Analgesics: From Chemistry and Pharmacology to Clinical by by Helmut Buschmann (Editor), Thomas Christoph (Editor),

By by Helmut Buschmann (Editor), Thomas Christoph (Editor), Elmar Friderichs (Editor), Corinna Maul (Ed

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1991). Etodolac is a racemate with an active (S)enantiomer and an inactive (R)-enantiomer. Etodolac shows efficacy in a wide variety of diverse pain states. It is used for the treatment of mild to moderate acute and chronic pain including rheumatoid arthritis and osteoarthritis. Etodolac is administered orally (400-1200 mg/day). Peak plasma concentrations are reached within 2 h. Etodolac shows 99 % binding to plasma protein and an elimination half-life of about 7 h (Brooks and Jamali, 1994). Etodolac is metabolized almost completely to the main metabolites 6- or 7-hydroxy-etodolac, acylglucuronide, 8-(1 '-hydroxyethyl)-etodolac and 4-ureidoetodolac.

G. , 1996). , 1998). Aspirin and APHS acetylate the amino acid serine so that endogenic arachidonic acid is prevented from reaching the catalytic center of the enzymes. _ .. A A , - _w . • Reversible, competitive inhibitors of COX-1 and COX-2. Inhibitors such as ibuprofen, piroxicam or mefenamic acid compete against arachidonic acid to bind at the catalytic center. • Slow, time-dependent, reversible inhibitors of COX1 and COX-2. g. indomethacin and flurbiprofen seem to act by ionic interactions between their carboxylic acid function and the arginine residue of the enzyme.

2000). 022 ^iM COX-1: IC50 = 30 nM COX-1: I Figure 11: Modification of diclofenac. f 1995). An Increase in selectivity was achieved by replacing the oxygen with a methylene group at the 4-position of the pyran ring, by transformation of the ketone into an oxime or by complete reduction of the pyran ring (Failli et al. (American Home Products), 1998b; Kreft et al. , 2000). 7 ^M COX-1: IC50 COX-1: IC50 = 23 |uM Figure 12: Modification of etodolac. , 1999, (Merck Frosst), 1999). Optimal selectivity was conferred by a 3-atom lipophilic substitution at the 3' position of the unsubstituted phenyl ring.

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