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Namespace Prefixes

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Statements

Subject Item
n2:DB01320
rdf:type
n6:Drug
n6:description
Fosphenytoin is a water-soluble phenytoin prodrug used only in hospitals for the treatment of epileptic seizures. It works by slowing down impulses in the brain that cause seizures. Its main mechanism is to block frequency-dependent, use-dependent and voltage-dependent neuronal sodium channels, and therefore limit repetitive firing of action potentials.
n6:dosage
n18:271B64E4-363D-11E5-9242-09173F13E4C5 n18:271B64E5-363D-11E5-9242-09173F13E4C5 n18:271B64E2-363D-11E5-9242-09173F13E4C5 n18:271B64E3-363D-11E5-9242-09173F13E4C5
n6:generalReferences
# Johnson J, Wrenn K: Inappropriate fosphenytoin use in the ED. Am J Emerg Med. 2001 Jul;19(4):293-4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11447516 # Applebaum J, Levine J, Belmaker RH: Intravenous fosphenytoin in acute mania. J Clin Psychiatry. 2003 Apr;64(4):408-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12716241 # McCleane GJ: Intravenous infusion of fosphenytoin produces prolonged pain relief: a case report. J Pain. 2002 Apr;3(2):156-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/14622802 # Browne TR, Kugler AR, Eldon MA: Pharmacology and pharmacokinetics of fosphenytoin. Neurology. 1996 Jun;46(6 Suppl 1):S3-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/ 8649612 # Luszczki JJ: Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. Pharmacol Rep. 2009 Mar-Apr;61(2):197-216. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19443931
n6:group
approved
n6:halfLife
Fosphenytoin has a half-life of approximately 15 minutes.
n6:indication
For the control of generalized convulsive status epilepticus and prevention and treatment of seizures occurring during neurosurgery. It can also be substituted, short-term, for oral phenytoin.
owl:sameAs
n13:DB01320 n23:DB01320
dcterms:title
Fosphenytoin
adms:identifier
n4:56339 n5:C07840 n8:0071-4007-05 n9:46505168 n24:DB01320 n26:PA164746820 n27:50839 n28:Fosphenytoin
n6:mechanismOfAction
Fosphenytoin is a prodrug of phenytoin and accordingly, its anticonvulsant effects are attributable to phenytoin. Phenytoin acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. By promoting sodium efflux from neurons, phenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of post-tetanic potentiation at synapses. Loss of post-tetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas.
n6:packager
n14:271B64DE-363D-11E5-9242-09173F13E4C5 n14:271B64DF-363D-11E5-9242-09173F13E4C5 n14:271B64DC-363D-11E5-9242-09173F13E4C5 n14:271B64DD-363D-11E5-9242-09173F13E4C5 n14:271B64DA-363D-11E5-9242-09173F13E4C5 n14:271B64DB-363D-11E5-9242-09173F13E4C5 n14:271B64D8-363D-11E5-9242-09173F13E4C5 n14:271B64D9-363D-11E5-9242-09173F13E4C5 n14:271B64D6-363D-11E5-9242-09173F13E4C5 n14:271B64D7-363D-11E5-9242-09173F13E4C5 n14:271B64D4-363D-11E5-9242-09173F13E4C5 n14:271B64D5-363D-11E5-9242-09173F13E4C5 n14:271B64D2-363D-11E5-9242-09173F13E4C5 n14:271B64D3-363D-11E5-9242-09173F13E4C5 n14:271B64D0-363D-11E5-9242-09173F13E4C5 n14:271B64D1-363D-11E5-9242-09173F13E4C5
n6:routeOfElimination
Phenytoin derived from administration of Cerebyx is extensively metabolized in the liver and excreted in urine primarily as 5-(p-hydroxyphenyl)-5-phenylhydantoin and its glucuronide; little unchanged phenytoin (1%–5% of the Cerebyx dose) is recovered in urine.
