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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:21 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
Data?1582753281
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, phenylethylbarbituricHMDB
PhenylbarbitalHMDB
Phenobarbital sodiumHMDB
Phenobarbital, monosodium saltHMDB
GardenalHMDB
HystepsHMDB
Monosodium salt phenobarbitalHMDB
Sodium, phenobarbitalHMDB
PhenemalHMDB
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
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 g/LNot Available
LogP1.47HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.4ALOGPS
logP1.41ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.75 m³·mol⁻¹ChemAxon
Polarizability22.62 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd2017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0090000000-55265fc1e12027dc64542017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd2018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0090000000-55265fc1e12027dc64542018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1940000000-8377cca722b6479ce2fd2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uxr-6950000000-193bf296d3e5d17056282014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0190000000-8cf53cd66a890256ea982017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-1290000000-73d0e0b25f99ffc6a5002017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0016-3950000000-ab62a9483b8a2a65b5632017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-4121e8dd703c01c1161c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-4976dfc244184e5d627b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-1890000000-a12eb2be0b05b9f234de2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-1920000000-43ed71cd16bfceef49e62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-08fr-2900000000-236ae1dab83b15539a862017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-053u-3900000000-2a994f0e45c022cca6402017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-053u-4900000000-066a53ca113150f584062017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uy3-8900000000-6bcd457bfff85f05fe9c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-9500000000-0ecfff7e43e9e78d677e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxs-9300000000-7413ad1c764a1ae4a98e2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-f722d696dc84bd92f7d22016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0910000000-d76f47fd3df15d7ea2142016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-8910000000-29ca3dd7066d66bd04122016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0016-9670000000-ddcdac3a0cb816b2307c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9610000000-315a80c916d24f8b59e82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9700000000-e2564ed7f0e6acd73e7b2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)2014-09-23View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01174 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01174 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01174
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4599
KEGG Compound IDC07434
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenobarbital
METLIN IDNot Available
PubChem Compound4763
PDB IDNot Available
ChEBI ID8069
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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 ]