Tamiflu.
Tamiflu is a modern antiviral drug lincenced for the treatment
of influenza within the first 48hours of symptoms appearing. Tamiflu or
oseltamivir phosphate is manufactured as 75mg oral tablets by Roch
pharmaceuticals. The chemical structure is shown bellow:
Oseltamivir
phosphate is a prodrug which requires metabolism into the active molecule in
this case the carboxylate of the molecule shown, this can be achieved by
esterification by enzymes found primarily in the liver. The mechanism of action
will be discussed in the next section. Currently the product licence belongs
to Roch pharmaceuticals. Roch are the sole manufactures of the drug to date,
Although if in the case of a serious influenza pandemic the world health
organisation can opt to lift this licence allowing other companies to produce
the drug (Such a move has never before been invoked but in the light of the
limited supply of tamiflu and the outbreak of avian bird flu such a move could be
taken in the future.) The limited supply of Tamiflu is due to the difficulty of
the synthesis of this drug, The current method used involves explosive azides as
intermediates in two of the steps, also the starting materials are not readily
available and cost of manufacture is high. This limited supply has lead many
countries and in some cases individuals to start stockpiling the drug for
emergency use.
The current synthesis is shown systematically bellow:
Alternative methods of production have been proposed recently,
but very little information is currently available.
Click on the images below to view the interactive 3D structure of Tamiflu.
Oseltamivir
phosphate is a prodrug which requires metabolism into the active molecule in
this case the carboxylate of the molecule shown, this can be achieved by
esterification by enzymes found primarily in the liver. The mechanism of action
will be discussed in the next section. Currently the product licence belongs
to Roch pharmaceuticals. Roch are the sole manufactures of the drug to date,
Although if in the case of a serious influenza pandemic the world health
organisation can opt to lift this licence allowing other companies to produce
the drug (Such a move has never before been invoked but in the light of the
limited supply of tamiflu and the outbreak of avian bird flu such a move could be
taken in the future.) The limited supply of Tamiflu is due to the difficulty of
the synthesis of this drug, The current method used involves explosive azides as
intermediates in two of the steps, also the starting materials are not readily
available and cost of manufacture is high. This limited supply has lead many
countries and in some cases individuals to start stockpiling the drug for
emergency use.