Description
Mofezolac is a new non-steroidal analgesic antiinflammatory agent introduced in
Japan for the treatment of post-operative and post-traumatic pain, acute upper
respiratory tract pain, osteoarthritis, and lumbago. In in vfim studies, mofezolac
inhibits prostaglandin biosynthesis and platelet aggregation, reportedly through the
inhibition of cyclooxygenase. In animal studies, mofezolac showed more potent
suppression in various writhing models than agents such as ibuprofen, mefenamic
acid and aspirin. Mofezolac also has a potent inhibitory activity on the algesic
responses induced by the mechanical stimulus of the inflamed tissue. The
ulcerogenic effect of mofezolac on the gastric mucosa is far weaker than that of
indomethacin and other agents.
Originator
Pasteur Merieux (France)
Definition
ChEBI: Mofezolac (TN) is a member of methoxybenzenes.
Clinical Use
Yoshitomi (now Mitsubishi
Pharma) has launched mofezolac, a COX-1 inhibitor
with preferential COX-1 inhibition
for the treatment of arthritis-related pain
in Japan.
The compound is used in oral doses of 75mg
for the treatment of periarthritis, lumbago, neckshoulder-
arm syndrome and pain after surgery,
trauma, or dental extraction.
Synthesis
The reaction of deoxyanisoin with hydroxylamine
in methanol gives the corresponding
1,2-bis(4-methoxyphenyl)ethanone oxime,
which is cyclized with ethyl acetate by means
of n-butyllithium in tetrahydrofuran yielding
3,4-di(4-methoxyphenyl)-5-methylisoxazole.
Finally, this compound is condensed
with CO2 with n-butyllithium as catalyst
in tetrahydrofuran to yield mofezolac . The synthesis with ClCO2C2H5 instead
of CO2 is described in .
