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Encyclopedia > Phenytoin
Phenytoin chemical structure
Phenytoin
Systematic (IUPAC) name
5,5-diphenylimidazolidine-2,4-dione
Identifiers
CAS number 57-41-0
ATC code N03AB02 N03AB04, N03AB05
PubChem 1775
DrugBank APRD00241
Chemical data
Formula C15H12N2O2
Mol. weight 252.268 g/mol
Pharmacokinetic data
Bioavailability 70-100% oral, 24.4% for rectal and intravenous administration
Metabolism hepatic
Half life 22 hours
Excretion Primarily through the bile
Therapeutic considerations
Pregnancy cat.

D Image File history File links Image is drawn in bkchem and GIMP. File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Metabolism (from Greek μεταβολισμός metabolismos) is the biochemical modification of chemical compounds in living organisms and cells. ... The liver is an organ in vertebrates including humans. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes Oral, parenteral

Phenytoin sodium (marketed as Dilantin® in the USA and as Epanutin® in the UK, by Parke-Davis, now part of Pfizer) is a commonly used antiepileptic. It was approved by the Food and Drug Administration in 1953 for use in seizures. Phenytoin acts to damp the unwanted, runaway brain activity seen in seizure by reducing electrical conductance among brain cells. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Parke-Davis was a pharmaceutical company which was previously a subsidiary of Warner-Lambert prior to Warner-Lamberts acquisition by Pfizer in 2000. ... Pfizer, Incorporated (NYSE: PFE), is the worlds largest pharmaceutical company based in New York City. ... The anticonvulsants, sometimes also called antiepileptics, belong to a diverse group of pharmaceuticals used in prevention of the occurrence of epileptic seizures. ... This article or section is in need of attention from an expert on the subject. ... 1953 (MCMLIII) was a common year starting on Thursday (link is to a full 1953 calendar). ... This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ...

Contents

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History

Phenytoin (diphenylhydantoin) was first synthesized by a German physician named Heinrich Biltz in 1908. Biltz sold his discovery to Parke-Davis, which did not find an immediate use for it. In 1938, outside scientists including H. Houston Merritt and Tracy Putnam discovered phenytoin's usefulness for controlling seizures, without the sedation effects associated with phenobarbital. There are some indications that phenytoin has other effects, including anxiety control and mood stabilization, although it has never been approved for those purposes by the FDA. 1908 (MCMVIII) was a leap year starting on Wednesday (link will take you to calendar). ... 1938 (MCMXXXVIII) was a common year starting on Saturday (link will take you to calendar). ... H. Houston Merritt (1902-1979) was one of the pre-eminent academic neurologists of his day. ... This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ... Phenobarbital (also phenobarbitone) (Luminal®) is a weak acid with the chemical formula C12H12N2O3. ... Anxiety is a complex combination of emotions that includes fear, apprehension and worry, and is often accompanied by physical sensations such as palpitations, nausea, chest pain and/or shortness of breath. ... A mood stabilizer is a psychiatric medication used to treat mood disorders characterized by rapid and unstable mood shifts. ...


Jack Dreyfus, founder of the Dreyfus Fund, became a major proponent of phenytoin as a means to control nervousness and depression when he received a prescription for Dilantin in 1966. Dreyfus' book about his experience with phenytoin, A Remarkable Medicine Has Been Overlooked, sits on the shelves of many physicians courtesy of the work of his foundation. Despite more than $70 million in personal financing, his push to see phenytoin evaluated for alternative uses has had little lasting effect on the medical community. This was partially due to Parke-Davis's reluctance to invest in a drug nearing the end of its patent life, and partially due to mixed results from various studies. Jack Dreyfus, was the founder of the Dreyfus Fund, and is widely publicized for being the man who invented the commonplace mutual fund[citation needed]. After selling the fund during the early 1970s he became a major proponent of phenytoin as a means to control nervousness and depression when... Clinical depression (also called severe depression disorder, major depression disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... 1966 (MCMLXVI) was a common year starting on Saturday (the link is to a full 1966 calendar). ...


