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Volumn 25, Issue 3, 1997, Pages 301-310

Microbial models of mammalian metabolism: Fungal metabolism of phenolic and nonphenolic p-cymene-related drugs and prodrugs. I. Metabolites of thymoxamine

Author keywords

[No Author keywords available]

Indexed keywords

[4 (2 DIMETHYLAMINOETHOXY) 5 ISOPROPYL 2 METHYLPHENYL] 1 BETA D GLUCOPYRANOSIDE 7; ALPHA ADRENERGIC RECEPTOR BLOCKING AGENT; DESACETYLTHYMOXAMINE O SULFATE 6; MOXISYLYTE DERIVATIVE; NORDESACETYLTHYMOXAMINE 3; PHENOL DERIVATIVE; THYMOXAMINE 1; UNCLASSIFIED DRUG;

EID: 0030942460     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (19)

References (57)
  • 1
    • 0013787808 scopus 로고
    • Competitive blockade of adrenergic receptors and histamine receptors by thymoxamine
    • A. T. Birmingham and J. Szolcsanyi: Competitive blockade of adrenergic receptors and histamine receptors by thymoxamine. J. Pharm. Pharmacol. 17, 449-458 (1965).
    • (1965) J. Pharm. Pharmacol. , vol.17 , pp. 449-458
    • Birmingham, A.T.1    Szolcsanyi, J.2
  • 2
    • 0015298814 scopus 로고
    • Is thymoxamine a specific alpha-adrenoceptor blocking agent?
    • L. Fawke: Is thymoxamine a specific alpha-adrenoceptor blocking agent? Br. J. Pharmacol. 44, 362P-363P (1972).
    • (1972) Br. J. Pharmacol. , vol.44
    • Fawke, L.1
  • 3
    • 0017143271 scopus 로고
    • Effects of alpha-adrenoceptor agonists and antagonists on pre- and postsynaptically located alpha-adrenoceptors
    • G. M. Drew: Effects of alpha-adrenoceptor agonists and antagonists on pre- and postsynaptically located alpha-adrenoceptors. Eur. J. Pharmacol. 36, 313-320 (1976).
    • (1976) Eur. J. Pharmacol. , vol.36 , pp. 313-320
    • Drew, G.M.1
  • 4
    • 0018886238 scopus 로고
    • In vitro and in vivo α-blocking activity of thymoxamine and its two metabolites
    • M. H. Creuzet, G. Prat, A. Malek, F. Fauran, and J. Roquebert: In vitro and in vivo α-blocking activity of thymoxamine and its two metabolites. J. Pharm. Pharmacol. 32,209-213 (1980).
    • (1980) J. Pharm. Pharmacol. , vol.32 , pp. 209-213
    • Creuzet, M.H.1    Prat, G.2    Malek, A.3    Fauran, F.4    Roquebert, J.5
  • 5
    • 0013857881 scopus 로고
    • The nature of the adrenergic receptors of the trachea of the guinea pig
    • R. W. Foster: The nature of the adrenergic receptors of the trachea of the guinea pig. J. Pharm. Pharmacol. 18, 1-12 (1966).
    • (1966) J. Pharm. Pharmacol. , vol.18 , pp. 1-12
    • Foster, R.W.1
  • 6
    • 0023760005 scopus 로고
    • Effects of five alpha-blockers on the hypogastric nerve stimulation of the canine lower urinary tract
    • M. Poirier, J. P. Riffaud, J. Y. Lacolle, and C. Dupont: Effects of five alpha-blockers on the hypogastric nerve stimulation of the canine lower urinary tract. J. Urol. 140, 165-167 (1988).
    • (1988) J. Urol. , vol.140 , pp. 165-167
    • Poirier, M.1    Riffaud, J.P.2    Lacolle, J.Y.3    Dupont, C.4
  • 7
    • 0343222386 scopus 로고
    • Recherche biochimique et pharmacologique de nouveaux alpha-bloquants urosélectifs
    • Jan.
