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The pharmacological activities of five metabolites of an anti-inflammatory compound, 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) were investigated and compared with TAI-284 and phenylbutazone. The metabolite IIb (cis3'-hydroxy-cyclohexyl, β-form) was almost equivalent to TAI-284 regarding antiinflammatory activity as estimated by the carrageenin edema test, and was more active than TAI-284 in the analgesic activity estimated by the phenylquinone writhing test and determination of the ulcerogenic activity. The metabolites IIa (cis-4'hydroxy-cyclohexyl) and IV (cis-3'-hydroxy-cyclohexyl, α-form) had about half the anti-inflammatory activity and one third to one quarter the analgesic activity of TAI-284, however the degree of ulcerogenicity was considerably lower than that of TAI-284. 1 (4'-oxo-cyclohexyl) was less active, and III (trans-4'-hydroxy-cyclohexyl) showed the weakest activity comparable to that of phenylbutazone. Antipyretic activities of all five metabolites were much lower than those of TAI-284. As the pharmacological activities of metabolites varied greatly according to the position of the hydroxyl group on the cyclohexane ring of TAI-284, it is feasible that the distribution pattern and affinity of the metabolites for receptors could be modified.

Biological Activities of Metabolites of 6-Chloro-5-Cyclohexylindan-l-Carboxylic Acid (TA1-284: Anti-Inflammatory Agent)