Biosynthesis, isolation, and identification of 6β‐hydroxynaltrexone, a major human metabolite of naltrexone

Edward J. Cone; Charles W. Gorodetzky; S. Y. Yeh

doi:10.1002/jps.2600640409

Biosynthesis, isolation, and identification of 6β‐hydroxynaltrexone, a major human metabolite of naltrexone

Edward J. Cone, Charles W. Gorodetzky, S. Y. Yeh

School of Medicine

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Chemical reduction of naltrexone is described in an attempt to synthesize 6β‐hydroxynaltrexone. Only the epimer, 6α‐hydroxynaltrexone, was produced. Pilot metabolic studies on naltrexone in the dog, rat, and guinea pig were made to determine which animal produced the greatest amount of 6β‐hydroxynaltrexone. The guinea pig was selected and used to produce the metabolite. Isolation and purification methods are described, and spectral data are presented for structural confirmation of the metabolite.

Original language	English (US)
Pages (from-to)	618-621
Number of pages	4
Journal	Journal of Pharmaceutical Sciences
Volume	64
Issue number	4
DOIs	https://doi.org/10.1002/jps.2600640409
State	Published - Apr 1975

Keywords

6α‐Hydroxynaltrexone—synthesis via chemical reduction of naltrexone
6β‐Hydroxynaltrexone—isolation and identification as naltrexone metabolite in guinea pig
Naltrexone—chemical reduction to 6α‐hydroxynaltrexone, metabolism in dog, rat, and guinea pig

ASJC Scopus subject areas

Pharmaceutical Science

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10.1002/jps.2600640409

Cite this

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title = "Biosynthesis, isolation, and identification of 6β‐hydroxynaltrexone, a major human metabolite of naltrexone",

abstract = "Chemical reduction of naltrexone is described in an attempt to synthesize 6β‐hydroxynaltrexone. Only the epimer, 6α‐hydroxynaltrexone, was produced. Pilot metabolic studies on naltrexone in the dog, rat, and guinea pig were made to determine which animal produced the greatest amount of 6β‐hydroxynaltrexone. The guinea pig was selected and used to produce the metabolite. Isolation and purification methods are described, and spectral data are presented for structural confirmation of the metabolite.",

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year = "1975",

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T1 - Biosynthesis, isolation, and identification of 6β‐hydroxynaltrexone, a major human metabolite of naltrexone

AU - Cone, Edward J.

AU - Gorodetzky, Charles W.

AU - Yeh, S. Y.

PY - 1975/4

Y1 - 1975/4

N2 - Chemical reduction of naltrexone is described in an attempt to synthesize 6β‐hydroxynaltrexone. Only the epimer, 6α‐hydroxynaltrexone, was produced. Pilot metabolic studies on naltrexone in the dog, rat, and guinea pig were made to determine which animal produced the greatest amount of 6β‐hydroxynaltrexone. The guinea pig was selected and used to produce the metabolite. Isolation and purification methods are described, and spectral data are presented for structural confirmation of the metabolite.

AB - Chemical reduction of naltrexone is described in an attempt to synthesize 6β‐hydroxynaltrexone. Only the epimer, 6α‐hydroxynaltrexone, was produced. Pilot metabolic studies on naltrexone in the dog, rat, and guinea pig were made to determine which animal produced the greatest amount of 6β‐hydroxynaltrexone. The guinea pig was selected and used to produce the metabolite. Isolation and purification methods are described, and spectral data are presented for structural confirmation of the metabolite.

KW - 6α‐Hydroxynaltrexone—synthesis via chemical reduction of naltrexone

KW - 6β‐Hydroxynaltrexone—isolation and identification as naltrexone metabolite in guinea pig

KW - Naltrexone—chemical reduction to 6α‐hydroxynaltrexone, metabolism in dog, rat, and guinea pig

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Biosynthesis, isolation, and identification of 6β‐hydroxynaltrexone, a major human metabolite of naltrexone

Abstract

Keywords

ASJC Scopus subject areas

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