SECOBARBITAL

US Previously Marketed

First marketed in 1929

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 Search

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
Sources: https://www.drugs.com/cdi/secobarbital.html
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.

CNS Activity

Originator

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/2850060 \| https://www.ncbi.nlm.nih.gov/pubmed/6331574 \| https://www.ncbi.nlm.nih.gov/pubmed/3006661	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d892a312-12ba-4d32-a840-2c0ff3dc1d58	Primary		Approved 8429	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
Preoperative sedation 2 Sources: https://www.glowm.com/resources/glowm/cd/pages/drugs/s004.html	Preventing		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175723/	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

Value	Dose	Co-administered	Analyte	Population
20.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175723/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175723/	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

Dose	Population	Adverse events
16.5 mg single, intraarterial (mean) Recommended Dose: 16.5 mg Route: intraarterial Route: single Dose: 16.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/	unhealthy, adult n = 43 Health Status: unhealthy Condition: neurological disorders Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/	Other AEs: Scintillating scotoma, Epileptic fit... Other AEs: Scintillating scotoma (1 patient) Epileptic fit (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/

AEs

AE	Significance	Dose	Population
Epileptic fit	1 patient	16.5 mg single, intraarterial (mean) Recommended Dose: 16.5 mg Route: intraarterial Route: single Dose: 16.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/	unhealthy, adult n = 43 Health Status: unhealthy Condition: neurological disorders Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/
Scintillating scotoma	1 patient	16.5 mg single, intraarterial (mean) Recommended Dose: 16.5 mg Route: intraarterial Route: single Dose: 16.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/	unhealthy, adult n = 43 Health Status: unhealthy Condition: neurological disorders Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/20854063/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inducer 389

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A2 701 CYP2C19 293

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/10064569/	yes
CYP2C19 1553	inducer 1573 Sources: /web/20210202195346/http://portals.clevelandclinic.org/portals/66/pdf/technical-briefs/genetic-test-of-cytochrome-p450-2c19-cyp2c19-for-drug-metabolism.pdf	yes
CYP2C9 1819	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/17558303/ Page: 3.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AN PharmaTech	AN-23386
ChemMol	49416172	http://www.chemmol.com/chemmol/49416172.html
NovoSeek	14148199
PubChem	14148199	https://pubchem.ncbi.nlm.nih.gov/compound/14148199
Smolecule	S542905	http://www.smolecule.com/products/s542905
THE BioTek	bt-282493	https://www.thebiotek.com/product/inhibitors/bt-282493

PubMed

Title	Date	PubMed
A hypotensive episode caused by amitriptyline?	1969 Oct 4	4186181
Volkmann's ischemic contracture after intra-arterial injection of secobarbital.	1970 Apr 20	5467300
Pharmacological comparison of R(+), S(-) and racemic secobarbital in mice.	1970 Mar	5440306
Toxic nephropathy after low-dose methoxyflurane anesthesia: drug interaction with secobarbital?	1976 Feb 21	1253070
Seven cases of somnambulism induced by drugs.	1979 Jul	453369
Differential regulation of gamma-aminobutyric acid receptor channels by diazepam and phenobarbital.	1989 Mar	2471436
Reflex sympathetic dystrophy associated with antiepileptic drugs.	1994 Mar-Apr	8156963
Dog liver microsomal P450 enzyme-mediated toluene biotransformation.	1995 Nov	8592870
[Experience in managing refractory status epilepticus caused by viral encephalitis under long-term anesthesia with barbiturate: a case report].	1998 May	9806000
Induction of CYP1A2 by phenobarbital in the livers of aryl hydrocarbon-responsive and -nonresponsive mice.	1999 Mar	10064569
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	15263067
Physician-assisted suicide: a review of the literature concerning practical and clinical implications for UK doctors.	2006 Jun 22	16792812
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection.	2009 Jun	19299527
Identification and validation of novel human pregnane X receptor activators among prescribed drugs via ligand-based virtual screening.	2011 Feb	21068194

Patents

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.

Name

Type

Language

SECOBARBITAL

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