Butabarbital

Butabarbital

Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682417
ATC code	none
Legal status
Legal status	CA: Schedule IV DE: Anlage II (Prohibited) US: Schedule III
Pharmacokinetic data
Biological half-life	100 hours.
Excretion	Urine
Identifiers
IUPAC name 5-butan-2-yl-5-ethyl-1,3-diazinane-2,4,6-trione
Synonyms	Butabarbital, Butisol
CAS Number	125-40-6 Y
PubChem (CID)	2479
IUPHAR/BPS	7137
DrugBank	DB00237 Y
ChemSpider	2385 Y
UNII	P0078O25A9 Y
KEGG	D03180 Y
ChEBI	CHEBI:3228 Y
ChEMBL	CHEMBL449 Y
ECHA InfoCard	100.004.308
Chemical and physical data
Formula	C10H16N2O3
Molar mass	212.246 g/mol
3D model (Jmol)	Interactive image
SMILES O=C1NC(=O)NC(=O)C1(C(C)CC)CC
InChI InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15) Y Key:ZRIHAIZYIMGOAB-UHFFFAOYSA-N Y

Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. 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 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.

(R)-Stereoisomer

(S)-Stereoisomer

Butabarbital is also sold in combination with belladonna alkaloids under the brand name Butibel. The belladonna is added for antispasmodic effect. This product contains a low dose of butabarbital combined with a standardised mix of belladonna alkaloids and is used as an antispasmodic taken to relieve cramping and spasms of the stomach and intestines. They are used also to decrease the amount of acid formed in the stomach. Another similar product is Donnatal, which contains belladonna alkaloids combined with phenobarbital.

Barbiturates were first discovered to have medical use in 1903, when a research at Bayer showed barbital to be an effective sedative for dogs. It was not until the mid 20th century that the habit forming nature of barbiturates and behavioral side effects were first noted

Butabarbital was approved for medical use in 2007 under the brand name Butisol Sodium. Butisol sodium is manufactured by Meda Pharmaceuticals as a Schedule III controlled substance due to its high risk for abuse and dependence. Benzodiazapines are more commonly administered today for their similar sedative and hypnotic properties, and reduced risk of physical dependence. Barbiturate drugs such as butabarbital sodium are used now for short-term and acute treatment under strict doctor supervision only

Barbiturates are non-selective depressants of the central nervous system, inducing drowsiness and mild sedative effects. Barbiturate hypnotics are used in the treatment of sleep and anxiety disorders for their calming and sedative properties, however are usually restricted to short term use due to risk of dependency.