Benzimidazole drugs and modulation of biotransformation enzymes

Velík, J.; Baliharová, Vendula; Fink‐Gremmels, Johanna; Bull, Sarah; Lamka, J.; Skálová, Lenka

doi:10.1016/j.rvsc.2003.08.005

Cited by 195 publications

(89 citation statements)

References 94 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Même si comparativement à l'efficacité antiplasmodiale sur isolats chloroquinosensible, le dérivé fluoré 6e est 2 fois plus performant, il n'en demeure que vis-à-vis des P. falciparum chloroquino-résistants le composé chloré 6f est de loin 7 fois plus efficace. Comme en série des benzimidazolés anthelminthiques, le blocage du site potentiel de métabolisation C5 du noyau benzimidazole (Velík et al, 2004) serait également indispensable à l'induction de bonnes performances antiplasmodiales en série des benzimidazolyl-chalcones. De plus, au regard du profil chimique des quinoléines antipaludiques, l'on pourrait suggérer que le groupement 5-chlorobenzimidazole se comporterait comme un pharmacophore antiplasmodiale à l'instar de la 7-chloroquinoléine présente dans la structure de l'Amodiaquine et de la Chloroquine.…”

Section: Modulation Des Activités Antiplasmodiales De La Benzimidazolunclassified

Synthèse et criblage antiplasmodial de quelques benzimidazolyl-chalcones

Ouattara¹,

Sissouma²,

Yavo³

et al. 2015

Int. J. Bio. Chem. Sci

View full text Add to dashboard Cite

Section: Modulation Des Activités Antiplasmodiales De La Benzimidazolunclassified

Synthèse et criblage antiplasmodial de quelques benzimidazolyl-chalcones

Ouattara¹,

Sissouma²,

Yavo³

et al. 2015

Int. J. Bio. Chem. Sci

View full text Add to dashboard Cite

“…Benzimidazole drugs inhibit in an irreversible way the glucose uptake leading to the depletion of glycogen storage of the parasites. 13,14) Due to their chemical features, all the benzimidazole drugs are sensitive to light, with a behaviour common to all members of this class of compounds. 13,15) The amine derivative from hydrolysis of the carbamic group has been reported to be the main photodegradation product, indicated also by metabolism studies as the major metabolite of the drugs.…”

Section: -4)mentioning

confidence: 99%

Photo- and Thermal-Stability Studies on Benzimidazole Anthelmintics by HPLC and GC-MS

Ragno

Risoli

Ioele

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Infections by worms represent a serious health problem in the tropical and subtropical regions, when the environmental conditions are especially critical for the drug storage, due to both high temperature and strong sunlight. Under these stressing climatic conditions, the characterization of the thermal-and photo-stability of drugs and drug formulations is of high interest. Light and high temperature can influence a drug formulation, leading to changes in the physico-chemical and therapeutic properties of the active principles. 1-4)The most common drugs used as anthelmintics belong to the benzimidazole series of which the most commercialized in the world are: Albendazole (ALB), Fenbendazole (FEN) and Mebendazole (MEB) [5][6][7][8][9][10][11][12] (Fig. 1). Benzimidazole drugs inhibit in an irreversible way the glucose uptake leading to the depletion of glycogen storage of the parasites. 13,14) Due to their chemical features, all the benzimidazole drugs are sensitive to light, with a behaviour common to all members of this class of compounds. 13,15) The amine derivative from hydrolysis of the carbamic group has been reported to be the main photodegradation product, indicated also by metabolism studies as the major metabolite of the drugs.13) Accordingly, a close monitoring of these drugs, as such or in pharmaceutical formulations, constitutes a noteworthy analytical problem in regions presenting tropical climate. HPLC procedures have been used for determination of MEB, 15) ALB 16,17) and FEN 17) in veterinary formulations whereas only a TLC method for the degradation study of MEB is reported. 11)In the present paper, the studied drugs were exposed to various conditions of stressing light and temperature. The degradation study was performed under controlled conditions, using a cabinet provided with a Xenon lamp, able to simulate the solar light spectrum, and a temperature controller.The photoproducts were monitored by HPLC and characterized by GC-MS. HPLC method was validated by analysis of synthetic mixtures containing different amounts of drugs and photoproducts. HPLC method was finally applied to the analytical control of the drugs commercial formulations. Results and DiscussionPhoto-Degradation Study Ethanol solutions of ALB, FEN and MEB (20 mg/ml) were exposed to controlled irradiation and analyzed at time intervals up to 10 h. Figure 2 shows semi-logarithmic plots of the % residue drug vs. irradiation time. The concentration of the products were obtained as a function of the respective peak areas carried out by HPLC chromatography. The drugs concentration values were carried out by using the relationships reported in Table 1. The exposure to light of the drugs in ethanol solution caused a marked degradation for all the compounds. Figure 3 shows the chromatograms of the ethanol solutions Photo-and thermal-stability of the anthelmintics Albendazole, Mebendazole and Fenbendazole as in solid as in solution form has been investigated, by using a Xenon arc lamp as a radiation source, according to the ICH guideline...

show abstract

“…Stock solutions were stable over prolonged periods of time. Absorbencies of aqueous buffered solutions are proportional to their concentrations up to 1.52 × 10 -5 mol dm -3 (11) and 2.5 × 10 -5 mol dm -3 (13) indicating that there is no significant intermolecular stacking which should give rise to hypochromic effects. Studied compounds 11 and 25 exhibited strong fluorescence emission with maximum at 521 nm and 562 nm.…”

Section: Uv/vis Fluorimetric and CD Titrationsmentioning

confidence: 99%