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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Barbital
- Accession Number
- DB01483
- Type
- Small Molecule
- Groups
- Illicit
- Description
A long-acting barbiturate that depresses most metabolic processes at high doses. It is used as a hypnotic and sedative and may induce dependence. Barbital is also used in veterinary practice for central nervous system depression. Barbital is a schedule IV controlled drug.
- Structure
- Synonyms
- Not Available
- Categories
- Anticholinergic Agents
- Anticonvulsants
- Barbiturates
- Barbiturates, Plain
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 Enzyme Inducers
- GABA Agents
- GABA Modulators
- Hypnotics and Sedatives
- Nervous System
- Neurotransmitter Agents
- Nicotinic Antagonists
- Psycholeptics
- Pyrimidines
- Pyrimidinones
- UNII
- 5WZ53ENE2P
- CAS number
- 57-44-3
- Weight
- Average: 184.1925
Monoisotopic: 184.08479226 - Chemical Formula
- C8H12N2O3
- InChI Key
- FTOAOBMCPZCFFF-UHFFFAOYSA-N
- InChI
- InChI=1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
- IUPAC Name
- 5,5-diethyl-1,3-diazinane-2,4,6-trione
- SMILES
- CCC1(CC)C(=O)NC(=O)NC1=O
Pharmacology
- Indication
- Not Available
- Pharmacodynamics
- Not Available
- Mechanism of action
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
- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The metabolism of (R)-warfarin can be increased when combined with Barbital. (S)-Warfarin The metabolism of (S)-Warfarin can be increased when combined with Barbital. 1,10-Phenanthroline The therapeutic efficacy of Barbital can be decreased when used in combination with 1,10-Phenanthroline. 3-isobutyl-1-methyl-7H-xanthine The serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be decreased when it is combined with Barbital. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Barbital. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be increased when combined with Barbital. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Barbital. 5-androstenedione The metabolism of 5-androstenedione can be increased when combined with Barbital. 6-O-benzylguanine The serum concentration of 6-O-benzylguanine can be decreased when it is combined with Barbital. 7-Deazaguanine The serum concentration of 7-Deazaguanine can be decreased when it is combined with Barbital. - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- ATC Codes
- N05CA04 — Barbital
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 190 °C PhysProp boiling point (°C) 250 °C at 2.20E+01 mm Hg PhysProp water solubility 7460 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.65 HANSCH,C ET AL. (1995) logS -1.39 ADME Research, USCD pKa 8.14 (at 15 °C) KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 3.23 mg/mL ALOGPS logP 0.73 ALOGPS logP 0.72 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 8.48 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 2 ChemAxon Refractivity 44.25 m3·mol-1 ChemAxon Polarizability 17.59 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 + 0.955 Blood Brain Barrier + 0.9694 Caco-2 permeable - 0.6146 P-glycoprotein substrate Non-substrate 0.5238 P-glycoprotein inhibitor I Non-inhibitor 0.7826 P-glycoprotein inhibitor II Non-inhibitor 0.9964 Renal organic cation transporter Non-inhibitor 0.9395 CYP450 2C9 substrate Non-substrate 0.7915 CYP450 2D6 substrate Non-substrate 0.9074 CYP450 3A4 substrate Non-substrate 0.7823 CYP450 1A2 substrate Non-inhibitor 0.896 CYP450 2C9 inhibitor Non-inhibitor 0.9436 CYP450 2D6 inhibitor Non-inhibitor 0.9586 CYP450 2C19 inhibitor Non-inhibitor 0.918 CYP450 3A4 inhibitor Non-inhibitor 0.9723 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9847 Ames test AMES toxic 0.5531 Carcinogenicity Non-carcinogens 0.8532 Biodegradation Not ready biodegradable 0.9462 Rat acute toxicity 3.5489 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9913 hERG inhibition (predictor II) Non-inhibitor 0.9734
Spectra
- Mass Spec (NIST)
- Download (8.31 KB)
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - CI-B GC-MS splash10-000i-0900000000-90fb45d882d2c3ed038f GC-MS Spectrum - EI-B GC-MS splash10-052f-9400000000-fa1289872f9f35015abc GC-MS Spectrum - EI-B GC-MS splash10-052f-9500000000-856a7fe5dbfd28d00c38 GC-MS Spectrum - EI-B GC-MS splash10-0a4l-2900000000-42c0874d0bac13cc2d94 GC-MS Spectrum - EI-B GC-MS splash10-0a4u-5900000000-497f9ee367181a6df30a 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
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Barbituric acid derivatives
- Alternative Parents
- N-acyl ureas / Diazinanes / Dicarboximides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Barbiturate / N-acyl urea / Ureide / 1,3-diazinane / Dicarboximide / Urea / Carbonic acid derivative / Carboxylic acid derivative / Azacycle / Organic nitrogen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- barbiturates (CHEBI:31252)
Targets
- 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. [PubMed:14579514]
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
- 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. [PubMed:11264449]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- 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
- 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. [PubMed:11264449]
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
- 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
- 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. [PubMed:11264449]
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
- 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. [PubMed:10209232]
- 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
- 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. [PubMed:11264449]
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
- 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
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
- 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. [PubMed:11264449]
- 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. [PubMed:11264449]
- 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. [PubMed:16248797]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- 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. [PubMed:11264449]
- 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. [PubMed:16248797]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- 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. [PubMed:11264449]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- 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. [PubMed:11264449]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Nallani SC, Glauser TA, Hariparsad N, Setchell K, Buckley DJ, Buckley AR, Desai PB: Dose-dependent induction of cytochrome P450 (CYP) 3A4 and activation of pregnane X receptor by topiramate. Epilepsia. 2003 Dec;44(12):1521-8. [PubMed:14636322]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- Curator comments
- Barbital is a member of the barbiturate drug class. The majority of drugs in this class induce CYP2C19.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333]
- Yukawa E, Mamiya K: Effect of CYP2C19 genetic polymorphism on pharmacokinetics of phenytoin and phenobarbital in Japanese epileptic patients using Non-linear Mixed Effects Model approach. J Clin Pharm Ther. 2006 Jun;31(3):275-82. doi: 10.1111/j.1365-2710.2006.00712.x. [PubMed:16789993]
- Lee SM, Chung JY, Lee YM, Park MS, Namgung R, Park KI, Lee C: Effects of cytochrome P450 (CYP)2C19 polymorphisms on pharmacokinetics of phenobarbital in neonates and infants with seizures. Arch Dis Child. 2012 Jun;97(6):569-72. doi: 10.1136/archdischild-2011-300538. Epub 2012 Feb 13. [PubMed:22331680]
- Hukkanen J: Induction of cytochrome P450 enzymes: a view on human in vivo findings. Expert Rev Clin Pharmacol. 2012 Sep;5(5):569-85. doi: 10.1586/ecp.12.39. [PubMed:23121279]
- Ioannides C. (2008). Cytochromes P450. RSC Publishing.
- Phenobarbital Monograph [File]
Drug created on July 31, 2007 07:09 / Updated on November 02, 2018 05:01