NAV

Amobarbital

Identification

Summary

Amobarbital is a barbiturate derivative used for the induction of sedation during procedures, short-term management of insomnia, and acute management of refractory tonic-clonic seizures.

Generic Name
Amobarbital
DrugBank Accession Number
DB01351
Background

A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565)

Type
Small Molecule
Groups
Approved, Illicit
Structure
3D
Similar Structures
Weight
Average: 226.2722
Monoisotopic: 226.131742452
Chemical Formula
C11H18N2O3
Synonyms
  • 5-ethyl-5-(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
  • 5-ethyl-5-(3-methylbutyl)barbituric acid
  • 5-ethyl-5-isoamylbarbituric acid
  • 5-ethyl-5-isopentylbarbituric acid
  • Amobarbital
  • Amobarbitale
  • Amylobarbitone
  • Barbamil
  • Barbamyl

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Amobarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses 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 increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Amobarbital also appears to bind neuronal nicotinic acetylcholine receptors.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-2
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-3
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-4
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-5
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-6
potentiator
Humans
UNeuronal acetylcholine receptor subunit alpha-4
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
UGlutamate receptor 2
antagonist
Humans
UGlutamate receptor ionotropic, kainate 2
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Amobarbital is combined with 1,2-Benzodiazepine.
AbaloparatideAmobarbital may increase the hypotensive activities of Abaloparatide.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Amobarbital.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Amobarbital.
AcebutololAmobarbital may increase the hypotensive activities of Acebutolol.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Amobarbital.
AcetaminophenThe metabolism of Acetaminophen can be increased when combined with Amobarbital.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Amobarbital.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Amobarbital.
AclidiniumThe risk or severity of adverse effects can be increased when Amobarbital is combined with Aclidinium.
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Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase the CNS depressant effects of amobarbital.
  • Take on an empty stomach. Taking oral amobarbital sodium on an empty stomach increases the rate of absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Amobarbital sodiumG0313KNC7D64-43-7BNHGKKNINBGEQL-UHFFFAOYSA-M
International/Other Brands
Amytal / Isomytal
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Amytal SodiumInjection, powder, lyophilized, for solution0.5 g/5mLIntramuscular; IntravenousMarathon Pharmaceuticals2008-09-252016-03-31US flag
Amytal SodiumInjection, powder, lyophilized, for solution0.5 g/5mLIntramuscular; IntravenousBausch Health US, LLC2008-09-25Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Tuinal Pulvule 303Amobarbital sodium (50 mg) + Secobarbital sodium (50 mg)CapsuleOralPharmascience Inc1945-12-312004-03-05Canada flag
Tuinal Pulvule 304Amobarbital sodium (100 mg / cap) + Secobarbital sodium (100 mg / cap)CapsuleOralPharmascience Inc1945-12-312004-03-05Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Amytal SodiumAmobarbital sodium (0.5 g/5mL)Injection, powder, lyophilized, for solutionIntramuscular; IntravenousMarathon Pharmaceuticals2008-09-252016-03-31US flag
Amytal SodiumAmobarbital sodium (0.5 g/5mL)Injection, powder, lyophilized, for solutionIntramuscular; IntravenousBausch Health US, LLC2008-09-25Not applicableUS flag

Categories

ATC Codes
N05CA02 — AmobarbitalN05CB01 — Combinations of barbiturates
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Hydropyrimidines / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
2,5-dihydropyrimidine / Aliphatic heteromonocyclic compound / Azacycle / Carbonic acid derivative / Carbonyl group / Hydrocarbon derivative / Hydropyrimidine / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
barbiturates (CHEBI:2673)
Affected organisms
Not Available

Chemical Identifiers

UNII
GWH6IJ239E
CAS number
57-43-2
InChI Key
VIROVYVQCGLCII-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione
SMILES
CCC1(CCC(C)C)C(=O)NC(=O)NC1=O

