Mofezolac Chemical Properties

Melting point:

147.5℃

Boiling point:

527.2±50.0 °C(Predicted)

Density 

1.250±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble

form 

A solid

pka

pKa ~3.3(at 25℃)

color 

White to off-white

Safety Information

Toxicity

LD50 in male, female mice, male, female rats (mg/kg): 1528, 1740, 920, 887 orally; 275, 321, 378, 342 i.p.; 612, 545, 572, 510 s.c. (Satoh)

Mofezolac Usage And Synthesis

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.

brand name

Disopain

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 .

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