関: barbital

WordNet

a barbiturate used as a hypnotic (同)veronal, barbitone, diethylbarbituric acid, diethylmalonylurea

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ベロナール(睡眠薬の商標名)
バルビタール(催眠剤に用いられる)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/05/27 08:45:32」(JST)

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Barbital (as known in the United States) or barbitone (as known elsewhere), marketed under the brand names Veronal for the pure acid and Medinal for the sodium salt, was the first commercially available barbiturate. It was used as a sleeping aid (hypnotic) from 1903 until the mid-1950s. The chemical names for barbitone are diethylmalonyl urea or diethylbarbituric acid; hence, the sodium salt (known as medinal, a genericised trademark in the United Kingdom), is known also as sodium diethylbarbiturate. Barbitone was prepared by condensing diethylmalonic ester with urea in the presence of sodium ethoxide, and then by adding at least two molar equivalents of ethyl iodide to the silver salt of malonylurea or possibly to a basic solution of the acid. The result was an odorless, slightly bitter, white crystalline powder.

Synthesis [edit]

Barbitone was first synthesized in 1902 by German chemists Emil Fischer and Joseph von Mering. They published their discovery in 1903 and it was marketed in 1904 by the Bayer company as “Veronal”. A soluble salt of barbitone was marketed by the Schering company as “Medinal.” It was dispensed for “insomnia induced by nervous excitability”.^[1]^{[unreliable source?]} It was provided in either capsules or cachets. The therapeutic dose was ten to fifteen grains (0.65-0.97 grams). 3.5 to 4.4 grams is the deadly dose but sleep has also been prolonged up to ten days with recovery.

Barbitone can be synthesized in a condensation reaction from urea and a diethyl malonate derivative:

Pharmacology [edit]

Barbitone was considered to be a great improvement over the existing hypnotics. Its taste was slightly bitter, but an improvement over the strong, unpleasant taste of the commonly used bromides. It had few side effects. Its therapeutic dose was far below the toxic dose. However, prolonged usage resulted in tolerance to the drug, requiring higher doses to reach the desired effect. Fatal overdoses of this slow acting hypnotic were not uncommon.

References [edit]

Fischer, Emil and Joseph von Mering, “Ueber eine neue Klasse von Schlafmitteln”, Therap Gegenw 44:97-101, 1903.
"Veronal", in Finley, Ellingwood, M.D. The American Materia Medica, Therapeutics and Pharmacognosy", 1919. [2], accessed 07 Nov 2005.

^ [1]

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.

Bibliography [edit]

(English) Dombrowski SM, Krishnan R, Witte M,Maitra S, Diesing C, et al. 1998. Constitutive and barbital-induced expression of the CYP6A2 allele of a high producerstrain of CYP6A2 in the genetic backgroundof a low producer strain. Gene221:69–77.

English Journal

Improvement and validation of a medium-term gpt delta rat model for predicting chemical carcinogenicity and underlying mode of action.

Matsushita K1, Kuroda K1, Ishii Y1, Takasu S1, Kijima A1, Kawaguchi H2, Miyoshi N2, Nohmi T3, Ogawa K1, Nishikawa A3, Umemura T4.
Experimental and toxicologic pathology : official journal of the Gesellschaft für Toxikologische Pathologie.Exp Toxicol Pathol.2014 Sep;66(7):313-21. doi: 10.1016/j.etp.2014.05.002. Epub 2014 Jun 11.
We have developed a new medium-term animal model, "GPG", in which an in vivo mutation assay in partially hepatectomized tissue and a tumor-promoting assay were performed. The tumor-promoting assay measures glutathione S-transferase placental form positive foci induced by diethylnitrosamine (DEN) in
PMID 24929978

Crystal polymorphs of barbital: news about a classic polymorphic system.

Zencirci N1, Griesser UJ, Gelbrich T, Apperley DC, Harris RK.
Molecular pharmaceutics.Mol Pharm.2014 Jan 6;11(1):338-50. doi: 10.1021/mp400515f. Epub 2013 Dec 11.
Barbital is a hypnotic agent that has been intensely studied for many decades. The aim of this work was to establish a clear and comprehensible picture of its polymorphic system. Four of the six known solid forms of barbital (denoted I(0), III, IV, and V) were characterized by various analytical tec
PMID 24283960

Urethane suppresses renal sympathetic nerve activity in Wistar rats.

Wang GF1, Mao XJ, Chen ZJ.
European review for medical and pharmacological sciences.Eur Rev Med Pharmacol Sci.2014;18(10):1454-7.
AIM: To investigate the effects of urethane on renal sympathetic nerve activity (RSNA) in Wistar rats.MATERIALSAND METHODS: 46 rats were randomly allocated in two groups: group A in which rats were injected with urethane; group B in which barbital sodium was used as a control. The changes of RSNA, b
PMID 24899602

「barbital」

Barbital
Systematic (IUPAC) name
	5,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682221
Pregnancy cat.	?
Legal status	Schedule IV (US)
Routes	Oral
Pharmacokinetic data
Half-life	30.3 (± 3.2) hours
Identifiers
CAS number	57-44-3
ATC code	N05CA04
PubChem	CID 2294
DrugBank	DB01483
ChemSpider	2206
UNII	5WZ53ENE2P
KEGG	D01740
ChEBI	CHEBI:31252
ChEMBL	CHEMBL444
Chemical data
Formula	C8H12N2O3
Mol. mass	184.193 g/mol
	SMILES O=C1NC(=O)NC(=O)C1(CC)CC;
	InChI 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) ; Key:FTOAOBMCPZCFFF-UHFFFAOYSA-N ;
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