Dilantin made an appearance in the 1962 novel One Flew Over the Cuckoo's Nest by Ken Kesey, both as an anticonvulsant and as a mechanism to control inmate behavior. One Flew Over the Cuckoos Nest (Paperback Edition) One Flew Over the Cuckoos Nest (1962) is a fiction novel by Ken Kesey. ... Ken Kesey - 1970 By Robert Altman Ken Elton Kesey (September 17, 1935 – November 10, 2001) was an American author, best known for his novel, One Flew Over the Cuckoos Nest, and as a (counter) cultural figure who, some consider, was a link between the beat generation of the 1950s... The anticonvulsants, sometimes also called antiepileptics, belong to a diverse group of pharmaceuticals used in prevention of the occurrence of epileptic seizures. ...

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Side-effects

At therapeutic doses, phenytoin produces horizontal gaze nystagmus, which is harmless but occasionally tested for by law enforcement as a marker for drunkenness (which can also produce nystagmus). At toxic doses, patients experience sedation, cerebellar ataxia, and ophthalmoparesis, as well as paradoxical seizures. Idiosyncratic side effects of phenytoin, as with other anticonvulsants, include rash and severe allergic reactions. Nystagmus is rapid involuntary rhythmic eye movement, with the eyes moving quickly in one direction (quick phase), and then slowly in the other (slow phase), there is also a twich in the eye(s) when this happens. ... For the band, see The Police. ... Drunkenness, in its most common usage, is the state of being intoxicated with ethyl alcohol to a sufficient degree to impair mental and motor functioning. ... Sedation is a medical procedure involving administration of sedative drugs, generally to facilitate a medical procedure, such as endoscopy, vasectomy, or minor surgery with local anaesthesia. ... Ataxia (from Greek ataxiā, meaning failure to put in order) is unsteady and clumsy motion of the limbs or trunk due to a failure of the gross coordination of muscle movements. ... Ophthalmoparesis is a physical finding in certain neurologic illnesses. ... This article is about the medical condition. ... The anticonvulsants, sometimes also called antiepileptics, belong to a diverse group of pharmaceuticals used in prevention of the occurrence of epileptic seizures. ... An allergy can refer to several kinds of immune reactions including Type I hypersensitivity in which a persons body is hypersensitised and develops IgE type antibodies to typical proteins. ...


There is some evidence that phenytoin is teratogenic, causing what Smith and Jones in their Recognizable Patterns of Human Malformation called the fetal hydantoin syndrome. There is some evidence against this. One blinded trial asked physicians to separate photographs of children into two piles based on whether they showed the so-called characteristic features of this syndrome; it found that physicians were no better at diagnosing the syndrome than would be expected by random chance, calling the very existence of the syndrome into question. Data now being collected by the Epilepsy and Antiepileptic Drug Pregnancy Registry may one day answer this question definitively. Teratogenesis is a medical term from the Greek, literally meaning monster-making, which derives from teratology, the study of the frequency, causation, and development of congenital malformations—misleadingly called birth defects. ...


Phenytoin may accumulate in the cerebral cortex over long periods of time, as well as causing atrophy of the cerebellum when administered at chronically high levels. Despite this, the drug has a long history of safe use, making it one of the more popular anti-convulsants prescribed by doctors, and a common "first line of defense" in seizure cases. Phenytoin also commonly causes gingival hypertrophy. Location of the cerebral cortex Slice of the cerebral cortex, ca. ... Figure 1a: A human brain, with the cerebellum in purple. ... The gingivae (sing. ... Bodybuilder Markus Rühl has marked hypertrophy of skeletal muscle. ...


Due to patent expiration, phenytoin is available in generic form and several branded forms at relatively low cost, making it one of the more affordable seizure control medications. It is available in extended release capsules and injectable forms, though the injectable formulation is rapidly losing ground to fosphenytoin. Some generic formulations of phenytoin have been felt to be less reliable with respect to time-release than their branded counterparts. In some cases, this can be related to complications which arise between the alternative protein bond release mechaninsms used in the generic versions, and those individuals with high metabolic rates. A patent is a set of exclusive rights granted by a state to a person for a fixed period of time in exchange for the regulated, public disclosure of certain details of a device, method, process or composition of matter (substance) (known as an invention) which is new, inventive, and... Look up Generic in Wiktionary, the free dictionary. ... Fosphenytoin (Cerebyx®, Parke-Davis) is a water-soluble phenytoin prodrug used in only in hospitals for the treatment of epileptic seizures. ...

