Substance
ID:1049
Names and Identifiers
Brand Name
StarilettaeTridezibarbiturSedonalSolfoton TalphenoSombutolSomnolensSomnosanSpasepilinPhenobarbylPhenoluricPolcominalPromptonalSedabarSedizorinLepinalettenLiquitalLubergalLumesynNirvonalNova-PhenoHaplosHypnetteHypnoltolLefebarLeonalLepinalEnsodormEpidormEpisedalEpsyloneEtilfenFenemalCalminalCardenalChinoinDezibarbiturDoscalunEnsobarbSomonalStentalTeolaxinZadonalBarbiphenSinoratoxStental ExtentabsTalphenoTeoloxinTriabarbTriphenatolVersomnalPhenolurioSedlynSedofenSedonettesSolu-BarbSomnolettenLuphenilMolinalNeurobarbNoptilPhen-BarPhenemalumHennolettenHenotalHypnalettenHypnoloneLumenLumofridettenEpanalEpilolEskabarbFenylettaeBarbophenZadolettenBartolCoronalettaCratecilDunerylAephenalStarifenAphenylbarbitThenobarbitalBarbitaTheoloxinSedicatSevenalPhenylettenPhenyralSeda-TablinenSolfotonNunolPharmettenPhenaemalPhenemalPhenometPhobLuminalLuraminParkotalPhenobalPhenonylPhenoturicHypno-TablinettenHypnogenHystepsLephebarLinasenLixophenDamoralDormiralDormitalFenbitalGlysolettenHelionalLumesettesBarbenylBarbivisBarbonalCabronalCalmettenEunerylFenosedGardenalGardepanylHaplopanLubrokalBarbipilBardormBialminalBlu-PhenCodibarbitaDorminaAdonalAgrypnalAmylofeneAphenylettenBarbinalBarbiphenyl
IUPAC name
5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
Synonyms
Phenobarbituric AcidPhenobarbitalPhenylethylbarbituratePhenylethylbarbituric AcidPhenylethylmalonylureaFenobarbitalPhenobarbitolPhenobarbitone
IUPAC Traditional name
phenobarbital
Properties
Physical Property
Hydrophobicity(logP)
1.47 [HANSCH,C ET AL. (1995)]
Solubility
1.11 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Molecule Details
Drug Groups
approved
Description
A barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. [PubChem]
Indication
For the treatment of all types of seizures except absence seizures.
Pharmacology
Phenobarbital, the longest-acting barbiturate, is used for its anticonvulsant and sedative-hypnotic properties in the management of all seizure disorders except absence (petit mal).
Toxicity
CNS and respiratory depression which may progress to Cheyne-Stokes respiration, areflexia, constriction of the pupils to a slight degree (though in severe poisoning they may wshow paralytic dilation), oliguria, tachycardia, hypotension, lowered body temperature, and coma. Typical shock syndrome (apnea, circulatory collapse, respiratory arrest, and death) may occur.
Affected Organisms
Humans and other mammals
Biotransformation
Hepatic (mostly via CYP2C19).
Absorption
Absorbed in varying degrees following oral, rectal or parenteral administration. The salts are more rapidly absorbed than are the acids. The rate of absorption is increased if the sodium salt is ingested as a dilute solution or taken on an empty stomach.
Half Life
53 to 118 hours (mean 79 hours)
Protein Binding
20 to 45%
References
•
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]
•
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]
•
Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904.
[Pubmed]
•
Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68.
[Pubmed]
•
Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• 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
• Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. Pubmed
• 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
• Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. Pubmed
• Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. Pubmed