Focus Eberconazole – Pharmacological and clinical review

Latha Subramanya Moodahadu-Bangera, Jacintha Martis1, Rajan Mittal, Binny Krishnankutty, Naveen Kumar, Shantala Bellary, Sunoj Varughese, Parinitha K. Rao1

INTRODUCTION diagnosis, deviation from classical clinical presentation, emergence of drug resistance, poor compliance and Constant exposure to the ubiquitous fungi has made man increase in immuno-suppressed conditions. With vulnerable to fungal infections. Fungal infections of the effective treatment, the cure rate is high, even though skin are prevalent globally, with 20-25% of the world’s relapses and exacerbations are common. population being affected.[1] Life-time risk of acquiring [2] a dermatophytic infection is estimated to be 10-20%. Currently fungal infections are treated with either oral Climatic conditions, cultural and socioeconomic or topical antifungal agents depending upon the site factors not only contribute to the increased prevalence and severity of infection. Oral antifungal agents are in tropics but also influence the type of fungal infection used only to treat widespread skin lesions, systemic [3] in a particular geographic area. fungal infections and in cases unresponsive to topical therapy. Dermatophytosis is superficial skin infection caused by dermatophytes (specifically Trichophyton, Topical preparations with good local bioavailability Epidermophyton and Microsporum species), which are the most commonly used and preferred first line attach to keratin, colonize the keratinized tissue using keratin as nutrition.[4] Since the infection is limited to agents in the treatment of localized dermatomycosis. the superficial layers of skin, topical application of Their better efficacy which aims to shorten the antifungal agents is helpful in the treatment. Selecting treatment period, fewer side effects, minimization of a suitable antifungal agent is difficult as the market is recurrence, and ease of application enhances patient flooded with many products. Moreover, treatment has compliance resulting in better therapeutic response. become challenging and complex due to difficulties in Eberconazole, a newer antimycotic agent, an derivative, initially designed and investigated in Spain Global Medical Affairs, Dr. Reddy’s Laboratories Ltd., Hyderabad, by the Wassermann investigation centre, later acquired 1Department of Dermatology, Fr Muller Medical College, Mangalore, India by Laboratories Salvat, was launched in 2005 for the treatment of cutaneous fungal infections. In this article Address for correspondence: Dr. Latha Subramanya, G-5, Mount Meru Apt Road, 5, Avenue 7, Banjara Hills, we have reviewed the pharmacology and compared the Hyderabad - 500 034, India. clinical efficacy of eberconazole with other antifungal E-mail: [email protected] agents commonly used in clinical practice.

Access this article online EBERCONAZOLE Quick Response Code: Website: www.ijdvl.com Structure DOI: Eberconazole ((1-(2,4-dichloro-10,11-dihydro-5H- 10.4103/0378-6323.93651 dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole))[5] PMID: [Figure 1], with a molecular formula C -H -C -N , is ***** 18 14 l2 2 a broad-spectrum antifungal agent.

How to cite this article: Moodahadu-Bangera LS, Martis J, Mittal R, Krishnankutty B, Kumar N, Bellary S, et al. Eberconazole - Pharmacological and clinical review. Indian J Dermatol Venereol Leprol 2012;78:217-22. Received: October, 2011. Accepted: December, 2011. Source of Support: Nil. Conflict of Interest: Dr. M S Latha, Dr. Rajan Mittal, Dr. Binny Krishnankutty, Dr. Shantala B, Mr. Sunoj Varughese are the employees of Dr. Reddy’s Laboratories Ltd., which is marketing eberconazole in India. These authors are stakeholders having financial stakes in Dr. Reddy’s Laboratories Ltd. by means of salary, company stocks or both. Dr. Naveen Kumar B R was a former employee of Dr. Reddy’s Laboratories Ltd and is presently not having any stakes in Dr. Reddy’s Laboratories Ltd. Dr. Jacintha Martis and Dr. Parinitha K Rao do not have any conflict of interest.

