BUTABARBITAL

US Previously Marketed

First approved in 1939

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H16N2O3
Molecular Weight	212.2456
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(C)C1(CC)C(=O)NC(=O)NC1=O

InChI

InChIKey=ZRIHAIZYIMGOAB-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/000793s025lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10209232

Barbiturates are non-selective depressants of the central nervous system. Butabarbital is one of them, which is used under brand name butisol sodium as a sedative or hypnotic. Like other barbiturates, butabarbital is capable of producing all levels of CNS mood alteration from excitation to mild sedation, to hypnosis, and deep coma. The mechanism of action by which barbiturates exert their effect is not yet completely understood, but is assumed, that butabarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264449	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sleeplessness 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/000793s025lbl.pdf	Primary		Approved 8429	BUTISOL SODIUM Approved Use BUTISOL SODIUM (butabarbital sodium tablets, USP and butabarbital sodium oral solution, USP) is indicated for use as a sedative or hypnotic. Since barbiturates appear to lose their effectiveness for sleep induction and sleep maintenance after 2 weeks, use of BUTISOL SODIUM in treating insomnia should be limited to this time. Launch Date 1939

Doses

Dose	Population	Adverse events
15 mg 4 times / day multiple, oral Recommended Dose: 15 mg, 4 times / day Route: oral Route: multiple Dose: 15 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4262210/	unhealthy, 36 n = 16 Health Status: unhealthy Condition: low back syndrome Age Group: 36 Sex: M+F Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/4262210/	Disc. AE: Drowsiness... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/4262210/
30 mg 4 times / day multiple, oral Recommended Dose: 30 mg, 4 times / day Route: oral Route: multiple Dose: 30 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/	unhealthy, adult n = 32 Health Status: unhealthy Condition: anxiety Age Group: adult Sex: M+F Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/	Other AEs: Sedation... Other AEs: Sedation (10 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/
30 mg 4 times / day multiple, oral Recommended Dose: 30 mg, 4 times / day Route: oral Route: multiple Dose: 30 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/	unhealthy, adult n = 40 Health Status: unhealthy Condition: anxiety Age Group: adult Sex: M+F Population Size: 40 Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/	Other AEs: Sedation... Other AEs: Sedation (14 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/

AEs

AE	Significance	Dose	Population
Drowsiness	1 patient Disc. AE	15 mg 4 times / day multiple, oral Recommended Dose: 15 mg, 4 times / day Route: oral Route: multiple Dose: 15 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4262210/	unhealthy, 36 n = 16 Health Status: unhealthy Condition: low back syndrome Age Group: 36 Sex: M+F Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/4262210/
Sedation	10 patients	30 mg 4 times / day multiple, oral Recommended Dose: 30 mg, 4 times / day Route: oral Route: multiple Dose: 30 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/	unhealthy, adult n = 32 Health Status: unhealthy Condition: anxiety Age Group: adult Sex: M+F Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/
Sedation	14 patients	30 mg 4 times / day multiple, oral Recommended Dose: 30 mg, 4 times / day Route: oral Route: multiple Dose: 30 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/	unhealthy, adult n = 40 Health Status: unhealthy Condition: anxiety Age Group: adult Sex: M+F Population Size: 40 Sources: https://pubmed.ncbi.nlm.nih.gov/4913869/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inducer 781

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1054

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1925	inducer 1573 Sources: https://www.wellrx.com/butisol%20sodium/monographs/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30443785/ Page: 11.0	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30443785/ Page: 11.0	yes

Sourcing

Vendor/Aggregator	ID	URL
Alsachim	3096	http://www.alsachim.com/product-C4174-glo.bal-view.html
Aurora Fine Chemicals LLC	A17.920.718	http://online.aurorafinechemicals.com/info?ID=A17.920.718
Avantor Inc	75835-278	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
Chem Scene	CS-7224	http://www.chemscene.com/125-40-6.html
ChemMol	30105098	http://www.chemmol.com/chemmol/30105098.html
ChemMol	49415741	http://www.chemmol.com/chemmol/49415741.html
Clearsynth	CS-EB-00333	https://www.clearsynth.com/en/CSEB00333.html
Clearsynth	CS-ER-00325	https://www.clearsynth.com/en/CSER00325.html
MedChem Express	HY-U00167	http://www.medchemexpress.com/NSC27517.html
Sigma-Aldrich	B-024_CERILLIAN	http://www.sigmaaldrich.com/catalog/product/cerillian/b024?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S522301	http://www.smolecule.com/products/s522301
THE BioTek	bt-262147	https://www.thebiotek.com/product/inhibitors/bt-262147

PubMed

Title	Date	PubMed
Comparative abuse liability and pharmacological effects of meprobamate, triazolam, and butabarbital.	2003 Jun	12826989
The history of barbiturates a century after their clinical introduction.	2005 Dec	18568113
Treatment with the xanthine oxidase inhibitor, allopurinol, improves nerve and vascular function in diabetic rats.	2007 Apr 30	17291486
Management of acute diarrhoea in primary care in Bahrain: self-reported practices of doctors.	2007 Jun	17985822
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486

Sample Use Guides

In Vivo Use Guide

Usual adult dosage: daytime sedative - 15 to 30 mg, 3 or 4 times daily. Bedtime hypnotic - 50 to 100 mg. Preoperative sedative - 50 to 100 mg, 60 to 90 minutes before surgery. Usual pediatric dosage: preoperative sedative - 2 to 6 mg/kg maximum 100 mg.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

BUTABARBITAL

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-(1-METHYLPROPYL)-

Systematic Name

English

NILOX

Brand Name

English

BUTABARBITAL [USP MONOGRAPH]

Common Name

English

SECBUTABARBITAL

Official Name

English

SECBUTABARBITAL [MART.]

Common Name

English

BUTABARBITAL [USP IMPURITY]

Common Name

English

BUTABARBITAL [MI]

Common Name

English

BUTATAB

Brand Name

English

5-sec-Butyl-5-ethylbarbituric acid

Systematic Name

English

BUTABARBITAL CIII [USP-RS]

Common Name

English

BARBITURIC ACID, 5-SEC-BUTYL-5-ETHYL-

Systematic Name

English

Secbutabarbital [WHO-DD]

Common Name

English

secbutabarbital [INN]

Common Name

English

SEC-BUTOBARBITONE

Common Name

English

BUTABARBITAL [HSDB]

Common Name

English

BUTABARBITAL CIII

Common Name

English

UNICELLES

Brand Name

English

5-ETHYL-5-(1-METHYLPROPYL)-2,4,6(1H,3H,5H)-PYRIMIDINETRIONE

Systematic Name

English

MEDARSED

Brand Name

English

BUTABARBITAL [VANDF]

Common Name

English

Classification Tree Code System Code

DEA NO.

2100