Detail of "67915-31-5"

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Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: the inhibition of isoprenoid biosynthesis

Correction of: Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: the inhibition of isoprenoid biosynthesis. Vanden Bossche, Hugo; Lauwers, Wim; Willemsens, Gustaaf; Marichal, Patrick; Cornelissen, Frans; Cools, Willy (Dep. Comp. Biochem., Janssen Pharm. Res. Lab., Beerse B-2340, Belg.). Pestic. Sci., 15(2), 188-98 (English) 1984. CODEN: PSSCBG. ISSN: 0031-613X. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemical Bioregulators) The antimycotic N-substituted imidazoles and triazoles, such as imazalil [35554-44-0], ketoconazole [65277-42-1], and itraconazole [84625-61-6], interfere selectively at low concns. (30.01 nM) with the 14a-demethylase system (which is dependent on cytechrome P 450 [9035-51-2] of fungal cells, for example, Candida albicans and Penicillium italicum. This results in a decreased availability of ergosterol [57-87-4] and the accumulation of 14a-methyl-sterols such as lanosterol [79-63-0]. Cholesterol [57-88-5] synthesis in a subcellular fraction of rat liver, in intact fibroblasts, and in vivo in rat liver, was much less sensitive, for example, to ketoconazole. The imidazole derivs. imazalil, miconazole [22916-47-8], ketoconazole, and parconazole [61400-59-7], and the triazole derivs. propiconazole [60207-90-1], terconazole [67915-31-5], and triaconazole affect the cytochrome P 450 species of microsomal fractions from Saccharomyces cerevisiae and rat liver. Cytochrome P 450 of rat-liver microsomes was much less sensitive to these azole derivs., in parallel with the lower sensitivity of cholesterol synthesis. Using unilamellar vesicles composed of phosphatidylcholine, phosphatidylethanolamine, and diphosphatidylcholine, multilamellar vesicles of dipalmitoylphosphatidylcholine, and intact S. cerevisiae, the substitution of ergosterol by lanosterol leads to functional changes in the membranes. The selective interaction of the azole derivs. with the yeast microsomal cytochrome P 450 leads to the accumulation of 14a-methyl-sterols and results in changes in the permeability of the membranes and leakages. The obsd. inhibition of growth may have its origin in these changes. Miconazole, ketoconazole and deacylated ketoconazole (R-39519) [67914-61-8] also affect the growth of Staphylococcus aureus, miconazole being 12.5 and 14 times, resp., more active than R-39519 and ketoconazole. The greater antibacterial activity of miconazole coincides with its greater inhibition of the biosynthesis of C-55 isoprenoid alc. and vitamin K. The phosphorylated deriv. of C-55 isoprenoid alc. has functional importance in the biosynthesis of bacterial cell wall and membrane polymers, and the menaquinone vitamin K plays a role in the electron transport of Gram-pos. bacteria. The reduced synthesis of these vital compds. may contribute to the antibacterial activity of miconazole.

Enantiomeric separation of ketoconazole and terconazole antifungals by electrokinetic chromatography: Rapid quantitative analysis of ketoconazole in pharmaceutical formulations

Enantiomeric separation of ketoconazole and terconazole antifungals by electrokinetic chromatography: Rapid quantitative analysis of ketoconazole in pharmaceutical formulations. Castro-Puyana, Maria; Crego, Antonio L.; Marina, M. Luisa ( Departamento de Quimica Analitica, Facultad de Quimica, Universidad de Alcala, Madrid, Spain). Electrophoresis, 26(20), 3960-3968 (English) 2005 Wiley-VCH Verlag GmbH & Co. KGaA.Some chemicals with cas registry numbers like 67915-31-5 are also used. CODEN: ELCTDN. ISSN: 0173-0835. DOCUMENT TYPE: Journal CA Section: 64 (Pharmaceutical Analysis) EKC using a neutral CD as chiral selector was applied in this work to the development of a method enabling the enantiomeric sepn. of ketoconazole and terconazole antifungals. The influence of different exptl. conditions such as temp., CD concn., pH, and nature and concn. of the buffer on the enantiomeric resoln. of the compds. studied was investigated. The use of 10 mM heptakis-(2,3,6-tri-O-methyl)-b-CD in a 100 mM phosphate buffer (pH 3.5) with a temp. of 15°C allowed the sepn. of the enantiomers of ketoconazole and terconazole with high resoln. (Rs > 2.0). The rapid sepn. of ketoconazole enantiomers with an anal. time < 3 min was carried out after fitting some exptl. parameters. The developed method was applied to the detn. of ketoconazole in different pharmaceutical formulations. .