U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BUTABARBITAL

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

Doses

DosePopulationAdverse 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:
unhealthy, 36
n = 16
Health Status: unhealthy
Condition: low back syndrome
Age Group: 36
Sex: M+F
Population Size: 16
Sources:
Disc. AE: Drowsiness...
AEs leading to
discontinuation/dose reduction:
Drowsiness (1 patient)
Sources:
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:
unhealthy, adult
n = 32
Health Status: unhealthy
Condition: anxiety
Age Group: adult
Sex: M+F
Population Size: 32
Sources:
Other AEs: Sedation...
Other AEs:
Sedation (10 patients)
Sources:
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:
unhealthy, adult
n = 40
Health Status: unhealthy
Condition: anxiety
Age Group: adult
Sex: M+F
Population Size: 40
Sources:
Other AEs: Sedation...
Other AEs:
Sedation (14 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 36
n = 16
Health Status: unhealthy
Condition: low back syndrome
Age Group: 36
Sex: M+F
Population Size: 16
Sources:
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:
unhealthy, adult
n = 32
Health Status: unhealthy
Condition: anxiety
Age Group: adult
Sex: M+F
Population Size: 32
Sources:
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:
unhealthy, adult
n = 40
Health Status: unhealthy
Condition: anxiety
Age Group: adult
Sex: M+F
Population Size: 40
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
The history of barbiturates a century after their clinical introduction.
2005 Dec
Treatment with the xanthine oxidase inhibitor, allopurinol, improves nerve and vascular function in diabetic rats.
2007 Apr 30
Management of acute diarrhoea in primary care in Bahrain: self-reported practices of doctors.
2007 Jun
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010

Sample Use Guides

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
HSDB   MI   USP   VANDF  
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
INN   MART.   WHO-DD  
INN  
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
USP-RS  
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
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
204-738-6
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
NCI_THESAURUS
C61657
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
MESH
C084833
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
CAS
125-40-6
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL449
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
CAS
97164-73-3
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
SUPERSEDED
RS_ITEM_NUM
1079000
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
HSDB
3018
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
WIKIPEDIA
BUTABARBITAL
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
LACTMED
Butabarbital
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
DRUG CENTRAL
439
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
SMS_ID
100000085806
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
FDA UNII
P0078O25A9
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
PUBCHEM
2479
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
INN
1152
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
DRUG BANK
DB00237
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022709
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
RXCUI
477631
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m2779
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY Merck Index
IUPHAR
7137
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
CHEBI
3228
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY
EVMPD
SUB10465MIG
Created by admin on Fri Dec 15 17:23:02 GMT 2023 , Edited by admin on Fri Dec 15 17:23:02 GMT 2023
PRIMARY