AMOBARBITAL

US Previously Marketed

First marketed in 1923

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H18N2O3
Molecular Weight	226.2722
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(CCC(C)C)C(=O)NC(=O)NC1=O

InChI

InChIKey=VIROVYVQCGLCII-UHFFFAOYSA-N

InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)

HIDE SMILES / InChI

Molecular Formula	C11H18N2O3
Molecular Weight	226.2722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/ppa/amobarbital-sodium.html

AMOBARBITAL is a barbiturate derivative with hypnotic and sedative properties. In an in vitro study in rat thalamic slices amobarbital worked by activating GABAA receptors, which decreased input resistance, depressed burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increased both the amplitude and decay time of inhibitory postsynaptic currents. Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6099281	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.drugs.com/ppa/amobarbital-sodium.html	Primary		Approved 8429	Amytal Sodium Approved Use Unknown
Insomnia 108 Sources: https://www.drugs.com/ppa/amobarbital-sodium.html	Primary		Approved 8429	Amytal Sodium Approved Use Unknown

PubMed

Title	Date	PubMed
Seven cases of somnambulism induced by drugs.	1979 Jul	453369
The central nervous effects of Mitragyna africanus (Willd) stembark extract in rats.	2001 Oct	11535357
Mitochondrial respiratory chain as a new target for anti-ischemic molecules.	2002 Apr 19	12007918
Transcortical mixed aphasia due to cerebral infarction in left inferior frontal lobe and temporo-parietal lobe.	2002 Feb	11942365
Effect of the new matrix metalloproteinase inhibitor RO-28-2653 on mitochondrial function.	2002 Feb 15	11992641
Wada testing reveals frontal lateralization for the memorization of words and faces.	2002 Jan 1	11798392
Amobarbital inhibits K(+)-stimulated glucose oxidation in cerebellar granule neurons by two mechanisms.	2002 Jun 20	12098585
Key structural features of ligands for activation of human pregnane X receptor.	2004 Apr	15039302
Neurophysiologic monitoring and pharmacologic provocative testing for embolization of spinal cord arteriovenous malformations.	2004 Aug	15313696
Endovascular management of dolichoectasia of the posterior cerebral artery report.	2004 Nov-Dec	15569748
Selective GABA-receptor actions of amobarbital on thalamic neurons.	2004 Oct	15381635
Evaluation of the prophylactic use of mitomycin-C to inhibit haze formation after photorefractive keratectomy in high myopia: a prospective clinical study.	2004 Sep 14	15363107
[Rotenone-insensitive NADH oxydation in mitochondrial suspension occurs by NADH dehydrogenase of respiratory chain fragments].	2004 Sep-Oct	15526465
Role of endothelial mitochondria in oxidant production and modulation of neutrophil adherence.	2004 Sep-Oct	15479985
Amytal interview using intravenous lorazepam in a patient with dissociative fugue.	2006 Nov-Dec	17088173
Different states of energy metabolism in the vertebrate retina can be identified by stimulus-related changes in near UV transmission.	2007 Apr	16902788
Comorbid substance-use in schizophrenia: the file drawer effect, In reply to: Talamo et al., 2006. "Comorbid substance-use in schizophrenia: relation to positive and negative symptoms".	2007 Feb	17055705
Seizures during intracarotid methohexital and amobarbital testing.	2007 Feb	17049312
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007 Jan	17003167
[Applications of optical topography in neurosurgery].	2007 May	17533971
Perioperative modulating factors on astigmatism in sutured cataract surgery.	2009 Dec	20046682
Acquired and congenital disorders of sung performance: A review.	2009 Nov 12	20523851
Multiple myeloma presenting as CEA-producing rectal cancer.	2010 Mar 31	21139949
Identification of a novel phosphorylation site in hepatitis C virus NS5A.	2010 Oct	20592109

Patents

Sample Use Guides

In Vivo Use Guide

Sedative: 30 to 50 mg given 2 or 3 times daily. Hypnotic: 65 to 200 mg at bedtime.

Route of Administration: Oral

In Vitro Use Guide

To 100mkl of the tissue homogenate were added 50 mkl of [3SS]TBPS (at the appropriate concentration, and made in 1 M NaBr), 50 mkl of 50 mM Tris Citrate buffer (to define total binding) or AMOBARBITAL at 100mkM or 50mkl of 40mkM picrotoxinin (to define nonspecific binding). The mixture was incubated 90 min at 21°C and then filtered over glass-fiber filters (Schleicher and Schuell No. 32). Filters were washed three times with 5 ml 0.9% (w:v) NaC1 equilibrated to 21°C and then counted by liquid scintillation spectrometry.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:04 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:04 GMT 2023`
Record UNII	GWH6IJ239E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMOBARBITAL

Official Name

English

amobarbital [INN]

Common Name

English

ISOMYTAL

Brand Name

English

AMOBARBITAL [VANDF]

Common Name

English

AMOBARBITAL [MART.]

Common Name

English

AMOBARBITAL [JAN]

Common Name

English

AMOBARBITAL CII [USP-RS]

Common Name

English

5-Ethyl-5-isopentylbarbituric acid

Systematic Name

English

Amobarbital [WHO-DD]

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-(3-METHYLBUTYL)-

Systematic Name

English

AMOBARBITAL [EP IMPURITY]

Common Name

English

NSC-10815

Code

English

AMOBARBITAL CII

Common Name

English

AMYTAL

Brand Name

English

AMOBARBITAL [HSDB]

Common Name

English

AMOBARBITAL [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05CA02