Phenobarbital

Phenobarbital, also known as phenobarbitone or phenobarb, sold under the brand name Luminal among others, is a medication of the barbiturate type. It is recommended by the World Health Organization (WHO) for the treatment of certain types of epilepsy in developing countries. In the developed world, it is commonly used to treat seizures in young children, while other medications are generally used in older children and adults. In developed countries it is used for veterinary purposes. It may be used intravenously, injected into a muscle, or taken by mouth. The injectable form may be used to treat status epilepticus. Phenobarbital is occasionally used to treat trouble sleeping, anxiety, and drug withdrawal and to help with surgery. It usually begins working within five minutes when used intravenously and half an hour when administered by mouth. Its effects last for between four hours and two days.

Phenobarbital
Clinical data
Trade namesLuminal, Sezaby
AHFS/Drugs.comMonograph
MedlinePlusa682007
Pregnancy
category
  • AU: D
Dependence
liability
Low
Routes of
administration
By mouth, rectal, parenteral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability>95%
Protein binding20 to 45%
MetabolismLiver (mostly CYP2C19)
Onset of actionwithin 5 min (IV) and 30 min (PO)
Elimination half-life53 to 118 hours
Duration of action4 hrs to 2 days
ExcretionKidney and fecal
Identifiers
  • 5-Ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.007
Chemical and physical data
FormulaC12H12N2O3
Molar mass232.239 g·mol−1
3D model (JSmol)
  • O=C1NC(=O)NC(=O)C1(c2ccccc2)CC
  • 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) Y
  • Key:DDBREPKUVSBGFI-UHFFFAOYSA-N Y
  (verify)

Side effects include a decreased level of consciousness along with a decreased effort to breathe. There is concern about both abuse and withdrawal following long-term use. It may also increase the risk of suicide. It is pregnancy category B or D (depending on how it is taken) in the United States and category D in Australia, meaning that it may cause harm when taken by pregnant women. If used during breastfeeding it may result in drowsiness in the baby. A lower dose is recommended in those with poor liver or kidney function, as well as elderly people. Phenobarbital, like other barbiturates works by increasing the activity of the inhibitory neurotransmitter GABA.

Phenobarbital was discovered in 1912 and is the oldest still commonly used anti-seizure medication. It is on the World Health Organization's List of Essential Medicines.

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