References

General References
  1. Kim HS, Wan X, Mathers DA, Puil E: Selective GABA-receptor actions of amobarbital on thalamic neurons. Br J Pharmacol. 2004 Oct;143(4):485-94. Epub 2004 Sep 20. [Article]
  2. Maynert EW: The alcoholic metabolites of pentobarbital and amobarbital in man. J Pharmacol Exp Ther. 1965 Oct;150(1):118-21. [Article]
  3. Tang BK, Kalow W, Grey AA: Amobarbital metabolism in man: N-glucoside formation. Res Commun Chem Pathol Pharmacol. 1978 Jul;21(1):45-53. [Article]
  4. Soine PJ, Soine WH: High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine. J Chromatogr. 1987 Nov 27;422:309-14. [Article]
  5. McCall WV: The addition of intravenous caffeine during an amobarbital interview. J Psychiatry Neurosci. 1992 Nov;17(5):195-7. [Article]
Human Metabolome Database
HMDB0015440
KEGG Drug
D00555
KEGG Compound
C07536
PubChem Compound
2164
PubChem Substance
46508165
ChemSpider
2079
RxNav
719
ChEBI
2673
ChEMBL
CHEMBL267894
ZINC
ZINC000004811698
Therapeutic Targets Database
DAP000686
PharmGKB
PA448401
Wikipedia
Amobarbital

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentOsteoarthritis (OA) / Posttraumatic Osteoarthritis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • AAIPharma Inc.
  • Marathon Pharmaceuticals
  • Ranbaxy Laboratories
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous0.5 g/5mL
Powder, for solutionIntramuscular; Intravenous500 mg / amp
CapsuleOral60 mg / cap
CapsuleOral200 mg / cap
CapsuleOral
Prices
Unit descriptionCostUnit
Amytal sodium 0.5 gram vial117.35USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)157 °CPhysProp
water solubility603 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.07HANSCH,C ET AL. (1995)
logS-2.57ADME Research, USCD
pKa7.84SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.897 mg/mLALOGPS
logP1.87ALOGPS
logP1.89Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.48Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.27 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity58 m3·mol-1Chemaxon
Polarizability23.45 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9254
Blood Brain Barrier+0.949
Caco-2 permeable-0.5913
P-glycoprotein substrateSubstrate0.6471
P-glycoprotein inhibitor INon-inhibitor0.5906
P-glycoprotein inhibitor IINon-inhibitor0.9426
Renal organic cation transporterNon-inhibitor0.9307
CYP450 2C9 substrateNon-substrate0.7591
CYP450 2D6 substrateNon-substrate0.9011
CYP450 3A4 substrateNon-substrate0.663
CYP450 1A2 substrateNon-inhibitor0.879
CYP450 2C9 inhibitorNon-inhibitor0.7603
CYP450 2D6 inhibitorNon-inhibitor0.9299
CYP450 2C19 inhibitorNon-inhibitor0.7269
CYP450 3A4 inhibitorNon-inhibitor0.9422
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9105
Ames testNon AMES toxic0.691
CarcinogenicityNon-carcinogens0.8925
BiodegradationNot ready biodegradable0.944
Rat acute toxicity2.9884 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9852
hERG inhibition (predictor II)Non-inhibitor0.8963
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.4 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - CI-BGC-MSsplash10-004i-0090000000-5962005393da49f25b6d
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-3900000000-4b439f0aa2820ea498c7
Mass Spectrum (Electron Ionization)MSsplash10-0a4l-4900000000-8b443325c415e154ac85
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Details1. Gamma-aminobutyric acid receptor subunit alpha-1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
  4. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details2. Gamma-aminobutyric acid receptor subunit alpha-2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details3. Gamma-aminobutyric acid receptor subunit alpha-3
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details4. Gamma-aminobutyric acid receptor subunit alpha-4
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA4
Uniprot ID
P48169
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-4
Molecular Weight
61622.645 Da
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details5. Gamma-aminobutyric acid receptor subunit alpha-5
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Transporter activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA5
Uniprot ID
P31644
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight
52145.645 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details6. Gamma-aminobutyric acid receptor subunit alpha-6
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA6
Uniprot ID
Q16445
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-6
Molecular Weight
51023.69 Da
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
  2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Details7. Neuronal acetylcholine receptor subunit alpha-4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Details8. Neuronal acetylcholine receptor subunit alpha-7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Details9. Glutamate receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ionotropic glutamate receptor activity
Specific Function
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name
GRIA2
Uniprot ID
P42262
Uniprot Name
Glutamate receptor 2
Molecular Weight
98820.32 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Details10. Glutamate receptor ionotropic, kainate 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Kainate selective glutamate receptor activity
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIK2
Uniprot ID
Q13002
Uniprot Name
Glutamate receptor ionotropic, kainate 2
Molecular Weight
102582.475 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Drug created at July 06, 2007 19:48 / Updated at September 28, 2021 21:54