Fluorine NMR studies of the metabolism of flumecinol (3-trifluoromethyl-alpha-ethylbenzhydrol). 1993

L A Sylvia, and J T Gerig
Department of Chemistry, University of California-Santa Barbara 93106.

High-resolution and surface coil fluorine-19 NMR spectroscpies have been used to study the metabolism of the liver inducer 3-trifluoromethyl-alpha-ethylbenzhydrol (flumecinol) in rats. Although the fluorine chemical shift range exhibited by metabolites is small, it is possible to identify a number of metabolites or classes of metabolites by direct examination of urine samples. 3-Trifluoromethyl-4'-hydroxy-alpha-ethylbenzhydrol was confirmed as the primary metabolite at low doses (42 mg/kg). At higher doses other metabolites characterized by ring and side chain hydroxylation or further oxidation of the parent compound become apparent. NMR evidence for two previously unrecognized metabolites is described but these structures have not been identified. Studies of liver induction are reported that show that a single large dose of flumecinol exerts a substantial inducing effect on the number and types of metabolites formed after several hours postingestion. Examination of liver metabolism of the drug in vivo showed a single broad resonance, and it was not possible to obtained resolved signals for individual metabolites under the conditions of these experiments. However, nuclear Overhauser experiments showed that the materials detected in the in vivo experiments do not interact significantly with the macromolecular components of the liver.

UI MeSH Term Description Entries
D008099 Liver A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances. Livers
D008297 Male Males
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D001743 Urinary Bladder A musculomembranous sac along the URINARY TRACT. URINE flows from the KIDNEYS into the bladder via the ureters (URETER), and is held there until URINATION. Bladder,Bladder Detrusor Muscle,Detrusor Urinae,Bladder Detrusor Muscles,Bladder, Urinary,Detrusor Muscle, Bladder,Detrusor Muscles, Bladder
D005461 Fluorine A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries. Fluorine-19,Fluorine 19
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001559 Benzhydryl Compounds Compounds which contain the methyl radical substituted with two benzene rings. Permitted are any substituents, but ring fusion to any of the benzene rings is not allowed. Diphenylmethyl Compounds,Compounds, Benzhydryl,Compounds, Diphenylmethyl
D013997 Time Factors Elements of limited time intervals, contributing to particular results or situations. Time Series,Factor, Time,Time Factor
D017207 Rats, Sprague-Dawley A strain of albino rat used widely for experimental purposes because of its calmness and ease of handling. It was developed by the Sprague-Dawley Animal Company. Holtzman Rat,Rats, Holtzman,Sprague-Dawley Rat,Rats, Sprague Dawley,Holtzman Rats,Rat, Holtzman,Rat, Sprague-Dawley,Sprague Dawley Rat,Sprague Dawley Rats,Sprague-Dawley Rats
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus

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