n.
A prodrug that is metabolized to phenytoin and administered parenterally for the treatment of seizures.
[Alteration of PHOS(PHORUS) + PHENYTOIN.]
fosphenytoin
| Dictionary: fos·phen·y·to·in |
(fŏs'fĕn'ĭ-tō'ĭn, -fə-nĭt'ō-)
n.
A prodrug that is metabolized to phenytoin and administered parenterally for the treatment of seizures.
n.
A prodrug that is metabolized to phenytoin and administered parenterally for the treatment of seizures.
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| Drug Info: Fosphenytoin |
Brand names: Cerebyx®
Chemical formula:
- Drug Forms:
- Fosphenytoin injection (below)
- Fosphenytoin Sodium Solution for injection
Fosphenytoin injection
What is fosphenytoin injection?
FOSPHENYTOIN (Cerebyx®) helps to control seizures (convulsions) in certain types of epilepsy. Fosphenytoin can help to prevent seizures occurring during or after surgery. Generic fosphenytoin injections are not available.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
• an alcohol abuse problem
• blood disorders or disease
• depression
• diabetes
• fever
• heart problems, low blood pressure
• kidney disease
• liver disease
• porphyria
• receiving intramuscular injections
• receiving radiation therapy
• skin problems
• suicidal thoughts, plans, or attempt; a previous suicide attempt by you or a family member
• thyroid disease
• an unusual or allergic reaction to phenytoin, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I use this medicine?
Fosphenytoin is for injection into a vein or muscle or for infusion into a vein. It is given by a health-care professional in a hospital or clinic setting.
What if I miss a dose?
This does not apply. Your condition will be closely monitored to maintain adequate seizure control.What drug(s) may interact with fosphenytoin?
Many medicines can interact with fosphenytoin; check with your prescriber or health care professional if you regularly take other medications or over-the-counter products. Some of the medicines that can interact with fosphenytoin are listed:
• alcohol
• amphetamines
• aspirin and aspirin-like medicines
• barbiturate medicines for inducing sleep or treating seizures (convulsions)
• bosentan
• carbamazepine
• cimetidine
• ciprofloxacin
• clopidogrel
• cyclosporine
• disulfiram
• ethosuximide
• felbamate
• female hormones, including contraceptive or birth control pills
• fluconazole
• folic acid, vitamin B9
• heart medicines such as digoxin or digitoxin
• chloramphenicol
• corticosteroid hormones such as prednisone or cortisone
• isoniazid
• itraconazole
• kava kava
• ketoconazole
• leucovorin
• levodopa
• lidocaine
• medicines for diabetes
• medicines for hay fever and other allergies
• medicines for mental depression, anxiety or other mood problems
• medicines to control heart rhythm
• medicines used to treat HIV infection or AIDS
• methadone or other medicines for pain
• methsuximide
• modafinil
• omeprazole
• oxcarbazepine
• rifampin, rifabutin or rifapentine
• sirolimus
• St. John's wort
• tacrolimus
• theophylline
• tiagabine
• ticlopidine
• tramadol
• valproic acid
• voriconazole
• warfarin
• zonisamide
Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking fosphenytoin?
Visit your prescriber or health care professional for regular checks on your progress. Your prescriber or health care professional may schedule regular blood tests. Do not stop using fosphenytoin suddenly; this increases the risk of seizures. Because your condition and the use of fosphenytoin carry some risk, it is a good idea to carry an identification card, necklace or bracelet with details of your condition, medications and prescriber or health care professional.
You may feel dizzy or drowsy. Do not drive, use machinery, or do anything that needs mental alertness until you know how fosphenytoin affects you. To reduce the risk of dizzy or fainting spells, do not sit or stand up quickly, especially if you are an older patient. Alcohol can make you more dizzy, increase flushing and may cause rapid heartbeats. Avoid alcoholic drinks while receiving fosphenytoin.
The use of this medicine may increase the chance of suicidal thoughts or actions. Pay special attention to how you are responding while on this medicine. Any worsening of mood, or thoughts of suicide or dying should be reported to your health care professional right away.
Fosphenytoin can cause unusual growth of gum tissues; visit your dentist regularly. Problems can arise if you need dental work, and in the day to day care of your teeth. Try to avoid damage to your teeth and gums when you brush or floss your teeth.
What side effects may I notice from receiving fosphenytoin?
Side effects that you should report to your prescriber or health care professional as soon as possible:
• confusion, nervousness, hostility, or other behavioral changes (especially in children or elderly patients)
• difficulty breathing, wheezing or shortness of breath
• double vision or uncontrollable and rapid eye movement
• fever, sore throat
• headache
• loss of seizure control
• mouth ulcers
• pain, redness, swelling or irritation at the injection site
• poor control of body movements or difficulty walking
• sexual problems (painful erections, loss of sexual desire)
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• skin rash, itching
• stomach pain
• swollen or painful glands
• unusual bleeding or bruising, pinpoint red spots on skin
• unusual tiredness or weakness
• unusual swelling
• worsening of mood, thoughts or actions of suicide or dying
• yellowing of the eyes or skin
Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• clumsiness or unsteadiness
• constipation
• difficulty sleeping
• dizziness or drowsiness
• dry mouth
• excessive hair growth on the face or body
• nausea, vomiting
• unusual growth of gum tissue
Where can I keep my medicine?
Keep out of the reach of children.
