TY - JOUR T1 - ISOLATION AND STEREOCHEMICAL IDENTIFICATION OF A METABOLITE OF NALTREXONE FROM HUMAN URINE JF - Drug Metabolism and Disposition JO - Drug Metab Dispos SP - 401 LP - 405 VL - 2 IS - 5 AU - NITHIANANDA CHATTERJIE AU - JAMES M. FUJIMOTO AU - CHARLES E. INTURRISI AU - SANDRA ROERIG AU - RICHARD I. H. WANG AU - DAVID V. BOWEN AU - FRANK H. FIELD AU - DONALD D. CLARKE Y1 - 1974/09/01 UR - http://dmd.aspetjournals.org/content/2/5/401.abstract N2 - Pooled urine samples from patients receiving 100-200 mg of naltrexone per day orally were extracted; the basic (alkaloid) compounds derived were isolated by preparative thin-layer chromatography. The major metabolite of naltrexone was found to be an epimer of N-cyclopropylmethyl-14-hydroxy-7,8-dihydronormorphine wherein the 6-keto group of naltrexone had been reduced to yield the 6β-hydroxy epimer (an isomorphine). This conclusion was based on infrared, mass, and nuclear magnetic resonance spectra studies. Furthermore, the reduction product formed in vitro in a soluble chicken liver enzyme system from naltrexone and an in vivo metabolite of naloxone derived from the chicken were found to have the more commonly expected 6α-hydroxy orientation. Copyright © 1974 by The American Society for Pharmacology and Experimental Therapeutics ER -