메뉴 건너뛰기




Volumn 35, Issue 15, 1992, Pages 2818-2825

Stereoisomers of Ketoconazole: Preparation and Biological Activity

Author keywords

[No Author keywords available]

Indexed keywords

AROMATASE; CHOLESTEROL 7ALPHA MONOOXYGENASE; CYTOCHROME P450; DRUG METABOLIZING ENZYME; KETOCONAZOLE; LYASE; OXYGENASE;

EID: 0026703849     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00093a015     Document Type: Article
Times cited : (116)

References (42)
  • 1
    • 0018720357 scopus 로고
    • Antimycotic Imidazoles. 4. Synthesis and antifungal activity of Ketoconazole, a new potent orally active broad spectrum antifungal agent
    • Heeres, J.; Backx, L. J. J.; Mostmans, J. H.; Van Cutsem, J. Antimycotic Imidazoles. 4. Synthesis and antifungal activity of Ketoconazole, a new potent orally active broad spectrum antifungal agent. J. Med. Chem. 1979, 22, 1003-1005.
    • (1979) J. Med. Chem. , vol.22 , pp. 1003-1005
    • Heeres, J.1    Backx, L.J.J.2    Mostmans, J.H.3    Van Cutsem, J.4
  • 2
    • 0020057397 scopus 로고
    • Ketoconazole: A review of its therapeutic efficacy in superficial and systemic fungal infections
    • Heel, R. C.; Brogden, R. N.; Carmine, A.; Morley, P. A.; Speight, T. M.; Avery, G. S. Ketoconazole: A review of its therapeutic efficacy in superficial and systemic fungal infections. Drugs 1982, 23,1-36.
    • (1982) Drugs , vol.23 , pp. 1-36
    • Heel, R.C.1    Brogden, R.N.2    Carmine, A.3    Morley, P.A.4    Speight, T.M.5    Avery, G.S.6
  • 4
    • 84987039943 scopus 로고
    • Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: the inhibition of isoprenoid biosynthesis
    • Vanden Bossche, H.; Lauwers, W.; Willemsens, G.; Marichal, P.; Comelisson, F.; Cools, W. Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: the inhibition of isoprenoid biosynthesis. Pestic. Sci. 1984, 13, 188-198.
    • (1984) Pestic. Sci. , vol.13 , pp. 188-198
    • Vanden, B.H.1    Lauwers, W.2    Willemsens, G.3    Marichal, P.4    Comelisson, F.5    Cools, W.6
  • 5
    • 0022167826 scopus 로고
    • Biochemical targets for antifungal azole derivatives: Hypothesis on the mode of action
    • Vanden Bossche, H. Biochemical targets for antifungal azole derivatives: Hypothesis on the mode of action. Curr. Top. Med. Mycol. 1985, 1, 313-351.
    • (1985) Curr. Top. Med. Mycol. , vol.1 , pp. 313-351
    • Bossche1
  • 6
    • 0023550589 scopus 로고
    • Effects of ketoconazole on cholesterol synthesis and precursor concentrations in the rat liver
    • Strandberg, T. E.; Tilvis, R. S.; Miettinen, T. A. Effects of ketoconazole on cholesterol synthesis and precursor concentrations in the rat liver. Lipids 1984, 22, 1020-1024.
    • (1984) Lipids , vol.22 , pp. 1020-1024
    • Strandberg, T.E.1    Tilvis, R.S.2    Miettinen, T.A.3
  • 7
    • 0022548601 scopus 로고
    • Effects of ketoconazole on cholesterol synthesis
    • Kraemer, F. B.; Spilman, S. D. Effects of ketoconazole on cholesterol synthesis. Pharmacol. Exp. Ther. 1986, 238, 905-911.
    • (1986) Pharmacol. Exp. Ther. , vol.238 , pp. 905-911
    • Kraemer, F.B.1    Spilman, S.D.2
  • 8
    • 0022540312 scopus 로고
    • Inhibition of cholesterol synthesis by ketoconazole
    • Kraemer, F. B.; Pont, A. Inhibition of cholesterol synthesis by ketoconazole. Am. J. Med. 1986, 80, 616-622.
