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Synthesis and pharmacological evaluation of 1-methyl-5-[substituted-4 (3H)-oxo-1,2,3-benzotriazin-3-yl]-1H-pyrazole-4-acetic acid derivatives. 1998

G Daidone, and B Maggio, and S Plescia, and D Raffa, and D Schillaci, and O Migliara, and A Caruso, and V M Cutuli, and M Amico-Roxas
Dipartimento di Chimica e Tecnologie Farmaceutiche, Università degli Studi di Palermo, Italy.

Several new 1-methyl-5-[substituted-4-oxo-1,2,3-benzotriazin-3-yl] -1H-pyrazole-4-acetic acids and their ethyl ester derivatives were prepared. The compounds were tested for analgesic and antiinflammatory activities, acute toxicity, ulcerogenic effect, and as in vitro inhibitors of 3 alpha-hydroxysteroid dehydrogenase (3 alpha-HSD), since it is claimed that the inhibition of such an enzyme predicts in vivo antiinflammatory activity. Some compounds were more active than phenylbutazone in the phenylbenzoquinone and acetic acid peritonitis tests, and equiactive to the same drug in the carrageenin paw edema test. All the compounds inhibited the 3 alpha-HSD, but no correlation was observed with the paw edema inhibition values. The compounds proved to possess marginal or no ulcerogenic effect, as well as low systemic toxicity.

UI MeSH Term Description Entries
D008297 Male Males
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D000700 Analgesics Compounds capable of relieving pain without the loss of CONSCIOUSNESS. Analgesic,Anodynes,Antinociceptive Agents,Analgesic Agents,Analgesic Drugs,Agents, Analgesic,Agents, Antinociceptive,Drugs, Analgesic
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000893 Anti-Inflammatory Agents Substances that reduce or suppress INFLAMMATION. Anti-Inflammatory Agent,Antiinflammatory Agent,Agents, Anti-Inflammatory,Agents, Antiinflammatory,Anti-Inflammatories,Antiinflammatories,Antiinflammatory Agents,Agent, Anti-Inflammatory,Agent, Antiinflammatory,Agents, Anti Inflammatory,Anti Inflammatories,Anti Inflammatory Agent,Anti Inflammatory Agents
D015096 3-Hydroxysteroid Dehydrogenases Catalyze the oxidation of 3-hydroxysteroids to 3-ketosteroids. 3-beta-Hydroxysteroid Dehydrogenase,3 Hydroxysteroid Dehydrogenases,3 beta Hydroxysteroid Dehydrogenase,Dehydrogenase, 3-beta-Hydroxysteroid,Dehydrogenases, 3 Hydroxysteroid,Dehydrogenases, 3-Hydroxysteroid,Hydroxysteroid Dehydrogenases, 3
D045002 3-alpha-Hydroxysteroid Dehydrogenase (B-Specific) A 3-hydroxysteroid dehydrogenase which catalyzes the reversible reduction of the active androgen, DIHYDROTESTOSTERONE to 5 ALPHA-ANDROSTANE-3 ALPHA,17 BETA-DIOL. It also has activity towards other 3-alpha-hydroxysteroids and on 9-, 11- and 15- hydroxyprostaglandins. The enzyme is B-specific in reference to the orientation of reduced NAD or NADPH. 3 alpha-Hydroxysteroid Dehydrogenase,3 alpha-Hydroxysteroid Dehydrogenase (B-Specific),3 alpha-Hydroxysteroid Oxidoreductase,3alpha-Hydroxysteroid Dehydrogenase (B-specific),5 alpha-3 alpha-Hydroxysteroid Dehydrogenase,5 alpha-Dihydroprogesterone 3 alpha-Hydroxysteroid Oxidoreductase,5-DP-3 alpha-HSO,NADPH-5 alpha-Dihydroprogesterone 3 alpha-Hydroxysteroid Oxidoreductase,3 alpha Hydroxysteroid Dehydrogenase,3 alpha Hydroxysteroid Oxidoreductase,5 alpha Dihydroprogesterone 3 alpha Hydroxysteroid Oxidoreductase,Dehydrogenase, 3 alpha-Hydroxysteroid,NADPH 5 alpha Dihydroprogesterone 3 alpha Hydroxysteroid Oxidoreductase,Oxidoreductase, 3 alpha-Hydroxysteroid
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus

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