BUTETHAL SODIUM

US Previously Marketed

First marketed in 1923

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H15N2O3.Na
Molecular Weight	234.2275
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCCCC1(CC)C(=O)NC([O-])=NC1=O

InChI

InChIKey=QTNNCMYRNIXYPH-UHFFFAOYSA-M

InChI=1S/C10H16N2O3.Na/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14;/h3-6H2,1-2H3,(H2,11,12,13,14,15);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C10H16N2O3
Molecular Weight	212.2456
Charge	0
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

Description
Sources: https://www.epharmapedia.com/medicine/profile/162863/Soneryl.html?lang=en&tab=druginfo
Curator's Comment: description was created based on several sources, including: http://www.doctoralia.co.uk/medication/soneryl-10028 | http://www.minclinic.ru/drugs/drugs_eng/S/Soneryl.html

Butethal is a sedative and a hypnotic drug indicated for the treatment of severe intractable insomnia. It acts on receptors in the brain (GABA A receptors) causing the release of the chemical GABA. This chemical inhibits certain areas of the brain resulting in sleepiness. Common side effects are: drowsiness, sedation, unsteadiness, vertigo and inco- ordination. Also, hangover effect, paradoxical excitement, confusion, memory defects and skin rashes. Interactions may occur with the following: adrenocorticoids (cortisone-like medicine), anticoagulants (blood thinners), carbamazepine, corticotropin (barbiturates may decrease the effects of these medicines), central nervous system (CNS) depressants (using these medicines with barbiturates may result in increased CNS depressant effects), divalproex sodium, valproic acid (using these medicines with barbiturates may change the amount of either medicine that you need to take), and oral contraceptives containing estrogens (barbiturates may decrease the effectiveness of these oral contraceptives, and you may need to change to a different type of birth control).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: http://www.minclinic.ru/drugs/drugs_eng/S/Soneryl.html	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.epharmapedia.com/medicine/profile/162863/Soneryl.html?lang=en&tab=druginfo	Primary		Approved 8429	Soneryl Approved Use Soneryl is indicated for the treatment of insomnia.

T_1/2

Value	Dose	Co-administered	Analyte	Population
37.5 h EXPERIMENT https://link.springer.com/article/10.1007/BF00558339	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTETHAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP450 32

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 41	inducer 1573 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/qsar.19900090306 Page: 2.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1MLX
Alsachim	3028	http://www.alsachim.com/product-C4103-glo.bal-view.html
Ambinter	Amb10606518	http://www.ambinter.com/reference/10606518
ChemMol	99151444	http://www.chemmol.com/chemmol/99151444.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0825944
Clearsynth	CS-EK-01344	https://www.clearsynth.com/en/CSEK01344.html
Compound Cloud	6473
Enamine	BBV-78133591
LGC Standards	LGCAMP1625.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1625.00-01
LGC Standards	LGCAMP1625.00-02	https://www.lgcstandards.com/US/en/p/LGCAMP1625.00-02
LGC Standards	LGCFOR1625.00	https://www.lgcstandards.com/US/en/p/LGCFOR1625.00
LGC Standards	MM1625.00	https://www.lgcstandards.com/US/en/p/MM1625.00
NovoSeek	6473
Sinfoo Biotech	S017674	http://www.sinfoobiotech.com/product/1021072
Smolecule	S603084	https://www.smolecule.com/products/s603084
Toronto Research Chemicals	B690105
Toronto Research Chemicals	KIT2335
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0619QA
ZINC	ZINC000005514900	http://zinc15.docking.org/substances/ZINC000005514900
mcule	MCULE-8998219052	https://mcule.com/MCULE-8998219052

PubMed

Title	Date	PubMed
[Acute renal failure caused by ajmaline-butobarbital].	1983 Jun 25	6136033
Effects of MK-801 (dizocilpine) on brain cell membrane function and energy metabolism in experimental Escherichia coli meningitis in the newborn piglet.	2003 Apr	12692422
[A century of barbiturates in neurology].	2004 Oct 16-31	15514906
The history of barbiturates a century after their clinical introduction.	2005 Dec	18568113
5-Butyl-5-ethylbarbituric acid: a phase transition at low temperature.	2005 May	15876720
Epidural abscess caused by Streptococcus milleri in a pregnant woman.	2005 Nov 3	16269087
A polymorph of butobarbital with two distinct hydrogen-bonding motifs.	2007 Dec	18057631
A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women.	2008 Feb-Mar	18818187
40 years hard labour.	2008 May	18711633
The prevalence, incidence and risk factors of herpes simplex virus type 2 infection among pregnant Zimbabwean women followed up nine months after childbirth.	2010 Jan 12	20064273

Patents

Sample Use Guides

In Vivo Use Guide

100-200 mg at bedtime

Route of Administration: Oral

In Vitro Use Guide

Butethal enhanced GABA binding to rat brain synaptosomal membranes in a dose-dependent manner with the threshold concentration at 6.25 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:39:04 UTC 2023` Edited by `admin` on `Sat Dec 16 08:39:04 UTC 2023`
Record UNII	12BJQ6C34C
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUTETHAL SODIUM

Common Name

English

BUTOBARBITAL SODIUM

Systematic Name

English

SODIUM 5-ETHYL-5-BUTYLBARBITURATE

Systematic Name

English

BUTOBARBITONE SODIUM

Systematic Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-BUTYL-5-ETHYL-, SODIUM SALT (1:1)

Systematic Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-BUTYL-5-ETHYL-, MONOSODIUM SALT

Systematic Name

English

Classification Tree Code System Code

DEA NO.

2100