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Phenytoin information


Phenytoin
Structural formula of phenytoin
Ball-and-stick model of the phenytoin molecule
Clinical data
Pronunciation/fəˈnɪtɪn, ˈfɛnɪtɔɪn/
Trade namesDilantin, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682022
License data
  • US DailyMed: Phenytoin
Pregnancy
category
  • AU: D
  • Toxic to reproduction
Routes of
administration
By mouth, intravenous
Drug classAnticonvulsant
ATC code
  • N03AB02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[2]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability70–100% (oral), 24.4% (rectal)
Protein binding95%[3]
MetabolismLiver
Onset of action10–30 min (intravenous)[4]
Elimination half-life10–22 hours[3]
Duration of action24 hours[4]
ExcretionUrinary (23–70%), bile[5]
Identifiers
IUPAC name
  • 5,5-diphenylimidazolidine-2,4-dione
CAS Number
  • 57-41-0 checkY
PubChem CID
  • 1775
IUPHAR/BPS
  • 2624
DrugBank
  • DB00252 checkY
ChemSpider
  • 1710 checkY
UNII
  • 6158TKW0C5
KEGG
  • D00512 checkY
ChEBI
  • CHEBI:8107 ☒N
ChEMBL
  • ChEMBL16 ☒N
CompTox Dashboard (EPA)
  • DTXSID8020541 Edit this at Wikidata
ECHA InfoCard100.000.298 Edit this at Wikidata
Chemical and physical data
FormulaC15H12N2O2
Molar mass252.273 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) ☒N
  • Key:CXOFVDLJLONNDW-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Phenytoin (PHT), sold under the brand name Dilantin among others,[1] is an anti-seizure medication.[3] It is useful for the prevention of tonic-clonic seizures (also known as grand mal seizures) and focal seizures, but not absence seizures.[3] The intravenous form, fosphenytoin, is used for status epilepticus that does not improve with benzodiazepines.[3] It may also be used for certain heart arrhythmias or neuropathic pain.[3] It can be taken intravenously or by mouth.[3] The intravenous form generally begins working within 30 minutes and is effective for roughly 24 hours.[4] Blood levels can be measured to determine the proper dose.[3]

Common side effects include nausea, stomach pain, loss of appetite, poor coordination, increased hair growth, and enlargement of the gums.[3] Potentially serious side effects include sleepiness, self harm, liver problems, bone marrow suppression, low blood pressure, and toxic epidermal necrolysis.[3] There is evidence that use during pregnancy results in abnormalities in the baby.[3] It appears to be safe to use when breastfeeding.[3] Alcohol may interfere with the medication's effects.[3]

Phenytoin was first made in 1908 by the German chemist Heinrich Biltz and found useful for seizures in 1936.[6][7] It is on the World Health Organization's List of Essential Medicines.[8] Phenytoin is available as a generic medication.[9] In 2020, it was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[10][11]

  1. ^ a b Cite error: The named reference genericnames was invoked but never defined (see the help page).
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ a b c d e f g h i j k l m "Phenytoin". The American Society of Health-System Pharmacists. Archived from the original on 2015-09-08. Retrieved Aug 22, 2015.
  4. ^ a b c Marx JA (2010). Rosen's emergency medicine: concepts and clinical practice (7th ed.). Philadelphia: Mosby/Elsevier. p. 1352. ISBN 9780323054720.
  5. ^ Parker KD, Elliott HW, Wright JA, Nomof N, Hine CH (March 1970). "Blood and urine concentrations of subjects receiving barbiturates, meprobamate, glutethimide, or diphenylhydantoin". Clinical Toxicology. 3 (1). Informa UK Limited: 131–145. doi:10.3109/15563657008990108. PMID 5520387.
  6. ^ Aicardi J (2008). Epilepsy : a comprehensive textbook (2nd ed.). Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 1431. ISBN 9780781757775.
  7. ^ Wolfson AB (2010). Harwood-Nuss' clinical practice of emergency medicine (5th ed.). Philadelphia, PA: Lippincott Williams & Wilkins. p. 1415. ISBN 9780781789431. Retrieved 9 June 2016.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ Hamilton RJ (2013). Tarascon pocket pharmacopoeia (14 ed.). Burlington, MA.: Jones & Bartlett Learning. p. 294. ISBN 9781449673635.
  10. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  11. ^ "Phenytoin - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.

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Phenytoin

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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...

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Fosphenytoin

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water-soluble phenytoin prodrug that is administered intravenously to deliver phenytoin, potentially more safely than intravenous phenytoin. It is used...

