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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

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SECONAL SODIUM
Preventing
SECONAL SODIUM

Cmax

ValueDoseCo-administeredAnalytePopulation
2 μg/mL
5 mg/kg single, rectal
SECOBARBITAL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
20.2 μg × h/mL
5 mg/kg single, rectal
SECOBARBITAL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.9 h
5 mg/kg single, rectal
SECOBARBITAL plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
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.