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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:32:19 UTC
HMDB IDHMDB15305
Secondary Accession NumbersNone
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
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 KeyInChIKey=DDBREPKUVSBGFI-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
  • Benzenoid
  • 1,3-diazinane
  • Monocyclic benzene moiety
  • Urea
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
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 QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01174
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01174
  • Not Applicable
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 LinkHMDB15305
Metagene LinkHMDB15305
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. [11687150 ]
  2. Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [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. [15329080 ]
  4. Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [15495087 ]
  5. Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [16142991 ]