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  • 1
    Electronic Resource
    Electronic Resource
    Microbial and Mammalian Metabolism Studies on the Semisynthetic Antimalarial, Deoxoartemisinin (1995)
    Springer
    Pharmaceutical research 12 (1995), S. 1493-1498 
    Details
    ISSN: 1573-904X
    Keywords: antimalarial ; deoxoartemisinin ; microbial ; metabolites ; mammalian ; metabolism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. Deoxoartemisinin is a semisynthetic antimalarial with potential for treatment of multiple drug resistant malaria. Metabolism studies were conducted to aid in future drug development. Methods. Microbial model systems were employed which have been shown to be good predictors of mammalian drug metabolites. Metabolism studies using rats were also performed. Results. Three microbial metabolites of deoxoartemisinin were identified (2, 3, and 4). Metabolite 3 was also found in rat plasma. HPLC/MS analyses were performed on the rat plasma using 2, 3, and 4 as standards. All metabolites were thoroughly characterized by 1H and 13C-NMR. An additional rat plasma metabolite was revealed and it was shown not to be 9α-hydroxyartemisinin. Conclusions. Deoxoartemisinin was metabolized to three microbial metabolites. Metabolism by rats showed the presence of two metabolites in the plasma, one of which was the same as the microbial metabolite.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1016239505506
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Microbial and Mammalian Metabolism Studies of the Semisynthetic Antimalarial, Anhydrodihydroartemisinin (1994)
    Springer
    Pharmaceutical research 11 (1994), S. 990-994 
    Details
    ISSN: 1573-904X
    Keywords: microbial and mammalian metabolism ; antimalarial ; anhydrodihydroartemisinin ; microbial and mammalian metabolites ; two-dimensional nuclear magnetic resonance (2D-NMR) techniques ; thermospray liquid chromatography/mass spectroscopy(LC/MS)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Microbial metabolism studies of the semisynthetic antimalarial anhydrodihydroartemisinin (1), have shown that it is metabolized by a number of microorganisms. Large scale fermentation with Streptomyces lavendulaeL-105 and Rhizopogonspecies (ATCC 36060) have resulted in the isolation of four microbial metabolites. These metabolites have been identified as a 14-carbon rearranged product (2), 9β-hydroxyanhydrodihydroartemisinin (3), 1 l-epi-deoxydihydro-artemisinin (4), and 3α-hydroxydeoxyanhydrodihydroartemisinin (5). Microbial metabolites were completely characterized by spectral methods, including 1H-NMR and 13C-NMR spectroscopy. The structure and stereochemistry of metabolite 2 were unequivocally established by X-ray crystallographic analysis. Thermospray mass spectroscopy/high-performance liquid chromatographic analyses of plasma from rats used in mammalian metabolism studies of 1 have shown microbial metabolite 3 to be the major mammalian metabolite. In vitroantimalarial testing has shown metabolite 3 to possess antimalarial activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1018979202933
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Microbial Metabolism Studies of the Antimalarial Drug Arteether (1990)
    Springer
    Pharmaceutical research 7 (1990), S. 199-203 
    Details
    ISSN: 1573-904X
    Keywords: microbial metabolism ; antimalarial ; arteether ; microbial metabolites ; two-dimensional nuclear magnetic resonance (2D-NMR) techniques
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Microbial metabolism studies of the antimalarial drug arteether (1) have shown that arteether is metabolized by a number of microorganisms. Large-scale fermentation with Aspergillus niger (ATCC 10549) and Nocardia corallina (ATCC 19070) have resulted in the isolation of four microbial metabolites which have been characterized using two-dimensional nuclear magnetic resonance (2D-NMR) techniques. These metabolites have been identified as “AEM1” (2), 3α-hydroxydeoxyarteether (3), 3α-hydroxydeoxydihydroartemisinin (4), and deoxydihydroartemisinin (5).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1015845306124
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    Structure Elucidation and Thermospray High-Performance Liquid Chromatography/Mass Spectroscopy (HPLC/MS) of the Microbial and Mammalian Metabolites of the Antimalarial Arteether (1990)
    Springer
    Pharmaceutical research 7 (1990), S. 923-927 
    Details
    ISSN: 1573-904X
    Keywords: microbial and mammalian metabolism ; antimalarial ; arteether ; two-dimensional nuclear magnetic resonance (2D-NMR) techniques ; thermospray liquid chromatography/mass spectros-copy (LC/MS)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Microbial metabolism studies of the antimalarial drug arteether (1) have shown that arteether is metabolized to six new metabolites in addition to those previously reported (3). Large-scale fermentations with Cunninghamella elegans (ATCC 9245) and Streptomyces lavendulae (L-105) have resulted in the characterization of these metabolites primarily by two-dimensional nuclear magnetic resonance (2D-NMR) methods as 9β-hydroxyarteether (2), a ring rearrangement metabolite (3), 3α-hydroxy-11-epi-deoxydihydroartemisinin (4), 9α-hydroxyarteether (5), 2α-hydroxyarteether (6), and 14-hydroxyarteether (7). Thermospray mass spectroscopy/high-performance liquid chromatographic analyses have shown that four of these metabolites (2, 5, 6, 7) are also present in rat liver microsome preparations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1015993722846
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    Paper (German National Licenses)
    Fulltext
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