Rilopirox ‐ a New Hydroxypyridone Antifungal with Fungicidal Properties

Raether, W.; Hänel, H.

doi:10.1111/myc.1990.33.4.191

Cited by 9 publications

(5 citation statements)

References 10 publications

(6 reference statements)

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“…Rilopirox is the second hydroxypyridone to be developed as an antifungal [1]. The first was ciclopirox olamine which is now available as a topical antifungal [3,13].…”

Section: Discussionmentioning

confidence: 99%

“…In contrast to ciclopirox olamine (HOE 296), a previously developed antifungal drug in the chemical class of pyridones, rilopirox exhibits an improved efficacy, especially against yeasts [1,3,4], Fungicidal rates against Tri chophyton mentagrophytes and Candida albi cans under proliferative and non-proliferative conditions are higher than those achieved with common azole and allylamine antifungals [1,2], Furthermore, it has an extremely low resorption rate resulting in a long-term availability of the fungicidal drug in the epi dermis [5]. Rilopirox is hardly soluble in wa ter and has a low toxicity [1,5]. For these rea sons rilopirox appears to be a compound which could be successfully introduced for the treatment of oral, vaginal or cutaneous my coses [6].…”

Section: Introductionmentioning

confidence: 99%

“…Rilopirox (HOE 351) is a novel hydroxypyridone antifungal with outstanding fungicidal properties against a large number of patho genic dermatophytes, yeasts and moulds [1,2], Its chemical name is 6-[4-(4-chlorophenoxy)-phenoxy-methyl]-1-hydroxy-4-methyl-2(lH)pyridone (CAS number: 104153-37-9). In contrast to ciclopirox olamine (HOE 296), a previously developed antifungal drug in the chemical class of pyridones, rilopirox exhibits an improved efficacy, especially against yeasts [1,3,4], Fungicidal rates against Tri chophyton mentagrophytes and Candida albi cans under proliferative and non-proliferative conditions are higher than those achieved with common azole and allylamine antifungals [1,2], Furthermore, it has an extremely low resorption rate resulting in a long-term availability of the fungicidal drug in the epi dermis [5].…”

Section: Introductionmentioning

confidence: 99%

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In vitro Susceptibility Testing of <i>Malassezia furfur</i> against Rilopirox

Nenoff¹,

Haustein²

1997

Skin Pharmacol Physiol

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The in vitro antifungal activity of the new hydroxypyridone antimycotic rilopirox has been evaluated against 29 separate clinical isolates of Mαlαsseziα (M.) furfur obtained from patients with pityriasis versicolor, seborrhoeic dermatitis or dandruff. Minimum inhibitory concentrations (MICs) of rilopirox were measured by the agar dilution technique and, in comparison, by a recently described microdilution method with colorimetric detection of the MIC end points. Rilopirox was found to be able to inhibit growth of all clinical yeast isolates. For the investigated M. furfur strains MIC values from 12.5 to 50 µg ml^-1 with a median of 25 µg ml^-1 were determined by the agar dilution method. Using the microdilution technique, MIC values between 16 and 128 µg ml^-1 (median 32 µg ml^-1) were found for the M. furfur isolates. It has to be taken into account that with a 0.3% solution concentrations of 300,000 µg ml^-1 are applied to the skin. Furthermore, due to its extreme low penetration rilopirox is long-term available in the skin in inhibiting concentrations. In comparison with rilopirox, the in vitro susceptibility of M. furfur against the systemically applicable triazole antimycotic itraconazole and clotrimazole, an established topical antifungal, was tested. As expected, low MIC values for these azoles were found by the agar dilution method. The median of the MIC of M. furfur was 0.1 µg ml^-1 for itraconazole, and 6.25 µg ml^-1 for clotrimazole. The inhibitory effectivity of rilopirox against clinical isolates of M. furfur seems to justify its therapeutic evaluation in clinical trials. This new antifungal may be a useful alternative not only in pityriasis versicolor but also in seborrhoeic dermatitis due to the growth inhibition of M. furfur.

