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

Details

Stereochemistry RACEMIC
Molecular Formula C12H18N2O3
Molecular Weight 238.2829
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SECOBARBITAL

SMILES

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

InChI

InChIKey=KQPKPCNLIDLUMF-UHFFFAOYSA-N
InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/seconal-sodium-drug.htm http://www.wikidoc.org/index.php/Secobarbital_sodium https://www.glowm.com/resources/glowm/cd/pages/drugs/s004.html

Secobarbital sodium, a barbiturate, is FDA approved for the treatment of insomnia and for pre-anesthetic use. This drug binds at a distinct 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. Adverse reactions are drowsiness, lethargy, hangover, paradoxical excitement in elderly patients, somnolence. Rifampin may decrease secobarbital levels by increasing metabolism.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SECONAL SODIUM

Approved Use

A.Hypnotic, for the short-term treatment of insomnia, since it appears to lose its effectiveness for sleep induction and sleep maintenance after 2 weeks (see Clinical Pharmacology). B.Preanesthetic

Launch Date

1983
Preventing
SECONAL SODIUM

Approved Use

A.Hypnotic, for the short-term treatment of insomnia, since it appears to lose its effectiveness for sleep induction and sleep maintenance after 2 weeks (see Clinical Pharmacology). B.Preanesthetic

Launch Date

1983
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2 μg/mL
5 mg/kg single, rectal
dose: 5 mg/kg
route of administration: Rectal
experiment type: SINGLE
co-administered:
SECOBARBITAL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
20.2 μg × h/mL
5 mg/kg single, rectal
dose: 5 mg/kg
route of administration: Rectal
experiment type: SINGLE
co-administered:
SECOBARBITAL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.9 h
5 mg/kg single, rectal
dose: 5 mg/kg
route of administration: Rectal
experiment type: SINGLE
co-administered:
SECOBARBITAL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
16.5 mg single, intraarterial (mean)
Recommended
Dose: 16.5 mg
Route: intraarterial
Route: single
Dose: 16.5 mg
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: neurological disorders
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Other AEs: Scintillating scotoma, Epileptic fit...
Other AEs:
Scintillating scotoma (1 patient)
Epileptic fit (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Epileptic fit 1 patient
16.5 mg single, intraarterial (mean)
Recommended
Dose: 16.5 mg
Route: intraarterial
Route: single
Dose: 16.5 mg
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: neurological disorders
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Scintillating scotoma 1 patient
16.5 mg single, intraarterial (mean)
Recommended
Dose: 16.5 mg
Route: intraarterial
Route: single
Dose: 16.5 mg
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: neurological disorders
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
A hypotensive episode caused by amitriptyline?
1969 Oct 4
Volkmann's ischemic contracture after intra-arterial injection of secobarbital.
1970 Apr 20
Pharmacological comparison of R(+), S(-) and racemic secobarbital in mice.
1970 Mar
Toxic nephropathy after low-dose methoxyflurane anesthesia: drug interaction with secobarbital?
1976 Feb 21
Seven cases of somnambulism induced by drugs.
1979 Jul
Differential regulation of gamma-aminobutyric acid receptor channels by diazepam and phenobarbital.
1989 Mar
Reflex sympathetic dystrophy associated with antiepileptic drugs.
1994 Mar-Apr
Dog liver microsomal P450 enzyme-mediated toluene biotransformation.
1995 Nov
[Experience in managing refractory status epilepticus caused by viral encephalitis under long-term anesthesia with barbiturate: a case report].
1998 May
Induction of CYP1A2 by phenobarbital in the livers of aryl hydrocarbon-responsive and -nonresponsive mice.
1999 Mar
Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1.
2004 Dec
Physician-assisted suicide: a review of the literature concerning practical and clinical implications for UK doctors.
2006 Jun 22
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection.
2009 Jun
Identification and validation of novel human pregnane X receptor activators among prescribed drugs via ligand-based virtual screening.
2011 Feb
Patents

Sample Use Guides

As a hypnotic, 100 mg at bedtime. Preoperatively, 200 to 300 mg 1 to 2 hours before surgery.
Route of Administration: Other
In Vitro Use Guide
Early studies revealed that 0.2 mM secobarbital caused a maximum decrease in cytochrome P450, requiring NADPH or an NADPH-generating system.
Name Type Language
SECOBARBITAL
HSDB   INN   MART.   USP   VANDF   WHO-DD  
INN  
Official Name English
SECOBARBITAL [HSDB]
Common Name English
SECOBARBITONE
Common Name English
SECOBARBITAL [VANDF]
Common Name English
MEBALLYMAL
Brand Name English
SECOBARBITAL [MART.]
Common Name English
QUINALBARBITAL
Brand Name English
SECOBARBITAL SODIUM FREE ACID [MI]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-(1-METHYLBUTYL)-5-(2-PROPENYL)-
Systematic Name English
(±)-QUINALBARBITONE
Common Name English
(RS)-SECOBARBITAL
Common Name English
BARBITURIC ACID, 5-ALLYL-5-(1-METHYLBUTYL)-
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-(1-METHYLBUTYL)-5-(2-PROPEN-1-YL)-
Systematic Name English
EVRONAL
Brand Name English
SOMATARAX
Brand Name English
IMMENOX
Brand Name English
5-(1-METHYLBUTYL)-5-(2-PROPEN-1-YL)-2,4,6(1H,3H,5H)-PYRIMIDINETRIONE
Systematic Name English
SECONAL
Brand Name English
SECOBARBITAL CII
Common Name English
HYPOTROL
Brand Name English
SECOBARBITAL [USP IMPURITY]
Common Name English
Secobarbital [WHO-DD]
Common Name English
SECOBARBITAL [USP-RS]
Common Name English
secobarbital [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC N05CA06
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
WHO-VATC QN05CA06
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
LIVERTOX 876
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
WHO-VATC QN51AA02
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
WHO-VATC QN51AA52
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
DEA NO. 2315
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
NCI_THESAURUS C67084
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
Code System Code Type Description
CAS
76-73-3
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
NCI_THESAURUS
C61937
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
EVMPD
SUB10468MIG
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
PUBCHEM
5193
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
INN
146
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
DRUG CENTRAL
2428
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
DRUG BANK
DB00418
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
WIKIPEDIA
SECOBARBITAL
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
CAS
29071-21-4
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
SUPERSEDED
DAILYMED
1P7H87IN75
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-982-2
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
HSDB
3182
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
LACTMED
Secobarbital
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
RXCUI
9624
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY RxNorm
IUPHAR
7615
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
RS_ITEM_NUM
1611004
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
SMS_ID
100000084104
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
MERCK INDEX
m9827
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
FDA UNII
1P7H87IN75
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID6044145
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
CHEBI
9073
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
MESH
D012631
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL447
Created by admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
PRIMARY