    • J. P. Riffaud: Recherche biochimique et pharmacologique de nouveaux alpha-bloquants urosélectifs. J.A.M.A. (Suppl. French Ed.) 9-12 (Jan. 1992).
    • (1992) J.A.M.A. (Suppl. French Ed.) , pp. 9-12
    • Riffaud, J.P.1
  • 8
    • 0026035252 scopus 로고
    • Effect of moxisylyte on the lower urinary tract. 1. Effect on the isolated rabbit urethra and bladder
    • K. Watanabe, Y. Hayashi, K. Ikeda, and H. Ohnishi: Effect of moxisylyte on the lower urinary tract. 1. Effect on the isolated rabbit urethra and bladder. Folia Pharmacol. Jpn. 97, 145-151 (1991).
    • (1991) Folia Pharmacol. Jpn. , vol.97 , pp. 145-151
    • Watanabe, K.1    Hayashi, Y.2    Ikeda, K.3    Ohnishi, H.4
  • 9
    • 0026026277 scopus 로고
    • Effect of moxisylyte on the lower urinary tract. 2. Effect on the urethra in anesthetized dogs
    • K. Watanabe, Y. Hayashi, K. Ikeda, and H. Ohnishi: Effect of moxisylyte on the lower urinary tract. 2. Effect on the urethra in anesthetized dogs. Folia Pharmacol. Jpn. 97, 153-165 (1991).
    • (1991) Folia Pharmacol. Jpn. , vol.97 , pp. 153-165
    • Watanabe, K.1    Hayashi, Y.2    Ikeda, K.3    Ohnishi, H.4
  • 10
    • 0018622098 scopus 로고
    • Effet d'un medicament alpha-lytique (thymoxamine) sur le profil des pressions de l'urètre
    • A. Zaroli, S. Bernasconi, and P. Bossi: Effet d'un medicament alpha-lytique (thymoxamine) sur le profil des pressions de l'urètre. Arch. Ital. Neurol. Nefrol. 51, 281-289 (1979).
    • (1979) Arch. Ital. Neurol. Nefrol. , vol.51 , pp. 281-289
    • Zaroli, A.1    Bernasconi, S.2    Bossi, P.3
  • 15
    • 0021919692 scopus 로고
    • Metabolism of thymoxamine. III. Structure elucidation of the metabolites and interspecies comparison
    • K.-O. Vollmer and A. VonHodenberg: Metabolism of thymoxamine. III. Structure elucidation of the metabolites and interspecies comparison. Eur. J. Drug Metab. Pharmacokinet. 10, 139-145 (1985).
    • (1985) Eur. J. Drug Metab. Pharmacokinet. , vol.10 , pp. 139-145
    • Vollmer, K.-O.1    Vonhodenberg, A.2
  • 17
    • 0025985933 scopus 로고
    • Pharmacokinetics of a prodrug thymoxamine: Dose-dependence of the metabolite ratio in healthy subjects
    • C. Marquer, J. H. Trouvin, J. Y. Lacolle, C. Dupont, and C. Jacquot: Pharmacokinetics of a prodrug thymoxamine: dose-dependence of the metabolite ratio in healthy subjects. Eur. J. Drug Metab. Pharmacokinet. 16, 183-188 (1991).
    • (1991) Eur. J. Drug Metab. Pharmacokinet. , vol.16 , pp. 183-188
    • Marquer, C.1    Trouvin, J.H.2    Lacolle, J.Y.3    Dupont, C.4    Jacquot, C.5
  • 18
    • 0016250297 scopus 로고
    • Microbial models of mammalian metabolism. Aromatic hydroxylation
    • R. V. Smith and J. P. Rosazza: Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch. Biochem. Biophys. 161, 551-558 (1974).
    • (1974) Arch. Biochem. Biophys. , vol.161 , pp. 551-558
    • Smith, R.V.1    Rosazza, J.P.2
  • 19
    • 0016839144 scopus 로고
    • Microbial models of mammalian metabolism
    • R. V. Smith and J. P. Rosazza: Microbial models of mammalian metabolism. J. Pharm. Sci. 11, 1737-1759 (1975).