n6:synonym
(3-Phosphoryloxymethyl)phenytoin Fosphenytoine Fosphenytoin Fosfenitoina Fosphenytoinum Cerebyx
n6:toxicity
Nausea, vomiting, lethargy, tachycardia, bradycardia, asystole, cardiac arrest, hypotension, syncope, hypocalcemia, metabolic acidosis, and death have been reported in cases of overdosage with fosphenytoin. The median lethal dose of fosphenytoin given intravenously in mice and rats was 156 mg PE/kg and approximately 250 mg PE/kg, or about 0.6 and 2 times, respectively, the maximum human loading dose on a mg/m2 basis. Signs of acute toxicity in animals included ataxia, labored breathing, ptosis, and hypoactivity.
n6:volumeOfDistribution
* 4.3 to 10.8 L
n20:hasAHFSCode
n22:28-12-12
n6:foodInteraction
Take with food. Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication. Avoid alcohol.
n6:proteinBinding
Extensively bound (95% to 99%) to human plasma proteins, primarily albumin.
n6:salt
n6:synthesisReference
Volker Kirsch, "Process for the preparation of sodium fosphenytoin." U.S. Patent US20050272706, issued December 08, 2005.
n16:hasConcept
n17:M0127036
foaf:page
n11:fosphen.htm n25:fosphenytoin.html
n6:IUPAC-Name
n7:271B64EA-363D-11E5-9242-09173F13E4C5
n6:InChI
n7:271B64F0-363D-11E5-9242-09173F13E4C5
n6:Molecular-Formula
n7:271B64EF-363D-11E5-9242-09173F13E4C5
n6:Molecular-Weight
n7:271B64EC-363D-11E5-9242-09173F13E4C5
n6:Monoisotopic-Weight
n7:271B64ED-363D-11E5-9242-09173F13E4C5
n6:SMILES
n7:271B64EE-363D-11E5-9242-09173F13E4C5
n6:Water-Solubility
n7:271B64E8-363D-11E5-9242-09173F13E4C5
n6:logP
n7:271B64E6-363D-11E5-9242-09173F13E4C5 n7:271B64E9-363D-11E5-9242-09173F13E4C5
n6:logS
n7:271B64E7-363D-11E5-9242-09173F13E4C5
n20:hasATCCode
n21:N03AB05
n6:H-Bond-Acceptor-Count
n7:271B64F6-363D-11E5-9242-09173F13E4C5
n6:H-Bond-Donor-Count
n7:271B64F7-363D-11E5-9242-09173F13E4C5
n6:InChIKey
n7:271B64F1-363D-11E5-9242-09173F13E4C5
n6:Polar-Surface-Area--PSA-
n7:271B64F2-363D-11E5-9242-09173F13E4C5
n6:Polarizability
n7:271B64F4-363D-11E5-9242-09173F13E4C5
n6:Refractivity
n7:271B64F3-363D-11E5-9242-09173F13E4C5
n6:Rotatable-Bond-Count
n7:271B64F5-363D-11E5-9242-09173F13E4C5
n6:absorption
Fosphenytoin is completely bioavailable following lM administration.
n6:affectedOrganism
Humans and other mammals
n6:casRegistryNumber
93390-81-9
n6:category
n6:containedIn
n15:271B64E0-363D-11E5-9242-09173F13E4C5 n15:271B64E1-363D-11E5-9242-09173F13E4C5
n6:Bioavailability
n7:271B64FC-363D-11E5-9242-09173F13E4C5
n6:Ghose-Filter
n7:271B64FE-363D-11E5-9242-09173F13E4C5
n6:MDDR-Like-Rule
n7:271B64FF-363D-11E5-9242-09173F13E4C5
n6:Number-of-Rings
n7:271B64FB-363D-11E5-9242-09173F13E4C5
n6:Physiological-Charge
n7:271B64FA-363D-11E5-9242-09173F13E4C5
n6:Rule-of-Five
n7:271B64FD-363D-11E5-9242-09173F13E4C5
n6:Traditional-IUPAC-Name
n7:271B64EB-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-acidic-
n7:271B64F8-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-basic-
n7:271B64F9-363D-11E5-9242-09173F13E4C5