Skip to content
Vinony
English
EnglishBahasa IndonesiaDeutschEspañolNederlandsPolskiPortuguêsTiếng Việtالعربيةفارسی
butabarbital

Structure via PubChem · Public domain (PubChem)

EntityQ410608· pop 15· linked from 602 articles

butabarbital

Sign in to save

Also known as Butisol®, 5-sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)barbituric acid, 5-sec-butyl-5-ethylbarbituric acid, secbutabarbital, Butisol, 5-sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione

Butabarbital (brand name Butisol) is a prescription barbiturate sleep aid and anxiety medication. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia, relieving general anxiety and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its intermediate duration of action

Key facts

Drug.verifiedrevid
443491373
Drug.IUPAC_name
5-butan-2-yl-5-ethyl-1,3-diazinane-2,4,6-trione
Drug.image
Butabarbital.svg
Drug.image_class
skin-invert-image
Drug.width
120
Drug.tradename
Butisol
Drug.MedlinePlus
a682417
Drug.DailyMedID
Butabarbital
Drug.legal_BR
B1
Drug.legal_CA
Schedule IV
Drug.legal_US
Schedule III
Drug.legal_DE
Anlage II
Drug.elimination_half life
100 hours
Drug.excretion
Urine
Drug.IUPHAR_ligand
7137 <!--
Drug.CASNo_Ref
-->
Drug.CAS_number
125-40-6
Drug.ATC_prefix
none

via Wikipedia infobox

Chemical data

Formula
C10H16N2O3
Molecular weight
212.25 g/mol
IUPAC name
5-butan-2-yl-5-ethyl-1,3-diazinane-2,4,6-trione
SMILES
CCC(C)C1(C(=O)NC(=O)NC1=O)CC
InChIKey
ZRIHAIZYIMGOAB-UHFFFAOYSA-N
XLogP
1.6
Polar surface area
75.3 Ų
H-bond donors
2
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
1939
Admin. routes
oral

via ChEMBL · EBI

Research

62 papers

via PubMed

Wikidata facts

Subclass of
chemical compound
Mass
212.116092
Has use
medication
Show 6 more facts
chemical formula
C₁₀H₁₆N₂O₃
medical condition treated
insomnia
canonical SMILES
CCC(C)C1(C(=O)NC(=O)NC1=O)CC
Commons category
Butabarbital
different from
butethal
World Health Organisation international non-proprietary name
secbutabarbitalum
Sources (3)

via Wikidata · CC0

~6 min read

Encyclopedic overview

13 sections
Contents
  • History
  • Clinical uses
  • Administration
  • Clinical effects & elimination
  • Overdose & abuse
  • Side effects
  • Adverse effects
  • Contradictions
  • Pharmacology
  • Absorption, distribution and excretion
  • Mechanism of action
  • References
  • External links

Butabarbital (brand name Butisol) is a prescription barbiturate sleep aid and anxiety medication. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia, relieving general anxiety and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its intermediate duration of action gives butabarbital an abuse potential slightly lower than secobarbital. Butabarbital can be hydrolyzed to valnoctamide.

{| class="wikitable" style="text-align:center" |+ Stereoisomeres of butabarbital |- | class=skin-invert-image|120px || class=skin-invert-image|120px |- | (R)-Stereoisomer || (S)-Stereoisomer |}

Excerpted from Wikipedia’s “butabarbital” article, available under the CC BY-SA 4.0 licence.

Gallery (3)

Available in 14 languages

via Wikidata sitelinks · CC0