BARBITAL

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Binding Agent 1,064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108	Primary		Approved 8,429	Veronal

C_max

Value	Dose	Co-administered	Analyte	Population
300 μg/mL	200 mg single, oral		BARBITAL plasma	Rattus norvegicus

AUC

Value	Dose	Co-administered	Analyte	Population
3860 μg × h/mL	200 mg single, oral		BARBITAL plasma	Rattus norvegicus

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h	200 mg single, oral		BARBITAL plasma	Rattus norvegicus

Doses

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Dose	Population	Adverse events
5 g 1 times / day single, oral Studied dose	unhealthy, 19 years n = 1	Other AEs: Coma...
250 mg 3 times / day multiple, oral Studied dose	unhealthy, median age 44 years n = 35	Other AEs: Dizziness, Drug intoxication...

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AEs

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AE	Dose	Population
Coma	5 g 1 times / day single, oral Studied dose	unhealthy, 19 years n = 1
Dizziness	250 mg 3 times / day multiple, oral Studied dose	unhealthy, median age 44 years n = 35
Drug intoxication	250 mg 3 times / day multiple, oral Studied dose	unhealthy, median age 44 years n = 35
Euphoric	250 mg 3 times / day multiple, oral Studied dose	unhealthy, median age 44 years n = 35
Tiredness	250 mg 3 times / day multiple, oral Studied dose	unhealthy, median age 44 years n = 35

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 36 UGT1A10 32

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A10 41	inhibitor 3,277	no
UGT1A8 48	inhibitor 3,277	no

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Sourcing

Sourcing

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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

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PubMed

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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
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
Rational design of the first closed coordination capsule with octahedral outer shape.	2004 May 3	15112209

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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.