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Legal issues

In 1995, Warner-Lambert, then producer of Dilantin, was fined $10 million after pleading guilty to charges that it hid quality control failures from regulators during the period 1990-1992. 1995 (MCMXCV) was a common year starting on Sunday of the Gregorian calendar. ... Pfizer, Incorporated (NYSE: PFE), is a global pharmaceutical company based in New York City. ... This article is about the year. ... 1992 (MCMXCII) was a leap year starting on Wednesday. ...

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See also

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Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound which can be thought of as a cyclic double-condensation reaction product of glycolic acid and urea. ... Fosphenytoin (Cerebyx®, Parke-Davis) is a water-soluble phenytoin prodrug used in only in hospitals for the treatment of epileptic seizures. ... Mephenytoin (marketed as Mesantoin® by Novartis) is a hydantoin, used as an anticonvulsant. ... Ethotoin (marketed as Peganone® by Ovation) is an anticonvulsant drug used in the treatment of epilepsy. ...

External links


This article is about the year. ... November 3 is the 307th day of the year (308th in leap years) in the Gregorian Calendar, with 58 days remaining. ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... September 5 is the 248th day of the year (249th in leap years). ...

Anticonvulsants (N03) edit

Barbiturates: Barbexaclone, Metharbital, Methylphenobarbital, Phenobarbital, Primidone The anticonvulsants, sometimes also called antiepileptics, belong to a diverse group of pharmaceuticals used in prevention of the occurrence of epileptic seizures. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Barbiturates are drugs that act as central nervous system (CNS) depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ... Barbexaclone (marketed in Italy as Maliasin by Abbott Laboratories). ... Metharbital was marketed as Gemonil by Abbott Laboratories. ... Methylphenobarbital (also known as mephobarbital) is marketed in the US as Mebaral by Ovation. ... Phenobarbital (also phenobarbitone) (Luminal®) is a weak acid with the chemical formula C12H12N2O3. ... Primidone, is an anticonvulsant of the pyrimidinedione class whose active metabolites, phenobarbital (minor) and phenylethylmalonamide (PEMA) (major), are also anticonvulsants. ...


Hydantoins: Ethotoin, Fosphenytoin, Mephenytoin, Phenytoin -- Oxazolidinediones: Ethadione, Paramethadione, Trimethadione Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound which can be thought of as a cyclic double-condensation reaction product of glycolic acid and urea. ... Ethotoin (marketed as Peganone® by Ovation) is an anticonvulsant drug used in the treatment of epilepsy. ... Fosphenytoin (Cerebyx®, Parke-Davis) is a water-soluble phenytoin prodrug used in only in hospitals for the treatment of epileptic seizures. ... Mephenytoin (marketed as Mesantoin® by Novartis) is a hydantoin, used as an anticonvulsant. ... The following are oxazolidinediones: paramethadione trimethadione ethadione Categories: Pharmacology stubs | Antiepileptics ... Ethadione is an anticonvulsant medication in the oxazolidinedione family. ... Paramethadione is an anticonvulsant in the oxazolidinedione class. ... Trimethadione is an oxazolidinedione anticonvulsant. ...


Succinimides: Ethosuximide, Mesuximide, Phensuximide Succinimides are drugs that can be used as anticonvulsants. ... Ethosuximide is a succinimide anticonvulsant, used mainly in absence seizures. ... Mesuximide (or methsuximide) is an anticonvulsant medication. ... Phensuximide is an anticonvulsant in the succinimide class. ...


