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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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 g/LNot Available
LogP1.47HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+153.8631661259
DarkChem[M-H]-149.86131661259
DeepCCS[M+H]+161.75130932474
DeepCCS[M-H]-159.39330932474
DeepCCS[M-2H]-192.2830932474
DeepCCS[M+Na]+167.84430932474
AllCCS[M+H]+151.732859911
AllCCS[M+H-H2O]+147.732859911
AllCCS[M+NH4]+155.532859911
AllCCS[M+Na]+156.632859911
AllCCS[M-H]-153.432859911
AllCCS[M+Na-2H]-153.332859911
AllCCS[M+HCOO]-153.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenobarbitalCCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C13457.0Standard polar33892256
PhenobarbitalCCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C11949.0Standard non polar33892256
PhenobarbitalCCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C11958.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenobarbital,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O1880.7Semi standard non polar33892256
Phenobarbital,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O2074.1Standard non polar33892256
Phenobarbital,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O2938.0Standard polar33892256
Phenobarbital,2TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1796.9Semi standard non polar33892256
Phenobarbital,2TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2092.7Standard non polar33892256
Phenobarbital,2TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2568.9Standard polar33892256
Phenobarbital,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2141.2Semi standard non polar33892256
Phenobarbital,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2297.4Standard non polar33892256
Phenobarbital,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2996.1Standard polar33892256
Phenobarbital,2TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2302.6Semi standard non polar33892256
Phenobarbital,2TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2538.3Standard non polar33892256
Phenobarbital,2TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2723.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phenobarbital EI-B (Non-derivatized)splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenobarbital CI-B (Non-derivatized)splash10-001i-0090000000-55265fc1e12027dc64542017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenobarbital EI-B (Non-derivatized)splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenobarbital CI-B (Non-derivatized)splash10-001i-0090000000-55265fc1e12027dc64542018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenobarbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1940000000-8377cca722b6479ce2fd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenobarbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uxr-6950000000-193bf296d3e5d17056282014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOFsplash10-001i-0190000000-8cf53cd66a890256ea982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOFsplash10-001i-1290000000-73d0e0b25f99ffc6a5002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOFsplash10-0016-3950000000-ab62a9483b8a2a65b5632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOFsplash10-0006-0900000000-4121e8dd703c01c1161c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , negative-QTOFsplash10-0006-0900000000-4976dfc244184e5d627b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-001i-1890000000-a12eb2be0b05b9f234de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-03di-1920000000-43ed71cd16bfceef49e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-08fr-2900000000-236ae1dab83b15539a862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-053u-3900000000-2a994f0e45c022cca6402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-053u-4900000000-066a53ca113150f584062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-0uy3-8900000000-6bcd457bfff85f05fe9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-0udi-9500000000-0ecfff7e43e9e78d677e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital LC-ESI-QFT , positive-QTOFsplash10-0uxs-9300000000-7413ad1c764a1ae4a98e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital 75V, Negative-QTOFsplash10-0006-0900000000-4976dfc244184e5d627b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital 45V, Negative-QTOFsplash10-0016-3950000000-ab62a9483b8a2a65b5632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital 60V, Negative-QTOFsplash10-0006-0900000000-4121e8dd703c01c1161c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital 120V, Positive-QTOFsplash10-0uy3-8900000000-741b028c01a0bfefd0032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenobarbital 15V, Positive-QTOFsplash10-001i-0790000000-ab8562b536e84297ce372021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenobarbital 10V, Positive-QTOFsplash10-001i-0190000000-f722d696dc84bd92f7d22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenobarbital 20V, Positive-QTOFsplash10-03xr-0910000000-d76f47fd3df15d7ea2142016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenobarbital 40V, Positive-QTOFsplash10-014l-8910000000-29ca3dd7066d66bd04122016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenobarbital 10V, Negative-QTOFsplash10-0016-9670000000-ddcdac3a0cb816b2307c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenobarbital 20V, Negative-QTOFsplash10-0006-9610000000-315a80c916d24f8b59e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenobarbital 40V, Negative-QTOFsplash10-000x-9700000000-e2564ed7f0e6acd73e7b2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
Good Scents 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 ]