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Carbamazepine

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second-line agent in bipolar disorder. Carbamazepine appears to work as well as phenytoin and valproate for focal and generalized seizures. It is not effective...

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Craniotomy

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anti-seizure medications post operatively. Traditionally this has been phenytoin, but now is increasingly levetiracetam as it has a lower risk of drug-drug...

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Euthanasia solution

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cardiac arrest. Sodium channel blockers, like benzocaine, lidocaine, phenytoin, and tricaine methanesulfonate, are regularly used to produce rapid local...

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Fetal hydantoin syndrome

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fetus by exposure to teratogenic effects of phenytoin. Dilantin is the brand name of the drug phenytoin sodium in the United States, commonly used in...

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Anticonvulsant

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Phenobarbital was the main anticonvulsant from 1912 until the development of phenytoin in 1938. Today, phenobarbital is rarely used to treat epilepsy in new...

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Drug rash with eosinophilia and systemic symptoms

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recognized as the DRESS syndrome. For example, anticonvulsants in the 1930s, phenytoin in 1950, and other medications in the ensuing years were reported to do...

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Hyperpigmentation

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Hyperpigmentation is the darkening of an area of skin or nails caused by increased melanin. Hyperpigmentation can be caused by sun damage, inflammation...

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Status epilepticus

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Benzodiazepines are the preferred initial treatment, after which typically phenytoin is given. Possible benzodiazepines include intravenous lorazepam as well...

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Gingival enlargement

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a common side effect of phenytoin, termed "Phenytoin-induced gingival overgrowth" (PIGO). anticonvulsants (such as phenytoin, phenobarbital, lamotrigine...

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Clonazepam

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benefits, though, tended to be transient in many people, and the addition of phenytoin for lasting control was required in these patients. It is also approved...

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Epilepsy

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number of medications available including phenytoin, carbamazepine and valproate. Evidence suggests that phenytoin, carbamazepine, and valproate may be equally...

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Methamphetamine

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Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan...

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Sultiame

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ability to raise the blood levels of phenytoin, it was assumed that sultiame would only act in combination with phenytoin. This finding, together with the...

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Diazepam

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and antipsychotics, as well as anticonvulsants such as phenobarbital, phenytoin, and carbamazepine. The euphoriant effects of opioids may be increased...

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Purple glove syndrome

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epilepsy drug phenytoin. Compartment syndrome is a complication of PGS. Purple glove syndrome is caused by the intravenous anticonvulsant phenytoin. This medication...

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Peripheral neuropathy

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with no known cause. Toxic causes: drugs (vincristine, metronidazole, phenytoin, nitrofurantoin, isoniazid, ethyl alcohol, statins),[medical citation...

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MDMA

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Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan...

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Lamotrigine

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spectrum of action than other sodium channel antiepileptic drugs such as phenytoin and is effective in the treatment of the depressed phase of bipolar disorder...

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Pentobarbital

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It is taken alone, or in combination with complementary agents such as phenytoin, in commercial animal euthanasia injectable solutions. In the Netherlands...

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Primidone

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effective in the treatment of epilepsy. Primidone has been compared to phenytoin, phenobarbital, mephobarbital, ethotoin, metharbital, and mephenytoin...

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Lorazepam

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epilepticus. Lorazepam is more effective than diazepam and intravenous phenytoin in the treatment of status epilepticus and has a lower risk of continuing...

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Ketamine

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Licarbazepine Mephenytoin Oxcarbazepine Oxitriptyline Phenacemide Pheneturide Phenytoin Rufinamide Sipatrigine Topiramate Sodium valproate Valnoctamide Valproate...

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Asterixis

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contraleteral one-sided asterixis. Some drugs, particularly phenytoin (when it is known as phenytoin flap). Other drugs implicated include benzodiazepines,...

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Glossary of chemical formulae

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C15H10O7 quercetin 117-39-5 C15H12N2O carbamazepine 298-46-4 C15H12N2O2 phenytoin 57-41-0 C15H13NO4 Darienine 111316-27-9 C15H18O2 Curzerenone 20493-56-5...

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PE

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Penis enlargement Phenylephrine, a common over-the-counter decongestant Phenytoin equivalent, used to measure doses of fosphenytoin Physical exercise Prolonged...

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body, amounting to pharmacokinetic interactions such as: Rifampicin, phenytoin, carbamazepine and other inducers of the liver enzyme CYP3A4 speed up...

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