    • (1986) Am. J. Med. , vol.80 , pp. 616-622
    • Kraemer, F.B.1    Pont, A.2
  • 9
    • 0023865658 scopus 로고
    • Cholesterol metabolism during ketoconazole treatment in man
    • Miettinen, T. A. Cholesterol metabolism during ketoconazole treatment in man. J. Lipid Res. 1988, 29, 43-51.
    • (1988) J. Lipid Res. , vol.29 , pp. 43-51
    • Miettinen, T.A.1
  • 10
    • 0026025024 scopus 로고
    • Hypolipidemic effect and mechanism of ketoconazole without and with cholestyramine in familial hypercholesterolemia
    • Gylling, H.; Vanhanen, H.; Miettinen, T. A. Hypolipidemic effect and mechanism of ketoconazole without and with cholestyramine in familial hypercholesterolemia. Metabolism 1991, 40, 35-41.
    • (1991) Metabolism , vol.40 , pp. 35-41
    • Gylling, H.1    Vanhanen, H.2    Miettinen, T.A.3
  • 11
    • 0011832475 scopus 로고
    • The rational design of fungal lanosterol C14 demethylase inhibitors
    • Marriott, M. S. The rational design of fungal lanosterol C14 demethylase inhibitors. Molecular aspects of chemotherapy. Proc. Int. Sym. Mol. Aspects Chemo., 2nd, Meeting Date 1988, Borowski, E., Shugar, D., Eds.; Pergamon: Oxford, U.K., 1990: Chapter 16, pp 193-202.
    • (1990) Molecular aspects of chemotherapy. Proc. Int. Sym. Mol. Aspects Chemo. , pp. 193-202
    • Marriott, M.S.1
  • 13
    • 0021171723 scopus 로고
    • Ketoconazole: a potent inhibitor of cytochrome P-450 dependent drug metabolism in rat liver
    • Sheets, J. J.; Mason, J. I. Ketoconazole: a potent inhibitor of cytochrome P-450 dependent drug metabolism in rat liver. Drug Metab. Dispos. 1984, 12, 603-606.
    • (1984) Drug Metab. Dispos. , vol.12 , pp. 603-606
    • Sheets, J.J.1    Mason, J.I.2
  • 14
    • 0023601787 scopus 로고
    • Inhibition of testicular 17a-hydroxylase and 17,20-lyase but not 3/5-hydroxysteroid dehydrogenaseisomerase or 17/5-hydroxysteroid oxidoreductase by ketoconazole and other imidazole drugs
    • Ayub, M.; Levell, M. J. Inhibition of testicular 17a-hydroxylase and 17,20-lyase but not 3/5-hydroxysteroid dehydrogenaseisomerase or 17/5-hydroxysteroid oxidoreductase by ketoconazole and other imidazole drugs. J. Steroid Biochem. 1987, 28, 521-531.
    • (1987) J. Steroid Biochem. , vol.28 , pp. 521-531
    • Ayub, M.1    Levell, M.J.2
  • 15
    • 0023874047 scopus 로고
    • Inhibitory effects of ketoconazole and miconazole on cytochrome P-450 mediated oxidative metabolism of testosterone and xenobiotics in mouse hepatic microsomes—comparative study with cimetidine
    • Morita, K.; Takeshi, O.; Shimakawa, H. Inhibitory effects of ketoconazole and miconazole on cytochrome P-450 mediated oxidative metabolism of testosterone and xenobiotics in mouse hepatic microsomes—comparative study with cimetidine. J. Pharmacobio-Dyn. 1988,11, 106-114.
