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

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
The alcoholic metabolites of pentobarbital and amobarbital in man.	1965 Oct	5855308
Dystonic reactions to prochlorperazine in hypoparathyroidism.	1966 Nov 3	5331863
Hypomagnesemia with convulsions in a newborn infant. Report of a case associated with maternal hypophosphatemia.	1967 Sep 30	6069279
Hypotensive effects of chlordiazepoxide, amobarbital and chlorpromazine on behaviorally induced elevated arterial blood pressure in the squirrel monkey.	1970 Jun	4988497
Amobarbital metabolism in man: N-glucoside formation.	1978 Jul	684279
Seven cases of somnambulism induced by drugs.	1979 Jul	453369
Regulation of hepatic nitric oxide synthase by reactive oxygen intermediates and glutathione.	1995 Feb 1	7532384
Clinical experimental observations of carotid artery injections of sodium amytal.	1997 Feb	9056272
Transcortical mixed aphasia due to cerebral infarction in left inferior frontal lobe and temporo-parietal lobe.	2002 Feb	11942365
Evidence that a type-2 NADH:quinone oxidoreductase mediates electron transfer to particulate methane monooxygenase in methylococcus capsulatus.	2002 Feb 1	11811946
Wada testing reveals frontal lateralization for the memorization of words and faces.	2002 Jan 1	11798392
Key structural features of ligands for activation of human pregnane X receptor.	2004 Apr	15039302
Uridine diphosphate sugar-selective conjugation of an aldose reductase inhibitor (AS-3201) by UDP-glucuronosyltransferase 2B subfamily in human liver microsomes.	2004 Apr 1	15013842
Intracarotid Amytal memory test and hippocampal magnetic resonance imaging volumetry: validity of the Wada test as an indicator of hippocampal integrity among candidates for epilepsy surgery.	2004 Dec	15597752
Role of endothelial mitochondria in oxidant production and modulation of neutrophil adherence.	2004 Sep-Oct	15479985
Effects of electron transport inhibitors and uncouplers on the oxidation of ferrous iron and compounds interacting with ferric iron in Acidithiobacillus ferrooxidans.	2005 Aug	16234867
Contribution of the PI 3-kinase/Akt survival pathway toward osmotic preconditioning.	2005 Jan	15786717
P2Y2 nucleotide receptor up-regulation in submandibular gland cells from the NOD.B10 mouse model of Sjögren's syndrome.	2005 Jun	15848146
Amygdalohippocampal involvement in tinnitus and auditory memory.	2006 Dec	17114143
Ecto-5'-nucleotidase: Structure function relationships.	2006 Jun	18404474
Analysis of donors of electrons to photosystem I and cyclic electron flow by redox kinetics of P700 in chloroplasts of isolated bundle sheath strands of maize.	2007 Apr	17551845
Neuroprotective role of neurophysiological monitoring during endovascular procedures in the brain and spinal cord.	2007 Dec	18083497
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007 Jan	17003167
Stimulation-induced changes in NADH fluorescence and mitochondrial membrane potential in lizard motor nerve terminals.	2007 Mar 15	17218351
[Applications of optical topography in neurosurgery].	2007 May	17533971
Preoperative cellulose porous beads for therapeutic embolization of meningioma: provocation test and technical considerations.	2007 May	17318600
Identification of a novel topoisomerase inhibitor effective in cells overexpressing drug efflux transporters.	2009 Oct 2	19798419
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Transitional Nerve: A New and Original Classification of a Peripheral Nerve Supported by the Nature of the Accessory Nerve (CN XI).	2010	21318044
Mutism as the presenting symptom: three case reports and selective review of literature.	2010 Jan	21799563
Multiple myeloma presenting as CEA-producing rectal cancer.	2010 Mar 31	21139949
Prozone effect of serum IgE levels in a case of plasma cell leukemia.	2010 Sep 10	20828419
[The use of enzymatic hydrolysis for isolation of barbituric acid derivatives from blood (as exemplified by phenobarbital and barbamyl)].	2010 Sep-Oct	21265178

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.

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