Indian Journal of Dermatology, Venereology, and Leprology | March-April 2012 | Vol 78 | Issue 2 217 Latha, et al. Eberconazole - A review

amino acids, inorganic phosphate and nucleotides from the fungal cell leading to cell death.

The anti-inflammatory activity comparable to acetyl and ketoprofen,[7] shown in vivo by eberconazole is attributable to the inhibition of 5-lipooxygenase and to a lesser extent of cyclooxygenase-2.[10]

In vitro studies Fernandez-Torres et al. compared the in vitro activity of eberconazole with that of , and against 200 strains of dermatophytes belonging to 19 species of fungi. Among the four drugs tested, eberconazole exhibited the lowest Figure 1: Molecular structure of Eberconazole (Source: ChemBlink available from http://www.chemblink.com/products/128326-82-9.htm minimal inhibitory concentration (MIC) for majority accessed on 10 October 2011) of the dermatophytic strains (P<0.05), suggesting an advantage of eberconazole over other widely used Spectrum of activity agents.[11] Eberconazole has been shown to have broad antimicrobial spectrum of activity in vitro,[6] to be In another in vitro study, eberconazole was shown to effective in dermatophytosis, candidiasis, infection be as efficacious as or even better than clotrimazole by other yeasts such as Malassezzia furfur and and ketoconazole against various strains of Candida causative agents of pityriasis versicolor in in vitro especially C. krusei and C. glabrata, which are usually and animal studies.[6- 8] Its effectiveness against most resistant to triazoles.[7] triazoleresistant yeasts (Candida krusei and Candida glabrata)[9] and also resistant Candida Preclinical studies albicans has been demonstrated in vitro.[7] It has also In preclinical studies using experimental models of been shown to be effective against Gram-positive superficial fungal infections, eberconazole has been bacteria.[8] shown to exhibit similar efficacy to clotrimazole, ketoconazole and better efficacy than .[10] Eberconazole is distinct from other as it has The studies showed that eberconazole is well been to shown to have anti-inflammatory activity,[7] tolerated without any delayed hypersensitivity or which favors its use in the management of inflamed photosensitivity reactions. Also, no phototoxic effects dermatophytic infections. were seen and no significant systemic absorption was observed with eberconazole.[7,12] Mechanism of action Eberconazole exerts fungicidal or fungistatic activity Human pharmacokinetics depending on concentration, being fungicidal at higher After topical application of eberconazole 2% cream in concentration and fungistatic at lower concentrations. healthy volunteers, its concentration in human plasma and urine were below the lower limits of detection Eberconazole prevents fungal growth by inhibiting (<1.1 ng/ml for plasma and <1.0 ng/ml for urine) when ergosterol synthesis, an essential component of the analyzed by high performance liquid chromatography.[10] fungal cytoplasmic membrane leading to structural and functional changes. It prevents the fungal ergosterol However, data on metabolism and excretion of topical synthesis by inhibiting lanosterol 14α-demethylase eberconazole are not available.[7] enzyme that is responsible for the formation of 14 α-methylsterols (precursor of ergosterols). Studies have Efficacy shown that eberconazole binds to the phospholipid Efficacy and safety of topical eberconazole have fraction of the cell and affects sterol synthesis been established by a number of studies. Twice daily intracellularly.[10] At high concentrations, it causes the application of eberconazole 1% was found to be as leakage of small molecules such as potassium ions, efficacious as eberconazole 2% in 60 patients with

