Cerebyx was launched for the treatment of status epilepticus and
for neurosurgery derived seizures. Fosphenytoin is rapidly converted by
phosphatases to phenytoin. This compound is readily water soluble thus overcoming
an important problem associated with Dilantin.
Originator
Warner-Lambert (USA)
Uses
Anticonvulsant.
Definition
ChEBI: Fosphenytoin is an imidazolidine-2,4-dione.
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.