    • (1975) J. Pharm. Sci. , vol.11 , pp. 1737-1759
    • Smith, R.V.1    Rosazza, J.P.2
  • 21
    • 0019969958 scopus 로고
    • Glucuronide and sulfate conjugation in the fungal metabolism of aromatic hydrocarbons
    • C. E. Cerniglia, J. P. Freeman, and R. K. Mitchum: Glucuronide and sulfate conjugation in the fungal metabolism of aromatic hydrocarbons. Appl. Environ. Microbiol. 43, 1070-1075 (1982).
    • (1982) Appl. Environ. Microbiol. , vol.43 , pp. 1070-1075
    • Cerniglia, C.E.1    Freeman, J.P.2    Mitchum, R.K.3
  • 22
    • 0027463822 scopus 로고
    • Microbial hydroxylation and glucuronidation of the angiotensin-II (AII) receptor antagonist MK-954
    • T. S. Chen, L. So, R. White, and R. L. Monaghan: Microbial hydroxylation and glucuronidation of the angiotensin-II (AII) receptor antagonist MK-954. J. Antibiot. 46, 131-134 (1993).
    • (1993) J. Antibiot. , vol.46 , pp. 131-134
    • Chen, T.S.1    So, L.2    White, R.3    Monaghan, R.L.4
  • 23
    • 84982406526 scopus 로고
    • Oestratriene 3-beta glucosides preparation by adding 3-hydroxy steroid to a carbohydrate-containing fungal culture medium. German Patent 2,326,084 (19 May 1973)
    • K. Petzoldt, K. Kieslich, and H. Steinbeck (Schering AG): Oestratriene 3-beta glucosides preparation by adding 3-hydroxy steroid to a carbohydrate-containing fungal culture medium. German Patent 2,326,084 (19 May 1973), C.A. 82, 86566s (1975).
    • (1975) C.A. , vol.82
    • Petzoldt, K.1    Kieslich, K.2    Steinbeck, H.3
  • 24
    • 84982064247 scopus 로고
    • Microbiologische Umwandlungen nichsteroider Strukturen. VII. Mikrobielle Glucosidierung einer phenolischen Hydroxylgruppe
    • K. Kieslich, H.-J. Vidic, K. Petzoldt, and G. A. Hoyer: Microbiologische Umwandlungen nichsteroider Strukturen. VII. Mikrobielle Glucosidierung einer phenolischen Hydroxylgruppe. Chem. Ber. 109, 2259-2265 (1976).
    • (1976) Chem. Ber. , vol.109 , pp. 2259-2265
    • Kieslich, K.1    Vidic, H.-J.2    Petzoldt, K.3    Hoyer, G.A.4
  • 26
    • 0020417853 scopus 로고
    • Microbial transformations of natural antitumor agents. 20. Glucosylation of viridicatum toxin
    • M. S. Raju, G. S. Wu, A. Gard, and J. P. Rosazza: Microbial transformations of natural antitumor agents. 20. Glucosylation of viridicatum toxin. J. Natl. Prod. 45, 321-327 (1982).
    • (1982) J. Natl. Prod. , vol.45 , pp. 321-327
    • Raju, M.S.1    Wu, G.S.2    Gard, A.3    Rosazza, J.P.4
  • 27
    • 0022468228 scopus 로고
    • Conversion of zearalenone to zearalenone glycoside by Rhizopus sp.
    • H. Kamimura: Conversion of zearalenone to zearalenone glycoside by Rhizopus sp. Appl. Environ. Microbiol. 52, 515-519 (1986).
    • (1986) Appl. Environ. Microbiol. , vol.52 , pp. 515-519
    • Kamimura, H.1
  • 28
    • 0022655517 scopus 로고
    • Microbial transformations. Part 4(1). Regioselective para hydroxylation of aromatic rings by the fungus Beauveria sulfurescens. the metabolism of isopropyl N-phenyl carbamate (Propham®)
    • B. Vigne, A. Archelas, J.-D. Fourneron, and R. Furstoss: Microbial transformations. Part 4(1). Regioselective para hydroxylation of aromatic rings by the fungus Beauveria sulfurescens. The metabolism of isopropyl N-phenyl carbamate (Propham®). Tetrahedron 42, 2451-2456 (1986).