Benzodiazepines: Clobazam, Clonazepam, Clorazepate, Diazepam, Lorazepam, Midazolam, Nitrazepam alprazolam 2mg tablets The benzodiazepines are a class of drugs with sedative, hypnotic, anxiolytic, anticonvulsant, amnestic and muscle relaxant properties. ... Clobazam is triazolobenzodiazepine, also known as a 1,5-benzodiazepine, meaning that its diazepine ring has its nitrogen atoms at the 1 and 5 positions instead of the usual 1 and 4. ... Clonazepam (marketed by Roche under the trade-name Klonopin® in the United States and Rivotril® in Europe, Brazil and Canada) is a drug which is a benzodiazepine derivative. ... Clorazepate (brand name: Tranxene®) is a member of the group of drugs called benzodiazepines. ... Diazepam (pronounced , marketed under brand names Valium, Stesolid, Seduxen Bosaurin and Apozepam)[1] is a drug which is a benzodiazepine derivative. ... Lorazepam (marketed under the brand names Ativan®, Temesta®, Tavor®) is a drug which is a benzodiazepine derivative. ... Midazolam, (marketed under brand names Versed®, Hypnovel® and Dormicum®) is a drug which is a benzodiazepine derivative. ... Nitrazepam (marketed under the trade names Mogadon®, Nitredon®, Nilandron®) is a powerful hypnotic drug, which is a benzodiazepine derivative. ...


Carboxamides: Carbamazepine, Oxcarbazepine, Rufinamide -- Fatty acid derivatives: Valpromide, Valnoctamide Carboxamides are drugs that can be used as anticonvulsants. ... Carbamazepine (sold under the brand-names Biston, Calepsin, Carbatrol, Epitol, Equetro, Finlepsin, Sirtal, Stazepine, Tegretol, Telesmin, Timonil) is an anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy and bipolar disorder. ... Oxcarbazepine (Marketed as Trileptal® by Novartis) is an anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy and bipolar disorder. ... Rufinamide is an anticonvulsant medication. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which either saturated or unsaturated. ... Valpromide (dipropylacetamide, α-propylvaleramide, Diprozin) is a carboxamide derivative of valproic acid that is considered safer to use than either valproic acid or sodium valproate. ... Valnoctamide has been used in France as a tranquilizer and muscle relaxant since 1964[3] and as an anticonvulsant since starting in 1969 in Portugal. ...


Carboxylic acids: Valproic acid (Sodium valproate & Valproate semisodium), Tiagabine -- GABA analogs: Gabapentin, Pregabalin, Progabide, Vigabatrin Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -(C=O)-OH, usually written as -COOH. In general, the salts and anions... Valproic acid or 2-Propylpentanoic acid is CH3CH2CH2CH(CH2CH2CH3)COOH . ... Sodium valproate (INN) or valproate sodium (USAN) is the sodium salt of valproic acid and is an anticonvulsant used in the treatment of epilepsy. ... Valproate semisodium (INN) or divalproex sodium (USAN) consists of a compound of sodium valproate and valproic acid in a 1:1 molar relationship in an enteric coated form. ... Tiagabine is an anti-convulsive medication produced by Cephalon and marketed under the brand name Gabitril. ... Gaba may refer to: Gabâ or gabaa (Philippines), the concept of negative karma of the Cebuano people GABA, the gamma-amino-butyric acid neurotransmitter GABA receptor, in biology, receptors with GABA as their endogenous ligand Gaba 1 to 1, an English conversational school in Japan Marianne Gaba, a US model... Gabapentin (brand name: Neurontin®) was initially synthesized to mimic the structure of GABA for the treatment of epilepsy. ... Pregabalin (brand name: Lyrica®) is a new anticonvulsant drug indicated as an add on therapy for partial onset seizures and for certain types of neuropathic pain. ... Progabide (INN) is an analog of gamma-aminobutyric acid used in the treatment of epilepsy. ... Vigabatrin is an anticonvulsant that inhibits the catabolism of GABA. It is an analog of GABA, but it is not a receptor agonist. ...


