Fosphenytoin sodium

Bezeichnung:Fosphenytoin sodium

CAS-Nr92134-98-0

Englisch Name:Fosphenytoin sodium

CBNumberCB4692780

SummenformelC16H16N2NaO6P

Molgewicht386.28

MOL-Datei92134-98-0.mol

Fosphenytoin sodium physikalisch-chemischer Eigenschaften

Schmelzpunkt	220° (softens)
storage temp.	Inert atmosphere,2-8°C
Löslichkeit	H2O: ≥15mg/mL
Aggregatzustand	powder
Farbe	white to tan

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	45-61-22
S-Sätze:	53-36/37-45
RIDADR	UN 2811 6.1 / PGIII
WGK Germany	3
HS Code	2933290000
Toxizität	LD50 in mice, rats (mg/kg): 234, 363 i.v. (Smith)

Gefahreninformationscode (GHS)

Fosphenytoin sodium Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Cerebyx,Pfizer
Verwenden
Anti epileptic
Verwenden
PDE3 (phosphodiesterase 3) inhibitor
Verwenden
Fosphenytoin sodium is used in the treatment of epileptic seizures.
Manufacturing Process
By action of formaldehyde and hydrochloric acid on 5,5-diphenylhydantoin was prepared 3-hydroxymethyl-5,5-diphenyl-imidazolidine-2,4-dione which was converted by action PCl3 to 3-chloromethyl-5,5-diphenyl-imidazolidine-2,4- dione by action PCl3. Then the chlorine atom was substituted on P(O)(OBz)Ogroup by action of argentum salt of phosphoric acid dibenzyl ester. Removal of the protecting groups by hydrogenolysis gives the 2,4-imidazolidinedione, 5,5- diphenyl-3-((phosphonooxy)methyl)- (fosphenytoin).
In practice it is usually used as sodium salt.
Trademarks
Cerebyx (Parke-Davis).
Therapeutic Function
Antiepileptic, Anticonvulsant
Clinical Use
Control of status epilepticus
Seizures associated with neurosurgery or head injury when oral phenytoin is not possible
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs Aminophylline and theophylline: concentration of both drugs reduced with aminophylline and theophylline. Analgesics: enhanced effect with NSAIDs; metabolism of methadone accelerated; possibly increases pethidine toxicity. Anthelmintics: concentration of albendazole and praziquantel reduced; concentration of fosphenytoin possibly increased by levamisole. Anti-arrhythmics: increased concentration with amiodarone; concentration of disopyramide and possibly dronedarone reduced - avoid with dronedarone. Antibacterials: level increased by clarithromycin, chloramphenicol, isoniazid, metronidazole, sulphonamides and trimethoprim (+ antifolate effect); concentration increased or decreased by ciprofloxacin; concentration of bedaquiline, doxycycline and telithromycin reduced - avoid with telithromycin; concentration reduced by rifamycins.
Anticoagulants: increased metabolism of coumarins (reduced effect but also reports of enhancement); possibly reduced apixaban, dabigatran, edoxaban and rivaroxaban concentration - avoid with dabigatran.
Antidepressants: antagonise anticonvulsant effect; concentration increased by fluoxetine and fluvoxamine and possibly sertraline; concentration of mianserin, mirtazapine and paroxetine and possibly tricyclics reduced; concentration reduced by St John’s wort - avoid.
Antiepileptics: concentration of both drugs reduced with carbamazepine, concentration may also be increased by carbamazepine, eslicarbazepine, ethosuximide, oxcarbazepine, stripentol and topiramate; concentration of ethosuximide, active oxcarbazepine metabolite, retigabine, rufinamide (concentration of phenytoin possibly increased), topiramate and valproate possibly reduced; concentration of eslicarbazepine, ethosuximide, lamotrigine, perampanel, tiagabine and zonisamide reduced; concentration of phenobarbital often
increased; phenobarbital and valproate may alter concentration; concentration reduced by vigabatrin.
Antifungals: concentration of ketoconazole, itraconazole, posaconazole, voriconazole and possibly isavuconazole and caspofungin reduced - avoid with isavuconazole and itraconazole, increase voriconazole dose and possibly caspofungin; levels increased by fluconazole, miconazole and voriconazole - consider reducing fosphenytoin dose.
Antimalarials: avoid with piperaquine with artenimol, mefloquine and pyrimethamine - antagonise anticonvulsant effect; increased antifolate effect with pyrimethamine.
Antipsychotics: antagonise anticonvulsant effect; possibly reduced aripiprazole concentration - increase aripiprazole dose; metabolism of clozapine, haloperidol, quetiapine and sertindole increased; concentration increased or decreased with chlorpromazine; possibly reduces lurasidone concentration - avoid.
Antivirals: possibly reduced concentration of abacavir, boceprevir, daclatasvir, darunavir, dasabuvir, dolutegravir, indinavir, lopinavir, ombitasvir, paritaprevir, ritonavir, saquinavir and simeprevir - avoid with boceprevir, daclatasvir, dasabuvir, ombitasvir, paritaprevir and simeprevir; rilpivirine reduced - avoid; concentration possibly increased by indinavir and ritonavir; concentration increased or decreased with zidovudine; avoid with elvitegravir,
etravirine and telaprevir.
Apremilast: concentration of apremilast reduced - avoid.
Calcium-channel blockers: levels increased by diltiazem; concentration of diltiazem, felodipine, isradipine, nimodipine and verapamil reduced; avoid with isradipine and nimodipine.
Cannabis extract: concentration possibly reduced by phenytoin - avoid.
Ciclosporin: reduced ciclosporin levels.
Cobicistat: concentration of cobicistat possibly reduced.
Corticosteroids: metabolism accelerated (effect reduced)
. Cytotoxics: metabolism possibly inhibited by
fluorouracil; increased antifolate effect with methotrexate; reduced fosphenytoin absorption; concentrat
Stoffwechsel
Fosphenytoin is rapidly and completely hydrolysed to phenytoin with a conversion half-life of about 15 minutes; one mmol of fosphenytoin yields one mmol of phenytoin. Phenytoin is hydroxylated in the liver to inactive metabolites chiefly 5-(4-hydroxyphenyl)-5- phenylhydantoin by an enzyme system which is saturable. Phenytoin undergoes enterohepatic recycling and is excreted in the urine, mainly as its hydroxylated metabolite, in either free or conjugated form.

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