    • (1986) Tetrahedron , vol.42 , pp. 2451-2456
    • Vigne, B.1    Archelas, A.2    Fourneron, J.-D.3    Furstoss, R.4
  • 29
    • 0023250882 scopus 로고
    • Microbial transformation of zearalenone. I. Formation of zearalenone-4-O-β-glucoside
    • S. ElSharkawy and Y. J. AbulHajj: Microbial transformation of zearalenone. I. Formation of zearalenone-4-O-β-glucoside. J. Natl. Prod. 50. 520-521 (1987).
    • (1987) J. Natl. Prod. , vol.50 , pp. 520-521
    • ElSharkawy, S.1    AbulHajj, Y.J.2
  • 30
    • 0027483259 scopus 로고
    • Microbial models of mammalian metabolism. Furosemide glucoside formation using the fungus Cunninghamella elegans
    • M. Hezari and P. J. Davis: Microbial models of mammalian metabolism. Furosemide glucoside formation using the fungus Cunninghamella elegans. Drug Metab. Dispos. 21, 259-267 (1993).
    • (1993) Drug Metab. Dispos. , vol.21 , pp. 259-267
    • Hezari, M.1    Davis, P.J.2
  • 31
    • 0023915816 scopus 로고
    • Microbial transformation of zearalenone. 2. Reduction, hydroxylation and methylation products
    • S. H. ElSharkawy and Y. J. AbulHajj: Microbial transformation of zearalenone. 2. Reduction, hydroxylation and methylation products. J. Org. Chem. 53, 515-519 (1988).
    • (1988) J. Org. Chem. , vol.53 , pp. 515-519
    • ElSharkawy, S.H.1    AbulHajj, Y.J.2
  • 32
    • 0024947123 scopus 로고
    • Microbial transformation of zearalenone. III. Formation of 2,4-O-β-diglucoside
    • S. H. ElSharkawy: Microbial transformation of zearalenone. III. Formation of 2,4-O-β-diglucoside. Acta Pharm. Jugosl. 39, 303-310 (1989).
    • (1989) Acta Pharm. Jugosl. , vol.39 , pp. 303-310
    • ElSharkawy, S.H.1
  • 34
    • 0024404586 scopus 로고
    • Microbial transformation of flavonoids: Sulfation of 5-hydroxyflavone by Streptomyces fulvissimus
    • A. Ibrahim and Y. J. AbulHajj: Microbial transformation of flavonoids: sulfation of 5-hydroxyflavone by Streptomyces fulvissimus. Appl. Environ. Microbiol. 55, 3140-3142 (1989).
    • (1989) Appl. Environ. Microbiol. , vol.55 , pp. 3140-3142
    • Ibrahim, A.1    AbulHajj, Y.J.2
  • 36
    • 0038761703 scopus 로고
    • A simple, inexpensive procedure for the large scale production of alkyl quinones
    • D. Liotta, J. Arbiser, J. W. Short, and M. Saindane: A simple, inexpensive procedure for the large scale production of alkyl quinones. J. Org. Chem. 48, 2932-2933 (1983).
    • (1983) J. Org. Chem. , vol.48 , pp. 2932-2933
    • Liotta, D.1    Arbiser, J.2    Short, J.W.3    Saindane, M.4
  • 37
    • 33947487193 scopus 로고
    • Conformational studies. VI. Intramolecular hydrogen bonding in non-chair conformations of cis,cis,cis-2,5-dialkyl-1,4-cyclohexanediols
    • R. D. Stolow, P. M. McDonagh, and M. M. Bonaventura: Conformational studies. VI. Intramolecular hydrogen bonding in non-chair conformations of cis,cis,cis-2,5-dialkyl-1,4-cyclohexanediols. J. Am. Chem. Soc. 86, 2165-2170 (1964).
