotrophins in post-menopausal women.	2010-05	20141368
Inefficient complement system clearance of Trypanosoma cruzi metacyclic trypomastigotes enables resistant strains to invade eukaryotic cells.	2010-03-16	20300530
Annexin-II, DNA, and histones serve as factor H ligands on the surface of apoptotic cells.	2010-02-05	19951950
Determining the reactivity and titre of serum using a haemagglutination assay.	2010-01-29	20118894
Role of genetic polymorphisms in factor H and MBL genes in Tunisian patients with immunoglobulin A nephropathy.	2010	21694925
Some patients with NHL possessed immunoreactivity to gliadin and to cow's milk proteins.	2009-09	19609644
The glyceraldehyde-3-phosphate dehydrogenase and the small GTPase Rab 2 are crucial for Brucella replication.	2009-06	19557163
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.	2009-04	19106233
Brain damage in newborn rat model of meningitis by Enterobacter sakazakii: a role for outer membrane protein A.	2009-03	19139724
Biomass production potential of a wastewater alga Chlorella vulgaris ARC 1 under elevated levels of CO₂and temperature.	2009-02	19333419
Interpain A, a cysteine proteinase from Prevotella intermedia, inhibits complement by degrading complement factor C3.	2009-02	19247445
Complement consumption in children with Plasmodium falciparum malaria.	2009-01-09	19134190
The Staphylococcus aureus protein Sbi acts as a complement inhibitor and forms a tripartite complex with host complement Factor H and C3b.	2008-12	19112495
Surviving mousepox infection requires the complement system.	2008-12	19112490
Foamy macrophages from tuberculous patients' granulomas constitute a nutrient-rich reservoir for M. tuberculosis persistence.	2008-11	19002241
EspJ of enteropathogenic and enterohaemorrhagic Escherichia coli inhibits opsono-phagocytosis.	2008-05	18201246
The different effector function capabilities of the seven equine IgG subclasses have implications for vaccine strategies.	2008-02	17669496
Variability and action mechanism of a family of anticomplement proteins in Ixodes ricinus.	2008-01-02	18167559
The Inactivation of a New Peptidoglycan Hydrolase Pmp23 Leads to Abnormal Septum Formation in Streptococcus pneumoniae.	2008	19088920
Floridoside extracted from the red alga Mastocarpus stellatus is a potent activator of the classical complement pathway.	2008	19005576
Proximal visceral endoderm and extraembryonic ectoderm regulate the formation of primordial germ cell precursors.	2007-12-20	18096072
Metabolization of porphyrinogenic agents in brain: involvement of the phase I drug metabolizing system. A comparative study in liver and kidney.	2007-09	17676386
Application of two different kinds of sera against the Proteus penneri lipopolysaccharide core region in search of epitopes determining cross-reactions with antibodies.	2007-07-24	18373243
Deletion of complement factor H-related genes CFHR1 and CFHR3 is associated with atypical hemolytic uremic syndrome.	2007-03-16	17367211
Modulation of the complement system by human beta-defensin 2.	2007-01-10	17235375
Analysis of C4 and the C4 binding protein in the MRL/lpr mouse.	2007	17971229
Carbonic anhydrase in Tectona grandis: kinetics, stability, isozyme analysis and relationship with photosynthesis.	2006-08	16651256
Deficiency of functional mannose-binding lectin is not associated with infections in patients with systemic lupus erythematosus.	2006	17166254
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
The history of barbiturates a century after their clinical introduction.	2005-12	18568113
Rescue of heterochromatin organization in Hutchinson-Gilford progeria by drug treatment.	2005-11	16261260
Binding of small guest molecules to multivalent receptors.	2005-10-14	16209590
Heme oxygenase, aminolevulinate acid synthetase and the antioxidant system in the brain of mice treated with porphyrinogenic drugs.	2005-10-03	16309571
Selective self-organization of guest molecules in self-assembled molecular boxes.	2005-09-14	16144420
Biochemical mechanism of the effect of barbital on rifamycin B biosynthesis by Amycolatopsis mediterranei (M18 strain).	2003	16233407
Induction of CYP2B1 mediated pentoxyresorufin O-dealkylase activity in different species, sex and tissue by prototype 2B1-inducers.	1995-03-30	7697745
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.	1989-04	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.	1989-01	2910521
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.	1988-12	3206528
Drugs as allergens: the molecular basis of IgE binding to thiopentone.	1987	3654008
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.	1985-02	3856057
Modifying potential of thirty-one chemicals on the short-term development of gamma-glutamyl transpeptidase-positive foci in diethylnitrosamine-initiated rat liver.	1984-10	6150874

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 `Mon Mar 31 17:35:20 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:20 GMT 2025`
Record UNII	5WZ53ENE2P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BARBITAL

Official Name

English

NSC-31352

Preferred 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

BARBITAL [EP MONOGRAPH]

Common Name

English

BARBITONE

Common Name

English

Barbital [WHO-DD]

Common Name

English

Classification Tree Code System Code

DEA NO.

2145