Phenytoin

Phenytoin
Clinical data
Pronunciation	/fəˈnɪtoʊɪn, ˈfɛnɪtɔɪn/
Trade names	Dilantin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682022
License data	US DailyMed: Phenytoin;
Pregnancy; category	AU: D; Toxic to reproduction;
Routes of; administration	By mouth, intravenous
Drug class	Anticonvulsant
ATC code	N03AB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	70–100% (oral), 24.4% (rectal)
Protein binding	95%
Metabolism	Liver
Onset of action	10–30 min (intravenous)
Elimination half-life	10–22 hours
Duration of action	24 hours
Excretion	Urinary (23–70%), bile
Identifiers
	IUPAC name 5,5-diphenylimidazolidine-2,4-dione;
CAS Number	57-41-0 ;
PubChem CID	1775;
IUPHAR/BPS	2624;
DrugBank	DB00252 ;
ChemSpider	1710 ;
UNII	6158TKW0C5;
KEGG	D00512 ;
ChEBI	CHEBI:8107 ;
ChEMBL	ChEMBL16 ;
CompTox Dashboard (EPA)	DTXSID8020541 ;
ECHA InfoCard	100.000.298
Chemical and physical data
Formula	C15H12N2O2
Molar mass	252.273 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C2(C(=O)NC(=O)N2)C3=CC=CC=C3;
	InChI InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19) ; Key:CXOFVDLJLONNDW-UHFFFAOYSA-N ;
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Phenytoin (PHT), sold under the brand name Dilantin among others, is an anti-seizure medication. It is useful for the prevention of tonic-clonic seizures (also known as grand mal seizures) and focal seizures, but not absence seizures. The intravenous form, fosphenytoin, is used for status epilepticus that does not improve with benzodiazepines. It may also be used for certain heart arrhythmias or neuropathic pain. It can be taken intravenously or by mouth. The intravenous form generally begins working within 30 minutes and is effective for roughly 24 hours. Blood levels can be measured to determine the proper dose.

Common side effects include nausea, stomach pain, loss of appetite, poor coordination, increased hair growth, and enlargement of the gums. Potentially serious side effects include sleepiness, self harm, liver problems, bone marrow suppression, low blood pressure, and toxic epidermal necrolysis. There is evidence that use during pregnancy results in abnormalities in the baby. It appears to be safe to use when breastfeeding. Alcohol may interfere with the medication's effects.

Phenytoin was first made in 1908 by the German chemist Heinrich Biltz and found useful for seizures in 1936. It is on the World Health Organization's List of Essential Medicines. Phenytoin is available as a generic medication. In 2020, it was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions.

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