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 2165-2170
    • Stolow, R.D.1    McDonagh, P.M.2    Bonaventura, M.M.3
  • 39
    • 0038538585 scopus 로고
    • Extractive components from incensecedar heartwood (Libocedrus decurrens Torrey). II. Occurrence and synthesis of p-methoxythymol and p-methoxycarvacrol, two new phenolic compounds
    • E. Zavarin and A. B. Anderson: Extractive components from incensecedar heartwood (Libocedrus decurrens Torrey). II. Occurrence and synthesis of p-methoxythymol and p-methoxycarvacrol, two new phenolic compounds. J. Org. Chem. 20, 443-447 (1955).
    • (1955) J. Org. Chem. , vol.20 , pp. 443-447
    • Zavarin, E.1    Anderson, A.B.2
  • 40
    • 0003045608 scopus 로고
    • Triterpenoids and glycosides from Geum japonicum
    • S. Shigenaga, I. Kouno, and N. Kawano: Triterpenoids and glycosides from Geum japonicum. Phytochemistry 24, 115-118 (1985).
    • (1985) Phytochemistry , vol.24 , pp. 115-118
    • Shigenaga, S.1    Kouno, I.2    Kawano, N.3
  • 41
    • 0020383754 scopus 로고
    • Polyuronide biosynthesis by cell free extracts of Mucor rouxii
    • A. Flores-Carreon and S. Bartnicki-Garcia: Polyuronide biosynthesis by cell free extracts of Mucor rouxii. J. Gen. Microbiol. 128, 2023-2027 (1982).
    • (1982) J. Gen. Microbiol. , vol.128 , pp. 2023-2027
    • Flores-Carreon, A.1    Bartnicki-Garcia, S.2
  • 42
    • 0001253934 scopus 로고
    • The synthesis of aryl glycosiduronic acids
    • C. A. Marsh and G. A. Levvy: The synthesis of aryl glycosiduronic acids. Biochem. J. 68, 617-621 (1958).
    • (1958) Biochem. J. , vol.68 , pp. 617-621
    • Marsh, C.A.1    Levvy, G.A.2
  • 43
    • 0027512468 scopus 로고
    • Selective oxidation of monosaccharide derivatives to uronic acids
    • N. J. Davis and S. L. Flitsch: Selective oxidation of monosaccharide derivatives to uronic acids. Tetrahedron Lett. 34, 1181-1184 (1993).
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1181-1184
    • Davis, N.J.1    Flitsch, S.L.2
  • 45
    • 0026326405 scopus 로고
    • Découverte tardive de l'hépatotoxicité des médicaments
    • D. Larrey: Découverte tardive de l'hépatotoxicité des médicaments. Gastroenterol. Clin. Biol. 15, 875 (1991).
    • (1991) Gastroenterol. Clin. Biol. , vol.15 , pp. 875
    • Larrey, D.1
  • 47
    • 0026325240 scopus 로고
    • Moxisylyte: Atteinte hépatique. Un cas avec réadministration positive
    • G. Mignot, G. Dumas, R. M. Chichmanian, and A. Spreux: Moxisylyte: atteinte hépatique. Un cas avec réadministration positive. Gastroenterol. Clin. Biol. 15, 979-980 (1991).
    • (1991) Gastroenterol. Clin. Biol. , vol.15 , pp. 979-980
    • Mignot, G.1    Dumas, G.2    Chichmanian, R.M.3    Spreux, A.4
  • 49
    • 0025746568 scopus 로고
    • Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes
    • K. Öllinger and A. Brunmark: Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. J. Biol. Chem. 266, 21496-21503 (1991).
    • (1991) J. Biol. Chem. , vol.266 , pp. 21496-21503
    • Öllinger, K.1    Brunmark, A.2
  • 50
    • 0342352880 scopus 로고
    • Molecular mechanisms of quinone cytotoxicity
    • P. J. O'Brien: Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 67, 129-138 (1991).
