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Details

Stereochemistry RACEMIC
Molecular Formula C12H17N2O3.Na
Molecular Weight 260.2647
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SECOBARBITAL SODIUM

SMILES

[Na+].CCCC(C)C1(CC=C)C(=O)NC(=O)[N-]C1=O

InChI

InChIKey=AXXJTNXVUHVOJW-UHFFFAOYSA-M
InChI=1S/C12H18N2O3.Na/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);/q;+1/p-1

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
Seven cases of somnambulism induced by drugs.
1979 Jul
Reflex sympathetic dystrophy associated with antiepileptic drugs.
1994 Mar-Apr
Dog liver microsomal P450 enzyme-mediated toluene biotransformation.
1995 Nov
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 SODIUM
GREEN BOOK   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
QUINALBARBITONE SODIUM
Common Name English
SECOBARBITAL SODIUM [VANDF]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-(1-METHYLBUTYL)-5-(2-PROPENYL)-, MONOSODIUM SALT
Common Name English
SEBAR
Brand Name English
SECOBARBITAL SODIUM [USP IMPURITY]
Common Name English
BARBOSEC
Brand Name English
SECOBARBITAL SODIUM [USP MONOGRAPH]
Common Name English
SECOBARBITAL SODIUM [MART.]
Common Name English
SECOBARBITAL SODIUM [JAN]
Common Name English
EVRONAL SODIUM
Brand Name English
PRAMIL
Brand Name English
IMMENOCTAL
Brand Name English
SECOBARBITAL SODIUM [GREEN BOOK]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-(1-METHYLBUTYL)-5-(2-PROPEN-1-YL)-, SODIUM SALT (1:1)
Systematic Name English
SECOBARBITAL SODIUM [MI]
Common Name English
Secobarbital sodium [WHO-DD]
Common Name English
SYNATE
Brand Name English
(RS)-SECOBARBITAL SODIUM
Common Name English
NSC-10818
Code English
5-ALLYL-5-(1-METHYLBUTYL)BARBITURIC ACID SODIUM SALT
Common Name English
SECOBARBITAL SODIUM [ORANGE BOOK]
Common Name English
BARBITURIC ACID, 5-ALLYL-5-(1-METHYLBUTYL)-, SODIUM SALT
Common Name English
Classification Tree Code System Code
DEA NO. 2315
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
CFR 21 CFR 522.900
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
Code System Code Type Description
CAS
51165-35-6
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
SUPERSEDED
DAILYMED
XBP604F6UM
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
NCI_THESAURUS
C66530
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
PUBCHEM
14148199
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
MERCK INDEX
m9827
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY Merck Index
FDA UNII
XBP604F6UM
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022019
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
ChEMBL
CHEMBL447
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
NSC
10818
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
CAS
4847-61-4
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
SUPERSEDED
ECHA (EC/EINECS)
206-218-4
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
SMS_ID
100000084947
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
EVMPD
SUB04344MIG
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
RXCUI
91110
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY RxNorm
DRUG BANK
DBSALT000255
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY
CAS
309-43-3
Created by admin on Fri Dec 15 16:32:07 GMT 2023 , Edited by admin on Fri Dec 15 16:32:07 GMT 2023
PRIMARY