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“…Rilopirox is the second hydroxypyridone to be developed as an antifungal [1]. The first was ciclopirox olamine which is now available as a topical antifungal [3,13].…”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

In vitro Susceptibility Testing of <i>Malassezia furfur</i> against Rilopirox

Nenoff¹,

Haustein²

1997

Skin Pharmacol Physiol

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“…It has been designed as a second drug belonging to the class of hydroxypyridones with good antifungal activity, but it has not yet been used for clinical therapy. It has very low water solubility 4 . At a concentration of 5 μ g ml −1 it had damaging effects on rabbit blastocysts 5…”

Section: Introductionmentioning

confidence: 99%

In vitroinvestigations on the mode of action of the hydroxypyridone antimycotics rilopirox and piroctone onCandida albicans

Sigle

Schäfer‐Korting

Körting³

et al. 2006

Mycoses

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Rilopirox and piroctone belong to the class of hydroxypyridone antimycotics. This class is not related to other antimycotics. In contrast to azole antimycotics and polyene antimycotics the mode of action of hydroxypyridone antimycotics is not fully understood. Inhibition of cellular uptake of essential compounds as well as loss of other compounds seems to be only a secondary effect of a primary not known action of these drugs. The antifungal effect in vitro depends on the medium used. The hyphal induction of Candida albicans is inhibited by hydroxypyridone antimycotics, but this effect is compensated by iron ions. A damage of the cell membrane and a direct influence on adenosine triphosphate synthesis, respectively, do not seem to be part of the mode of action. But there are clear hints that reactive oxygen species (ROS) and available metabolic activity are important parts of the mode of action of the hydroxypyridone antimycotics rilopirox and piroctone.

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“…The biological activity spectrum of this compound is very broad [1][2][3][4][5][6]. MN is used against various anaerobic microorganisms in clinical and surgical practice [1,2] and also in the radiological treatment of oncological diseases as a radiosensitizer of hypoxic cells [3].…”

mentioning

confidence: 99%

Polarographic investigation of the metronidazole complex with polyvinylpyrrolidone*

Vakul’skaya

Ларина

Лопырев

2012

Chem Heterocycl Comp

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Polarographic behavior of the metronidazole complex with polyvinylpyrrolidone in Britton-Robinson buffer solutions have been studied. This complex possesses prolonged antimicrobial action. Complexation with polyvinylpyrrolidone was shown to alter the mechanism of metronidazole reduction and increases its solubility in water. The temperature dependence of the limiting currents indicates the formation of additional hydrogen bonds in the complex, which restricts diffusion of the depolarizer to the cathode.Keywords: 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole, metronidazole, polyvinylpyrrolidone, Britton-Robinson buffer media, complexes, electrochemical reduction, hydrogen bond, polarography.1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole (metronidazole (MN)) was first synthesized in 1957 and at the present time it is the most well studied 5-nitroimidazole drug. The biological activity spectrum of this compound is very broad [1][2][3][4][5][6]. MN is used against various anaerobic microorganisms in clinical and surgical practice [1,2] and also in the radiological treatment of oncological diseases as a radiosensitizer of hypoxic cells [3].The antibacterial, antiprotozoal, and radioprotective properties of metronidazole and other nitroheterocycles [7][8][9][10][11][12] are attributed to their rather low reduction potential and capacity to undergo one-electron transfer [9,[13][14][15][16][17][18][19][20] to give intermediate free radicals, which is confirmed by polarography and EPR [6,21]. However, metronidazole has two significant disadvantages, namely, low solubility in water (about 1 g in 100 ml water) [22] and rapid elimination from the body, which necessitate its repeated introduction during a single day to maintain the required therapeutic dose.The electrochemical reduction of metronidazole itself in buffer media has been studied in many works [23][24][25][26][27]. Investigations were carried out on the effect of pH on the potential and mechanism of its reduction [23]. The correlation between the reduction potential on one hand, and the radioprotective properties [26], antimicrobial activity [8], and capacity of metronidazole to inhibit DNA synthesis [24] on the other hand, were also studied. The recent review by Chadha et al. [28] has been devoted to the increase in bioefficiency and the study of the efficiency of numerous drug-polyvinylpyrrolidone (PVP) systems by various methods. However, a review of the literature has shown that no polarographic study of the effect of PVP on the redox properties of metronidazole had yet been carried out.We have previously discovered that the efficiency of metronidazole against the agents of many anaerobic infections is significantly enhanced when it interacts with PVP [29] and shown that metronidazole in aqueous solution forms a complex with PVP. This complex was shown to possess prolonged action and, in combination with antibiotics, enhances the effect of the latter [29,30], which permits using lower daily drug doses and avoid side effects [31].The aim of the present work was t...

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Rilopirox ‐ a New Hydroxypyridone Antifungal with Fungicidal Properties

Cited by 9 publications

References 10 publications

In vitro Susceptibility Testing of <i>Malassezia furfur</i> against Rilopirox

In vitro Susceptibility Testing of <i>Malassezia furfur</i> against Rilopirox

In vitroinvestigations on the mode of action of the hydroxypyridone antimycotics rilopirox and piroctone onCandida albicans

Polarographic investigation of the metronidazole complex with polyvinylpyrrolidone*

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