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Mechanism for interference of ethinamate in Zimmermann test for determination of urinary 17-ketosteroids.

The mechanism by which dosage of ethinamate elevates falsely the values for the urinary 17-ketosteroids has been investigated. A specimen of urine collected following oral administration of ethinamate to man was hydrolyzed with sulfuric acid and then extracted with dichloromethane. From the urinary extract two non-steroidal chromogens responsible for the Zimmermann reaction were isolated. The spectral and chromatographic properties indicated that these chromogens would be 1-acetylcyclohex-1-en-4-ol and 1-acetylcyclohex-1-en-5-ol. Their structures were unequivocally characterized by comparison with the synthetic samples. It has been disclosed that during the acid-catalyzed hydrolysis of the conjugates in the process of 17-ketosteroids determination the 4- and 3-hydroxylated metabolites formed from ethinamate are converted artificially into the ketones which give a typical color for the 17-ketosteroids in the Zimmermann reaction.