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
Structure for Amobarbital (DB01351)
- 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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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 potentiatorHumans AGamma-aminobutyric acid receptor subunit alpha-2 potentiatorHumans AGamma-aminobutyric acid receptor subunit alpha-3 potentiatorHumans AGamma-aminobutyric acid receptor subunit alpha-4 potentiatorHumans AGamma-aminobutyric acid receptor subunit alpha-5 potentiatorHumans AGamma-aminobutyric acid receptor subunit alpha-6 potentiatorHumans UNeuronal acetylcholine receptor subunit alpha-4 antagonistHumans UNeuronal acetylcholine receptor subunit alpha-7 antagonistHumans UGlutamate receptor 2 antagonistHumans UGlutamate receptor ionotropic, kainate 2 antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Amobarbital is combined with 1,2-Benzodiazepine. Abaloparatide Amobarbital may increase the hypotensive activities of Abaloparatide. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Amobarbital. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Amobarbital. Acebutolol Amobarbital may increase the hypotensive activities of Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Amobarbital. Acetaminophen The metabolism of Acetaminophen can be increased when combined with Amobarbital. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Amobarbital. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Amobarbital. Aclidinium The risk or severity of adverse effects can be increased when Amobarbital is combined with Aclidinium. 
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- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Amobarbital sodium G0313KNC7D 64-43-7 BNHGKKNINBGEQL-UHFFFAOYSA-M - International/Other Brands
- Amytal / Isomytal
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Amytal Sodium Injection, powder, lyophilized, for solution 0.5 g/5mL Intramuscular; Intravenous Marathon Pharmaceuticals 2008-09-25 2016-03-31 US 
Amytal Sodium Injection, powder, lyophilized, for solution 0.5 g/5mL Intramuscular; Intravenous Bausch Health US LLC 2008-09-25 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Tuinal Pulvule 303 Amobarbital sodium (50 mg) + Secobarbital sodium (50 mg) Capsule Oral Pharmascience Inc 1945-12-31 2004-03-05 Canada 
Tuinal Pulvule 304 Amobarbital sodium (100 mg / cap) + Secobarbital sodium (100 mg / cap) Capsule Oral Pharmascience Inc 1945-12-31 2004-03-05 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Amytal Sodium Amobarbital sodium (0.5 g/5mL) Injection, powder, lyophilized, for solution Intramuscular; Intravenous Marathon Pharmaceuticals 2008-09-25 2016-03-31 US Amytal Sodium Amobarbital sodium (0.5 g/5mL) Injection, powder, lyophilized, for solution Intramuscular; Intravenous Bausch Health US LLC 2008-09-25 Not applicable US
Categories
- ATC Codes
- N05CA02 — AmobarbitalN05CB01 — Combinations of barbiturates
- Drug Categories
- Anticholinergic Agents
- Anticonvulsants
- Barbiturates
- Barbiturates, Plain
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- GABA Agents
- GABA Modulators
- Hypnotics and Sedatives
- Nervous System
- Neurotransmitter Agents
- Nicotinic Antagonists
- Psycholeptics
- Pyrimidines
- Pyrimidinones
- 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
- 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]
- Maynert EW: The alcoholic metabolites of pentobarbital and amobarbital in man. J Pharmacol Exp Ther. 1965 Oct;150(1):118-21. [Article]
- 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]
- 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]
- McCall WV: The addition of intravenous caffeine during an amobarbital interview. J Psychiatry Neurosci. 1992 Nov;17(5):195-7. [Article]
- External Links
- Human Metabolome Database
- HMDB0015440
- KEGG Drug
- D00555
- KEGG Compound
- C07536
- PubChem Compound
- 2164
- PubChem Substance
- 46508165
- ChemSpider
- 2079
- 719
- ChEBI
- 2673
- ChEMBL
- CHEMBL267894
- ZINC
- ZINC000004811698
- Therapeutic Targets Database
- DAP000686
- PharmGKB
- PA448401
- Wikipedia
- Amobarbital
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1, 2 Recruiting Treatment Osteoarthritis (OA) / Posttraumatic Osteoarthritis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- AAIPharma Inc.
- Marathon Pharmaceuticals
- Ranbaxy Laboratories
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intramuscular; Intravenous 0.5 g/5mL Powder, for solution Intramuscular; Intravenous 500 mg / amp Capsule Oral 60 mg / cap Capsule Oral 200 mg / cap Capsule Oral - Prices
Unit description Cost Unit Amytal sodium 0.5 gram vial 117.35USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 157 °C PhysProp water solubility 603 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.07 HANSCH,C ET AL. (1995) logS -2.57 ADME Research, USCD pKa 7.84 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.897 mg/mL ALOGPS logP 1.87 ALOGPS logP 1.89 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 7.48 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 75.27 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 58 m3·mol-1 Chemaxon Polarizability 23.45 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9254 Blood Brain Barrier + 0.949 Caco-2 permeable - 0.5913 P-glycoprotein substrate Substrate 0.6471 P-glycoprotein inhibitor I Non-inhibitor 0.5906 P-glycoprotein inhibitor II Non-inhibitor 0.9426 Renal organic cation transporter Non-inhibitor 0.9307 CYP450 2C9 substrate Non-substrate 0.7591 CYP450 2D6 substrate Non-substrate 0.9011 CYP450 3A4 substrate Non-substrate 0.663 CYP450 1A2 substrate Non-inhibitor 0.879 CYP450 2C9 inhibitor Non-inhibitor 0.7603 CYP450 2D6 inhibitor Non-inhibitor 0.9299 CYP450 2C19 inhibitor Non-inhibitor 0.7269 CYP450 3A4 inhibitor Non-inhibitor 0.9422 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9105 Ames test Non AMES toxic 0.691 Carcinogenicity Non-carcinogens 0.8925 Biodegradation Not ready biodegradable 0.944 Rat acute toxicity 2.9884 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9852 hERG inhibition (predictor II) Non-inhibitor 0.8963
Spectra
- Mass Spec (NIST)
- Download (8.4 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - CI-B GC-MS splash10-004i-0090000000-5962005393da49f25b6d GC-MS Spectrum - EI-B GC-MS splash10-0a4l-3900000000-4b439f0aa2820ea498c7 Mass Spectrum (Electron Ionization) MS splash10-0a4l-4900000000-8b443325c415e154ac85 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [Article]
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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
- 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
- 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
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
- 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
- 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
- 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
- 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]
- 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]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
- 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
- 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]
- 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]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
- 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
- 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]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
- 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
- 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]
- 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