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Details

Stereochemistry ACHIRAL
Molecular Formula C10H16N2O3
Molecular Weight 212.2456
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTETHAL

SMILES

CCCCC1(CC)C(=O)NC(=O)NC1=O

InChI

InChIKey=STDBAQMTJLUMFW-UHFFFAOYSA-N
InChI=1S/C10H16N2O3/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)

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

Description
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

1923
5
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
186
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Soneryl

Approved Use

Soneryl is indicated for the treatment of insomnia.
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP450
32
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP450
41
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L1MLX
Alsachim
3028
http://www.alsachim.com/product-C4103-glo.bal-view.html
Ambinter
Amb10606518
http://www.ambinter.com/reference/10606518
Chemieliva Pharmaceutical Co., Ltd
PBCM0825944
ChemMol
99151444
http://www.chemmol.com/chemmol/99151444.html
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
mcule
MCULE-8998219052
https://mcule.com/MCULE-8998219052
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
PubMed

PubMed

TitleDatePubMed
The prevalence, incidence and risk factors of herpes simplex virus type 2 infection among pregnant Zimbabwean women followed up nine months after childbirth.
2010-01-12
A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women.
2008-09-27
40 years hard labour.
2008-05
A polymorph of butobarbital with two distinct hydrogen-bonding motifs.
2007-12
The history of barbiturates a century after their clinical introduction.
2005-12
Epidural abscess caused by Streptococcus milleri in a pregnant woman.
2005-11-03
5-Butyl-5-ethylbarbituric acid: a phase transition at low temperature.
2005-05
[A century of barbiturates in neurology].
2004-10-30
Effects of MK-801 (dizocilpine) on brain cell membrane function and energy metabolism in experimental Escherichia coli meningitis in the newborn piglet.
2003-04
[Acute renal failure caused by ajmaline-butobarbital].
1983-06-25
Patents

Patents

DE481129
2
US20090110724
2

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 Mon Mar 31 17:34:21 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:21 GMT 2025
Record UNII
OHZ8QAW6YC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTOBARBITAL
MART.   WHO-DD  
Preferred Name English
BUTETHAL
MI  
Common Name English
NSC-229336
Code English
BUTETHAL [MI]
Common Name English
BUTOBARBITONE
Common Name English
Butobarbital [WHO-DD]
Common Name English
5-BUTYL-5-ETHYLBARBITURIC ACID
Systematic Name English
BUTOBARBITAL [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QN05CA03
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
LIVERTOX 132
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
NCI_THESAURUS C67084
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
DEA NO. 2100
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
WHO-ATC N05CA03
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
Code System Code Type Description
DRUG BANK
DB01353
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
NSC
229336
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
DRUG CENTRAL
449
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
NCI_THESAURUS
C87459
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-019-9
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
MERCK INDEX
m2794
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY Merck Index
PUBCHEM
6473
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
WIKIPEDIA
BUTOBARBITAL
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
RXCUI
19874
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY RxNorm
FDA UNII
OHZ8QAW6YC
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
ChEMBL
CHEMBL404422
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
EVMPD
SUB13135MIG
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID70227808
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
MESH
C027712
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
CAS
77-28-1
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
SMS_ID
100000076905
Created by admin on Mon Mar 31 17:34:21 GMT 2025 , Edited by admin on Mon Mar 31 17:34:21 GMT 2025
PRIMARY
Related Record Type Details
Structure of BUTETHAL SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BUTETHAL
ACTIVE MOIETY
NIH
NCATS
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