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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-08-15 22:14:04 UTC
HMDB IDHMDB0015305
Secondary Accession Numbers
  • HMDB15305
Metabolite Identification
Common NamePhenobarbital
DescriptionPhenobarbital 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, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal.
Structure
Thumb
Synonyms
ValueSource
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 FormulaC12H12N2O3
Average Molecular Weight232.2353
Monoisotopic Molecular Weight232.08479226
IUPAC Name5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
Traditional Namephenobarbital
CAS Registry Number50-06-6
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 KeyDDBREPKUVSBGFI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
  • Drug metabolite
Biofunction
  • Anticonvulsants
  • Excitatory Amino Acid Antagonists
  • GABA Modulators
  • Hypnotics and Sedatives
  • Waste products
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.76e-01 g/LNot Available
LogP1.47HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0190000000-8cf53cd66a890256ea98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-1290000000-73d0e0b25f99ffc6a500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0016-3950000000-ab62a9483b8a2a65b563View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-4121e8dd703c01c1161cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-4976dfc244184e5d627bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-1890000000-a12eb2be0b05b9f234deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-1920000000-43ed71cd16bfceef49e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-08fr-2900000000-236ae1dab83b15539a86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-053u-3900000000-2a994f0e45c022cca640View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-053u-4900000000-066a53ca113150f58406View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uy3-8900000000-6bcd457bfff85f05fe9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-9500000000-0ecfff7e43e9e78d677eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxs-9300000000-7413ad1c764a1ae4a98eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0uxr-6950000000-193bf296d3e5d1705628View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01174 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01174 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01174
DrugBank Metabolite IDDBMET00285
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4599
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenobarbital
NuGOwiki LinkHMDB0015305
METLIN IDNot Available
PubChem Compound4763
PDB IDNot Available
ChEBI ID8069
References
Synthesis ReferenceNot 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 ]