Others:- Monosaccharides: Topiramate -- Aromatic allylic alcohols: Stiripentol -- Ureas: Phenacemide, Pheneturide Monosaccharides are the simplest form of carbohydrates. ... Topiramate (brand name: Topamax®) is an anticonvulsant drug produced by Ortho-McNeil, a division of Johnson & Johnson. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... An allyl group is an alkene hydrocarbon group with the formula H2C=CH-CH2-. It is made up of a vinyl group, CH2=CH-, attached to a methylene -CH2. ... In chemistry, an alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. ... Stiripentol (marketed as Diacomit by Laboratoires BIOCODEX) is an anticonvulsant drug used in the treatment of epilepsy. ... Urea is an organic compound of carbon, nitrogen, oxygen and hydrogen, with the formula CON2H4 or (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Non-proprietary Names (rINN) in use in Europe. ... Phenacemide is an anticonvulsant of the urea class. ... Pheneturide (or ethylphenacemide) is an anticonvulsant medication. ...


Carbamates: Emylcamate, Felbamate, Meprobamate -- Pyrrolidines: Brivaracetam, Levetiracetam, Nefiracetam, Seletracetam Carbamates are a group of organic compounds sharing a common functional group with the general structure -NH(CO)O-. More precisely the carbamate group is considered an amide group with an alkoxy or hydroxy functional group next to the carbonyl group. ... Emylcamate (marketed as Striatran® by Merck) is an anxiolytic and muscle relaxant. ... Felbamate (marketed as Felbamol by MedPointe) is an anticonvulsant drug used in the treatment of epilepsy. ... Meprobamate (marketed under the brand names Miltown® by Wallace Laboratories and Equanil® by Wyeth) is a carbamate derivative which is used as an anxiolytic drug. ... Flash point 3 °C R/S statement R: 11 20/21/22 35 S: 16 26 28 36/37 45 RTECS number UX9650000 Related compounds Related compounds pyrrole piperidine Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and... Levetiracetam (brand name: Keppra®) is an anticonvulsant medication used to treat epilepsy. ... Categories: Stub | Substances of the piracetam group ...


Sulfa drugs: Acetazolamide, Ethoxzolamide, Sultiame, Zonisamide -- Propionates: Beclamide -- Aldehydes: Paraldehyde -- Bromides: Potassium bromide There are several sulphonamide-based groups of drugs. ... Acetazolamide, sold under the trade name Diamox®, is a carbonic anhydrase inhibitor that is used to treat glaucoma, epileptic seizures, benign intracranial hypertension and altitude sickness. ... Ethoxzolamide (6-ethoxybenzothiazole-2-sulfonamide, alternatively known as Ethoxyzolamide) is a sulfonamide medication that functions as a carbonic anhydrase inhibitor. ... Sulthiame (or Sultiame) is an anticonvulsant drug. ... Zonisamide (brand name Zonegran®) is an anticonvulsant used as an adjunctive therapy in adults with partial-onset seizures. ... The propionate (also propanoate) ion is C2H5COO− (propionic acid minus one hydrogen ion). ... Beclamide (marketed as Chloracon, Hibicon, Posedrine, Nydrane, Seclar, and other names) is a propionate and was used as a sedative and as an anticonvulsant. ... An aldehyde. ... Paraldehyde is the cyclic form of three acetaldehyde molecules (a trimer). ... A bromide is a phrase, or person who uses phrases, which have been used and repeated so many times as to become either insincere in their meaning, or seem like an attempt at trying to explain the obvious. ... Potassium bromide (KBr) is a salt, used as an anticonvulsant and a sedative in the 1800s. ...


  Results from FactBites:
 
Phenytoin - Wikipedia, the free encyclopedia (661 words)
Phenytoin sodium (marketed as Dilantin® in the USA and as Epanutin® in the UK, by Parke-Davis, now part of Pfizer) is a commonly used antiepileptic.
Phenytoin acts to damp the unwanted, runaway brain activity seen in seizure by reducing electrical conductance among brain cells.
Phenytoin may accumulate in the cerebral cortex over long periods of time, as well as causing atrophy of the cerebellum when administered at chronically high levels.
  More results at FactBites »

 
 

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