    • (1991) Chem.-Biol. Interact. , vol.67 , pp. 129-138
    • O'Brien, P.J.1
  • 51
    • 0022342880 scopus 로고
    • Modulation of cytotoxicity of menadione sodium bisulfite versus leukemia L1210 by the acid-soluble thiol pool
    • S. A. Akman, M. Dietrich, R. Chlebowski, P. Limberg, and J. B. Block: Modulation of cytotoxicity of menadione sodium bisulfite versus leukemia L1210 by the acid-soluble thiol pool. Cancer Res. 45, 5257-5262 (1985).
    • (1985) Cancer Res. , vol.45 , pp. 5257-5262
    • Akman, S.A.1    Dietrich, M.2    Chlebowski, R.3    Limberg, P.4    Block, J.B.5
  • 52
    • 0024349246 scopus 로고
    • Interconversion of NAD(H) to NADP(H). A cellular response to quinone-induced oxidative stress in isolated hepatocytes
    • C. R. Stubberfield and G. M. Cohen: Interconversion of NAD(H) to NADP(H). A cellular response to quinone-induced oxidative stress in isolated hepatocytes. Biochem. Pharmacol. 38, 2631-2637 (1989).
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 2631-2637
    • Stubberfield, C.R.1    Cohen, G.M.2
  • 54
    • 0028645493 scopus 로고
    • Enzyme-directed bioreductive drug development revisited: A commentary on recent progress and future prospects with emphasis on quinone anticancer agents and quinone metabolizing enzymes, particularly DT-diaphorase
    • P. Workman: Enzyme-directed bioreductive drug development revisited: a commentary on recent progress and future prospects with emphasis on quinone anticancer agents and quinone metabolizing enzymes, particularly DT-diaphorase. Oncol. Res. 6, 461-475 (1994).
    • (1994) Oncol. Res. , vol.6 , pp. 461-475
    • Workman, P.1
  • 55
    • 0029121481 scopus 로고
    • Nicotinamide adenine dinucleotide (phosphate): Quinone oxidoreductase (DT-diaphorase) as a target for bioreductive antitumor quinones: quinone cytotoxicity and selectivity in human lung and breast cancer cell lines
    • H. D. Beall, A. M. Murphy, D. Siegel, R. H. J. Hargreaves, J. Butler, and D. Ross: Nicotinamide adenine dinucleotide (phosphate): quinone oxidoreductase (DT-diaphorase) as a target for bioreductive antitumor quinones: quinone cytotoxicity and selectivity in human lung and breast cancer cell lines. Mol. Pharmacol. 48, 499-504 (1995).
    • (1995) Mol. Pharmacol. , vol.48 , pp. 499-504
    • Beall, H.D.1    Murphy, A.M.2    Siegel, D.3    Hargreaves, R.H.J.4    Butler, J.5    Ross, D.6
  • 56
    • 0028906812 scopus 로고
    • Detoxification ability and toxicity of quinones in mouse and human cell lines used for anticancer drug screening
    • Z. Djuric, T. H. Corbett, F. A. Valeriote, L. K. Heilbrun, and L. H. Baker: Detoxification ability and toxicity of quinones in mouse and human cell lines used for anticancer drug screening. Cancer Chemother. Pharmacol. 36, 20-26 (1995).
    • (1995) Cancer Chemother. Pharmacol. , vol.36 , pp. 20-26
    • Djuric, Z.1    Corbett, T.H.2    Valeriote, F.A.3    Heilbrun, L.K.4    Baker, L.H.5
  • 57
    • 0040379236 scopus 로고
    • Biological oxidation of nitrogen in organic molecules
    • (A. Wiseman, ed.), Ellis Horwood & VCH, Chichester
    • J. W. Gorrod and L. A. Damani (ed.): Biological oxidation of nitrogen in organic molecules. In "Ellis Horwood Health Science Series" (A. Wiseman, ed.), pp. 445. Ellis Horwood & VCH, Chichester, 1985.
    • (1985) Ellis Horwood Health Science Series , pp. 445
    • Gorrod, J.W.1    Damani, L.A.2


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