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Phenobarbital

July 24, 2017
Common Name

Phenobarbital Description

Phenobarbital is only found in individuals that have used or taken this drug. It is a barbituric acid derivative that acts as a nonselective central nervous system depressant.Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resliting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the reslit of its effect on the polysynaptic midbrain reticliar formation, which controls CNS arousal. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI 5-Ethyl-5-phenyl-pyrimidine-2,4,6-trioneChEBI 5-Ethyl-5-phenylbarbituric acidChEBI 5-Ethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trioneChEBI 5-Phenyl-5-ethylbarbituric acidChEBI LuminalChEBI PhenobarbitolChEBI PhenobarbitoneChEBI Phenobarbituric acidChEBI PhenylaethylbarbitursaeureChEBI PhenylethylbarbiturateChEBI Phenylethylbarbituric acidChEBI PhenylethylbarbitursaeureChEBI PHENYLETHYLMALONYLUREAChEBI 5-Ethyl-5-phenylbarbitateGenerator 5-Ethyl-5-phenylbarbitic acidGenerator 5-Phenyl-5-ethylbarbitateGenerator 5-Phenyl-5-ethylbarbitic acidGenerator PhenobarbitateGenerator Phenobarbitic acidGenerator PhenylethylbarbitateGenerator Phenylethylbarbitic acidGenerator FenobarbitalHMDB Acid, phenylethylbarbituricMeSH PhenylbarbitalMeSH Phenobarbital sodiumMeSH Phenobarbital, monosodium saltMeSH GardenalMeSH HystepsMeSH Monosodium salt phenobarbitalMeSH Sodium, phenobarbitalMeSH PhenemalMeSH

Chemical Formlia

C12H12N2O3 Average Molecliar Weight

232.2353 Monoisotopic Molecliar Weight

232.08479226 IUPAC Name

5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione Traditional Name

phenobarbital CAS Registry Number

50-06-6 SMILES

CCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)

InChI Key

DDBREPKUVSBGFI-UHFFFAOYSA-N Chemical 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
  • Benzene and substituted derivatives
  • Dicarboximides
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Barbiturate
  • Ureide
  • N-acyl urea
  • Monocyclic benzene moiety
  • 1,3-diazinane
  • Benzenoid
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • barbiturates (CHEBI:8069 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

  • Drug metabolite

    • Biofunction

  • Anticonvlisants
  • Excitatory Amino Acid Antagonists
  • GABA Modliators
  • Hypnotics and Sedatives
  • Waste products

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point174 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.76e-01 g/LNot Available LogP1.47HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.28 mg/mLALOGPS logP1.4ALOGPS logP1.41ChemAxon logS-2.9ALOGPS pKa (Strongest Acidic)8.14ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area75.27 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity59.75 m3·mol-1ChemAxon Polarizability22.61 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-001i-0190000000-8cf53cd66a890256ea98View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-001i-1290000000-73d0e0b25f99ffc6a500View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0016-3950000000-ab62a9483b8a2a65b563View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0006-0900000000-4121e8dd703c01c1161cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0006-0900000000-4976dfc244184e5d627bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-001i-1890000000-a12eb2be0b05b9f234deView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-03di-1920000000-43ed71cd16bfceef49e6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-08fr-2900000000-236ae1dab83b15539a86View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-053u-3900000000-2a994f0e45c022cca640View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-053u-4900000000-066a53ca113150f58406View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0uy3-8900000000-6bcd457bfff85f05fe9cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-9500000000-0ecfff7e43e9e78d677eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0uxs-9300000000-7413ad1c764a1ae4a98eView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-0uxr-6950000000-193bf296d3e5d1705628View in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

  • Kidney
  • Liver

    • Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01174

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01174

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-4 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01174 DrugBank Metabolite ID

    DBMET00285 Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4599 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Phenobarbital NuGOwiki Link

    HMDB15305 Metagene Link

    HMDB15305 METLIN ID

    Not Available PubChem Compound

    4763 PDB ID

    Not Available ChEBI ID

    8069

    Product: Kauniolide

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. [PubMed:11687150 ]
    2. Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [PubMed:12535420 ]
    3. Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. [PubMed:15329080 ]
    4. Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [PubMed:15495087 ]
    5. Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [PubMed:16142991 ]

    PMID: 16847438

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