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The metabolites of (+/-)-5(-)[p(-)[2-(5-ethyl-2- pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione (1, pioglitazone), which is a representative insulin-sensitizing agent, were synthesized to confirm their structures and for studies of their pharmacological properties. Of the metabolites identified, a compound hydroxylated at the 2-position of the ethoxy chain (3) and compounds oxygenated at the ethyl side chain attached to the pyridine ring (4, 5) were found to be active, although the potency was slightly lower than that of the parent compound.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Studies on Antidiabetic Agents. XII. Synthesis and Activity of the Metabolites of (.+-.)-5-(p-(2-(5-Ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione (Pioglitazone).