    • (1988) J. Pharmacobio-Dyn. , vol.11 , pp. 106-114
    • Morita, K.1    Takeshi, O.2    Shimakawa, H.3
  • 16
    • 0024211692 scopus 로고
    • A comparative study of 1-substituted imidazole and 1,2,4-triazole antifungal compounds as inhibitors of testosterone hydroxylations catalysed by mouse hepatic microsomal cytochromes P-450
    • Ballard, S. A.; Lodola, A.; Tarbit, M. H. A comparative study of 1-substituted imidazole and 1,2,4-triazole antifungal compounds as inhibitors of testosterone hydroxylations catalysed by mouse hepatic microsomal cytochromes P-450. Biochem. Pharmacol. 1988, 37, 4643-4651.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 4643-4651
    • Ballard, S.A.1    Lodola, A.2    Tarbit, M.H.3
  • 17
    • 0022620562 scopus 로고
    • Effects of high dose ketoconazole therapy on the main plasma testicular and adrenal steroids in previously untreated prostatic cancer patients
    • De Coster, R.; Caere, I.; Coene, M. C.; Amery, W.; Beerens, D.; Haelterman, C. Effects of high dose ketoconazole therapy on the main plasma testicular and adrenal steroids in previously untreated prostatic cancer patients. Clin. Endocrinol. 1980, 24, 657-664.
    • (1980) Clin. Endocrinol. , vol.24 , pp. 657-664
    • De Coster, R.1    Caere, I.2    Coene, M.C.3    Amery, W.4    Beerens, D.5    Haelterman, C.6
  • 18
    • 0020576066 scopus 로고
    • Site of action of low dose ketoconazole on androgen biosynthesis in man
    • Santen, R. J.; De Coster, R. Site of action of low dose ketoconazole on androgen biosynthesis in man. J. Clin. Endodrinol. Metab. 1983, 57, 732-736.
    • (1983) Clin. Endodrinol. Metab. , vol.57 , pp. 732-736
    • Santen, R.J.1    De Coster, R.2
  • 20
    • 0021331551 scopus 로고
    • Effect of ketoconazole and other imidazole fungicides on testosterone biosynthesis
    • Schürmeyer, Th.; Nieschlag, E. Effect of ketoconazole and other imidazole fungicides on testosterone biosynthesis. Acta Endocrinol. 1984,105, 275-280.
    • (1984) Acta Endocrinol. , vol.105 , pp. 275-280
    • Schürmeyer, T.1    Nieschlag, E.2
  • 22
    • 0020739427 scopus 로고
    • The effects of ketoconazole on steroidogenesis in cultured mouse adrenal cortex tumor cells
    • Kowal, J. The effects of ketoconazole on steroidogenesis in cultured mouse adrenal cortex tumor cells. Endocrinology 1983, 112, 1541-1543.
    • (1983) Endocrinology , vol.112 , pp. 1541-1543
    • Kowal, J.1
  • 23
    • 0020531983 scopus 로고
    • Ketoconazole blocks adrenal steroidogenesis by inhibiting cytochrome P-450 dependent enzymes
    • Loose, D. S.; Kan, P. B.; Hirst, M. A.; Marcus, R. A.; Feldman, D. Ketoconazole blocks adrenal steroidogenesis by inhibiting cytochrome P-450 dependent enzymes. J. Clin. Invest. 1983, 71, 1495-1499.
    • (1983) J. Clin. Invest. , vol.71 , pp. 1495-1499
    • Loose, D.S.1    Kan, P.B.2    Hirst, M.A.3    Marcus, R.A.4    Feldman, D.5
  • 25
    • 84986980108 scopus 로고
    • Diastereoisomers and enantiomers of paclobutrazol: Their preparation and biological activity
    • Sugavanam, B. Diastereoisomers and enantiomers of paclobutrazol: Their preparation and biological activity. Pestic. Sci. 1984, 15, 296-302.
    • (1984) Pestic. Sci. , vol.15 , pp. 296-302
    • Sugavanam, B.1
  • 26
    • 0022452345 scopus 로고
    • Stereoselective interaction of enantiomers of diniconazole, a fungicide, with purified P-450i4dm from yeast
    • Yoshida, Y.; Aoyama, Y.; Takano, H.; Kato, T. Stereoselective interaction of enantiomers of diniconazole, a fungicide, with purified P-450i4dm from yeast. Biochem. Biophys. Res. Commun. 1986, 137, 513-519.