Store in a refrigerator between 2 and 8 degrees C (36 and 46 degrees F); do not freeze. Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
| Wikipedia: Fosphenytoin |
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Fosphenytoin
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| Systematic (IUPAC) name | |
| (2,5-dioxo-4,4-diphenyl-imidazolidin-1-yl)methoxyphosphonic acid | |
| Identifiers | |
| CAS number | |
| ATC code | N03 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C16H15N2O6P |
| Mol. mass | 362.274 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 100% (IM) |
| Protein binding | 95 to 99% |
| Metabolism | Hepatic |
| Half life | 15 minutes to convert to phenytoin |
| Excretion | Renal (as phenytoin) |
| Therapeutic considerations | |
| Pregnancy cat. |
D(US) |
| Legal status |
℞ Prescription only |
| Routes | Intravenous, intramuscular |
Fosphenytoin (Cerebyx, Parke-Davis; Prodilantin, Pfizer Holding France[1]) is a water-soluble phenytoin prodrug used only in hospitals for the treatment of epileptic seizures.
On 18 November 2004, Sicor (a subsidiary of Teva) received a tentative approval letter from the United States Food and Drug Administration for a generic version of fosphenytoin.[2]
Contents |
Uses
Approved
Fosphenytoin is approved in the United States for the short term (five days or less) treatment of epilepsy when more widely used means of phenytoin administration are not possible or are ill-advised,[3] such as endotracheal intubation, status epilepticus or some other type of repeated seizures; vomiting, and/or the patient is unalert or not awake or both.[4]
Unapproved/off-label/investigational
In April 2003, Applebaum and colleagues at the Ben-Gurion University of the Negev in Beersheba reported that even though anticonvulsants are often very effective in mania, and acute mania requires rapid treatment, fosphenytoin had no antimanic effect even 60 minutes after administration of doses used in status epilepticus.[5]
Fosphenytoin was more successfully used to relieve pain refractory to opiates in a 37-year-old woman with neuroma, according to Dr. Gary J. McCleane of the Rampark Pain Center in Lurgan, Northern Ireland.[6] She was given 1,500 phenytoin equivalent units of fosphenytoin over a 24 hour period, producing pain relief that last three to fourteen weeks after each infusion, allowing her to use less opiates.[6]
Metabolism
One mmol (millimole) of phenytoin is produced for every mmol of fosphenytoin administered; the hydrolysis of fosphenytoin also yields phosphate and formaldehyde, the latter of which is subsequently metabolized to formate, which is in turn metabolized by a folate dependent mechanism.[3]
Side effects
Side effects are similar to phenytoin, except that fosphenytoin causes less hypotension and more paresthesia.[7] Fosphenytoin can cause hyperphosphatemia in end-stage renal failure patients.[8]
History
Phenytoin, in both its acidic and sodium salt forms, is erratically bioavailable whether it is injected or taken orally due to its high melting point, weak acidity, and its being only sparingly soluble in water.[9] Simply putting patients on other drugs is not always an option; this was especially true before 1993, when the number of anticonvulsants available was much more limited.[10] One solution was to develop a prodrug that did not have these drawbacks.
Fosphenytoin was approved by the Food and Drug Administration (FDA) on August 5, 1996 for use in epilepsy.[11]
References
- ^ "PRODILANTIN 75 mg/ml sol inj IM et p perf IV". VIDAL, l'information de référence sur les produits de santé. http://www.vidal.fr/Medicament/prodilantin-13783.htm. Retrieved on 23 October 2005.
- ^ "Fosphenytoin Sodium Approval History". http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Label_ApprovalHistory#apphist. Retrieved on 20 October 2005.
- ^ a b Parke-Davis (2001). "Cerebyx: Fosphenytoin Sodium Injection - Labeling Revision" (PDF). Cerebyx Approval History. Warner-Lambert Company. http://www.fda.gov/cder/foi/label/2001/20450s4s5lbl.pdf. Retrieved on 20 October 2005.
- ^ Johnson J, Wrenn K (2001). "Inappropriate fosphenytoin use in the ED". American Journal of Emergency Medicine 19 (4): 293–4. doi:. PMID 11447516. Fulltext options List of Library Holdings Worldwide
- ^ Applebaum J, Levine J, Belmaker RH (2003). "Intravenous fosphenytoin in acute mania" (PDF). Journal Clinical Psychiatry 64 (4): 408–9. PMID 12716241. http://www.psychiatrist.com/privatepdf/2003/v64n04/v64n0408.pdf.
- ^ a b McCleane GJ (2002). "Intravenous infusion of fosphenytoin produces prolonged pain relief: a case report". The Journal of Pain 3 (2): 156–8. doi:. PMID 14622802. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=14622802&dopt=ExternalLink. List of Library Holdings Worldwide
- ^ Browne TR. (1997). "Fosphenytoin (Cerebyx)". Clinical Neuropharmacology 20 (1): 1–12. doi:. PMID 9037568. List of Library Holdings Worldwide
- ^ McBryde KD, Wilcox J, Kher KK (2005). "Hyperphosphatemia due to fosphenytoin in a pediatric ESRD patient" (PDF). Pediatric Nephrology (Berlin, Germany) 20 (8): 1182–5. doi:. PMID 15965770. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=15965770&dopt=ExternalLink.
- ^ Yamaoka Y, Roberts RD, Stella VJ (April 1983). "Low-melting phenytoin prodrugs as alternative oral delivery modes for phenytoin: a model for other high-melting sparingly water-soluble drugs". J Pharm Sci 72 (4): 400–5. PMID 6864479.
- ^ Anticonvulsants before 1993 Neuroland
- ^ "Cerebyx Approval History". http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Label_ApprovalHistory. Retrieved on 20 October 2005.
See also
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