Structural Determination of Rat Urinary Metabolites of Sodium 2-[4-(2-Oxocyclopentylmethyl) phenyl] propionate Dihydrate (Loxoprofen Sodium), a New Anti-inflammatory Agent

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概要

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• The main metabolites of loxoprofen sodium were isolated from rat urine by column chromatography. Their chemical structures were determined on the basis of spectral data and by comparison of the metabolites with authentic samples to be as follows : the parent acid (M-0), two reduction products, i.e., the cis-alcohol (M-1) and the trans-alcohol (M-2), the α-hydroxy ketone (M-3) and three diol metabolites (M-4,M-5 and M-6). The established metabolite structures all indicated that metabolic reactions of loxoprofen in rats occur only at the cyclopentanone moiety. The trans-alcohol metabolite, which has a high inhibitory activity on prostaglandin (PG)-synthetase, was determined to be optically pure, with (2S, 1'R, 2'S)-configurations, by high performance liquid chromatography (HPLC) analysis after derivatization to the diastereomeric amide of the carboxy group with (-)-α-phenylethylamine reagent, and subsequently to the ester of the hydroxy function using (-)-α-methoxy-α-trifluoromethylphenylacetyl chloride.

• 公益社団法人日本薬学会の論文
• 1984-01-25

著者

• 田中 頼久

  三共(株)分析代謝研究所

• 田中 頼久

  Analytical and Metabolic Research Laboratories Sankyo Co.

• 林 了三

  三共(株)分析代謝研究所

• 林 了三

  Analytical and Metabolic Research Laboratories, Sankyo Co., Ltd.

• 成戸 俊二

  Chemical Research Laboratories Sankyo Co., Ltd.

• 寺田 敦佑

  Chemical Research Laboratories Sankyo Co., Ltd.

• 寺田 敦佑

  Chemical Research Laboratories Sankyo Co. Ltd.

• 成戸 俊二

  三共

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