SECOBARBITAL

US Previously Marketed

First marketed in 1929

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H18N2O3
Molecular Weight	238.2834
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(C)C1(CC=C)C(=NC(=O)N=C1O)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

Molecular Formula	C12H18N2O3
Molecular Weight	238.2834
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 189 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 157

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 100 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d892a312-12ba-4d32-a840-2c0ff3dc1d58	Primary		Approved 8043	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 4.33987191E11
Preoperative sedation 2 Sources: https://www.glowm.com/resources/glowm/cd/pages/drugs/s004.html	Preventing		Approved 8043	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 4.16102416E11

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 355

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A2 637 CYP2C19 269

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1532	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/10064569/	yes
CYP2C19 1392	inducer 1440 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 1648	inducer 1440 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
[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

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.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 09:28:24 UTC 2021` Edited by `admin` on `Sat Jun 26 09:28:24 UTC 2021`
Record UNII	1P7H87IN75
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SECOBARBITAL

Official Name

English

SECOBARBITAL [HSDB]

Common Name

English

SECOBARBITAL [USP]

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-RS]

Common Name

English

SECOBARBITAL [WHO-DD]

Common Name

English

SECOBARBITAL [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05CA06