    • (1986) Biochem. Biophys. Res. Commun. , vol.137 , pp. 513-519
    • Yoshida, Y.1    Aoyama, Y.2    Takano, H.3    Kato, T.4
  • 27
    • 0024157536 scopus 로고
    • Synthesis and structure-activity relationships of a novel antifungal agent ICI 195,739
    • Boyle, F. T.; Gilman, D. J.; Gravestock, M. B.; Wardleworth, J. M. Synthesis and structure-activity relationships of a novel antifungal agent ICI 195,739. Ann. N.Y. Acad. Sci. 1988,544, 86-100.
    • (1988) Ann. N.Y. Acad. Sci. , vol.544 , pp. 86-100
    • Boyle, F.T.1    Gilman, D.J.2    Gravestock, M.B.3    Wardleworth, J.M.4
  • 29
    • 0025334852 scopus 로고
    • Stereoselective interaction of an azole antifungal agent with its target, Lanosterol 14a-demethylase (cytochrome P-45014DM): A model study with stereoisomers of triadimenol and purified cytochrome P-450i4Dm from yeast
    • Yoehida, Y.; Aoyoma, Y. Stereoselective interaction of an azole antifungal agent with its target, Lanosterol 14a-demethylase (cytochrome P-45014DM): A model study with stereoisomers of triadimenol and purified cytochrome P-450i4Dm from yeast. Chirality 1990, 2, 10-15.
    • (1990) Chirality , vol.2 , pp. 10-15
    • Yoehida, Y.1    Aoyoma, Y.2
  • 30
  • 31
    • 85021505899 scopus 로고
    • Quantitative structure activity relationships of fungicidally active triazoles: analogs and stereoisomers of propiconazole and etaconazole
    • Ebert, E.; Eckhardt, W.; Jaekel, K.; Moser, P.; Sozzi, D.; Vogel, C. Quantitative structure activity relationships of fungicidally active triazoles: analogs and stereoisomers of propiconazole and etaconazole. Z. Naturforsch C: Biosci. 1989, 44, 86-96.
    • (1989) Z. Naturforsch C: Biosci. , vol.44 , pp. 86-96
    • Ebert, E.1    Eckhardt, W.2    Jaekel, K.3    Moser, P.4    Sozzi, D.5    Vogel, C.6
  • 32
    • 85021499214 scopus 로고
    • Preparation, testing, formulation of a propiconazole enantiomer devoid of phytotoxic activity
    • EP 300413, January 25
    • Aebi, R.; Hubele, A.; Speich, J. Preparation, testing, formulation of a propiconazole enantiomer devoid of phytotoxic activity. Eur. Pat. Appl. EP 300413, January 25, 1989.
    • (1989) Eur. Pat. Appl.
    • Aebi, R.1    Hubele, A.2    Speich, J.3
  • 33
    • 84986974452 scopus 로고
    • Structure-activity relationships in a group of azoles, with special reference to 1,3-dioxolan-2-ylmethyl derivatives
    • Heeres, J. Structure-activity relationships in a group of azoles, with special reference to 1,3-dioxolan-2-ylmethyl derivatives. Pestic. Sci. 1984, 15, 268-279.
    • (1984) Pestic. Sci. , vol.15 , pp. 268-279
    • Heeres, J.1
  • 35
    • 0019949059 scopus 로고
    • Cytochrome P-450 induction by Clofibrate. Purification and properties of a cytochrome P-450 relatively specific for the 12- and 11-hydroxylation of dodecanoic acid (lauric acid)
    • Gibson, G. G.; Orton, T. C.; Tumburia, R. P. Cytochrome P-450 induction by Clofibrate. Purification and properties of a cytochrome P-450 relatively specific for the 12- and 11-hydroxylation of dodecanoic acid (lauric acid). Biochem. J. 1982, 203, 161-168.
