File:Fenobarbital.jpg · Wikimedia Commons · See Wikimedia Commons
phenobarbital
Sign in to saveAlso known as phenylethylbarbiturate, 5-ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-ethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione, luminal, 5-phenyl-5-ethylbarbituric acid, 5-ethyl-5-phenylbarbituric acid, phenobarbituric acid, phenylethylbarbituric acid
Phenobarbital, also known as phenobarbitone, 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. It is also used for veterinary purposes.
OverviewAI-generated
Phenobarbital is a chemical compound with the formula C₁₂H₁₂N₂O₃. Its IUPAC name is 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione. The substance has a mass of 232.084792 and a weight of 232.23. It features a charge of 0, an xlogp value of 1.5, and a topological polar surface area of 75.3. The molecule contains two hydrogen bond donors and three hydrogen bond acceptors.
The compound is associated with a PubMed query count of 26609. It is referenced by 1,374 other encyclopedia articles. The stylized name for the compound is PHENobarbital.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.verifiedrevid
- 464200457
- Drug.image
- Phenobarbital2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 120
- Drug.alt
- 2D chemical structure of phenobarbital
- Drug.image2
- Phenobarbital 3D xtal ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 140
- Drug.alt2
- 3D ball-and-stick model of phenobarbital
- Drug.tradename
- Luminal, Sezaby, others
- Drug.MedlinePlus
- a682007
- Drug.DailyMedID
- Phenobarbital
- Drug.pregnancy_AU
- D
- Drug.dependency_liability
- High
- Drug.routes_of_administration
- By mouth, rectal, parenteral
- Drug.class
- Barbiturate
- Drug.ATC_prefix
- N03
- Drug.ATC_suffix
- AA02
via Wikipedia infobox
Chemical data
- Formula
- C12H12N2O3
- Molecular weight
- 232.23 g/mol
- IUPAC name
- 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
- SMILES
- CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2
- InChIKey
- DDBREPKUVSBGFI-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 75.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
26,609 papers- Acute phenobarbital intoxication.Southern medical journal · 1992
- Phenobarbital: biopharmacology.Advances in neurology · 1980
- Phenobarbital plasma levels in neonates.Clinics in perinatology · 1975
- Phenobarbital: binding.Advances in neurology · 1980
- Phenobarbital dyskinesia.Postgraduate medical journal · 1978
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 232.084792
- Has use
- medication
Show 10 more facts
- medical condition treated
- status epilepticus
- subject has role
- essential medicine
- chemical formula
- C₁₂H₁₂N₂O₃
- Commons category
- Phenobarbital
- canonical SMILES
- CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2
- World Health Organisation international non-proprietary name
- phenobarbital
- physically interacts with
- nuclear receptor subfamily 1 group I member 2
- different from
- (RS)-pentobarbital
- significant drug interaction
- sufentanil
- stylized name
- PHENobarbital
Sources (8)
via Wikidata · CC0
~16 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Other uses
- Side effects
- Contraindications
- Overdose
- Mechanism of action
- Pharmacokinetics
- History
- Society and culture
- Names
- Synthesis
- Regulation
- Selected overdoses
- Veterinary uses
- References
Phenobarbital, also known as phenobarbitone, 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. It is also used for veterinary purposes.
It may be administered by slow intravenous infusion (IV infusion), intramuscularly (IM), or orally (swallowed by mouth). Subcutaneous administration is not recommended. The IV or IM (injectable forms) may be used to treat status epilepticus if other drugs fail to achieve satisfactory results. Phenobarbital is occasionally used to treat insomnia, anxiety, and benzodiazepine withdrawal (as well as withdrawal from certain other drugs in specific circumstances), and prior to surgery as an anxiolytic and to induce sedation. It usually begins working within five minutes when used intravenously and half an hour when administered orally. Its effects last for between four hours and two days.
Excerpted from Wikipedia’s “phenobarbital” article, available under the CC BY-SA 4.0 licence.