    • (1982) Biochem. J. , vol.203 , pp. 161-168
    • Gibson, G.G.1    Orton, T.C.2    Tumburia, R.P.3
  • 36
    • 0023643411 scopus 로고
    • Regioselective progesterone hydroxylation catalyzed by eleven rat hepatic cytochrome P-450 isozymes
    • Swinney, D. C.; Ryan, D. E.; Thomas, P. E.; Levin, W. Regioselective progesterone hydroxylation catalyzed by eleven rat hepatic cytochrome P-450 isozymes. Biochemistry 1987, 26, 7073-7083.
    • (1987) Biochemistry , vol.26 , pp. 7073-7083
    • Swinney, D.C.1    Ryan, D.E.2    Thomas, P.E.3    Levin, W.4
  • 37
    • 0025607166 scopus 로고
    • Effect of the cytochrome P-450 inhibitor, ketoconazole, and the NADPH 5a-reductase inhibitor, 4-MA, upon the metabolic profile in human, monkey, dog and rat
    • Swinney, D. C. Progesterone metabolism in hepatic microsomes. Effect of the cytochrome P-450 inhibitor, ketoconazole, and the NADPH 5a-reductase inhibitor, 4-MA, upon the metabolic profile in human, monkey, dog and rat. Drug Metab. Dispos. 1990, 18, 859-865.
    • (1990) Drug Metab. Dispos. , vol.18 , pp. 859-865
    • Swinney, D.C.1
  • 38
    • 0022540843 scopus 로고
    • Age- and sex-related expression of cytochromes P450f and P450g in rat liver
    • Bandiera, S.; Ryan, D. E.; Levin, W.; Thomas, P. E. Age- and sex-related expression of cytochromes P450f and P450g in rat liver. Arch. Biochem. Biophys. 1986, 248, 658-676.
    • (1986) Arch. Biochem. Biophys. , vol.248 , pp. 658-676
    • Bandiera, S.1    Ryan, D.E.2    Levin, W.3    Thomas, P.E.4
  • 39
    • 0001507078 scopus 로고
    • Isolation from adrenal cortex of a nonmembrane iron protein and a flavoprotein functional as a reduced triphosphopyridine nucleotide-cytochrome P450 reductase
    • Omura, T.; Sander, E.; Estabrook, R. W.; Cooper, D. Y.; Rosenthal, O. Isolation from adrenal cortex of a nonmembrane iron protein and a flavoprotein functional as a reduced triphosphopyridine nucleotide-cytochrome P450 reductase. Arch. Biochem. Biophys. 1966, 117, 660-673.
    • (1966) Arch. Biochem. Biophys. , vol.117 , pp. 660-673
    • Omura, T.1    Sander, E.2    Estabrook, R.W.3    Cooper, D.Y.4    Rosenthal, O.5
  • 40
    • 0022460824 scopus 로고
    • Rat hepatic cholesterol 7a-hydroxylase: Biochemical properties and comparison to constitutive and xenobiotic-inducible cytochrome P-450 enzymes
    • Waxman, D. J. Rat hepatic cholesterol 7a-hydroxylase: Biochemical properties and comparison to constitutive and xenobiotic-inducible cytochrome P-450 enzymes. Arch. Biochem. Biophys. 1986, 247, 335-345.
    • (1986) Arch. Biochem. Biophys. , vol.247 , pp. 335-345
    • Waxman, D.J.1
  • 42
    • 0023875216 scopus 로고
    • Determination of microsomal lauric acid hydroxylase activity by HPLC with flow-through radiochemical quantitation
    • Romano, M. C.; Straub, K. M.; Yodis, L. A. P.; Eckardt, R. D.; Newton, J. F. Determination of microsomal lauric acid hydroxylase activity by HPLC with flow-through radiochemical quantitation. Anal. Biochem. 1988,170, 83-93.
    • (1988) Anal. Biochem. , vol.170 , pp. 83-93
    • Romano, M.C.1    Straub, K.M.2    Yodis, L.A.P.3    Eckardt, R.D.4    Newton, J.F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.