218 Indian Journal of Dermatology, Venereology, and Leprology | March-April 2012 | Vol 78 | Issue 2 Latha, et al. Eberconazole - A review mycologically proven tinea corporis and tinea cruris, in a (eberconazole 21.5%, clotrimazole 24.3%). There was phase II pilot study, but the measured parameters did not no statistically significant difference between the show any statistical significance. Overall clinical cure rate of reinfection and relapse in both the groups.[9] rate post therapy was 73.3-93.3% in different groups. Subgroup analysis of the same study showed that in ITT Adverse effects were seen more with eberconazole 2% population, clinical efficacy (defined as the percentage than with 1%, but without any statistical significance.[13] effective response at week 4 of treatment) was higher with eberconazole (66.17%) than with clotrimazole Further, efficacy of eberconazole has been compared (60.63%). In patients with pityriasis versicolor and with the widely used topical antifungals in various candidiasis, no significant difference in therapeutic studies. In a double blind study, eberconazole 1% efficacy was noted with both agents [Table 3].[10,16] cream’s therapeutic efficacy and safety profile was Secondary analysis which included symptomatology, similar to miconazole. After 4 weeks of therapy, 76.09% time to cure, results at week 4 and the investigators patients on eberconazole showed effective response impression, did not show any statistically significant [10] compared to 75.0% in miconazole group [Table 1]. differences.[10] In another study, eberconazole was Therapeutic effects of eberconazole with clotrimazole more effective against dermatophytosis with a [14] and miconazole are compared in Table 2. In another response rate of 61% (for clotrimazole 46%) than multicentric double blind randomized study, Repiso candidiasis (effective response for clotrimazole 73% Montero et al. compared the efficacy of eberconazole and eberconazole 50%). Overall efficacy was 72% for 1% cream with miconazole 2% cream in the treatment eberconazole and 61% for clotrimazole. There was no of dermatophytosis. In this study, eberconazole showed significant difference in relapse in both groups, 4% similar efficacy and safety profile with miconazole in in clotrimazole and 1% relapse in eberconazole was the treatment of dermatophyte infection. This study noted.[17] also suggested that eberconazole can be considered a good alternative for the treatment of dermatophytosis A phase III Indian study (n=92) with a treatment as it has good safety and tolerability profile.[15] duration of 4 weeks followed by another 4 weeks follow-up, confirmed the earlier findings that Another double blind, randomized control study eberconazole 1% is significantly effective against showed that the overall efficacy and safety of cutaneous dermatomycoses. The therapeutic efficacy eberconazole cream in patients with cutaneous was 97.44%; cure rate defined as negative microscopy mycoses including dermatophytosis, candidiasis and pityriasis versicolor, was slightly higher (Per and culture and reduction in total symptom score ≤1 protocol (PP): 74.3% intention to treat (ITT): 61.7%) was 84.62% and improvement defined as negative in comparison to clotrimazole (PP: 67.8% ITT:58.4%) microscopy and culture and reduction in total at week 10, though the differences were statistically symptom score=2 was 12.82%. Only one patient not significant. However, eberconazole showed failed to respond to treatment (failure to respond a significantly greater (P=0.011) efficacy than was defined as negative microscopy and culture and clotrimazole in the treatment of dermatophytosis. Of reduction in total symptom score > 2 or microscopic 94.5% culture-positive patients (eberconazole 95.4%, and/or culture positive, independent of total symptom clotrimazole 93.8%) at baseline, only 25.9% at week score). Clinical improvement was seen within 4 and 23.9% at week 10 remained culture positive 2 weeks of therapy indicating an early response with eberconazole. Its good safety profile was confirmed as only one patient reported mild burning sensation Table 1: Comparison of therapeutic response of Eberconazole over the site of application, which disappeared with and Miconazole in dermatophytosis* continued treatment (Data on file).[18] Parameter Eberconazole (%) Miconazole (%) Therapeutic response 76.09 75.00 Safety rate (cure + improvement) In a phase I study of single and multiple doses of at week 4 topical eberconazole 2% use, no significant and Complete cure at week 4 69.57 69.32 Mycological cure rate at 86.95 84.09 evaluable changes were noted in vital signs, blood week 4 or urine biochemical parameters of the volunteers. Eberconazole 1% cream is as effective as Miconazole 2% cream in the Eberconazole was not detected either in plasma or treatment of dermatophytosis, *Source: Data on file. From Innovators [10] (LaboratoriosSalvat, S.A) product information dated 16 Dec 2001 urine indicating no significant systemic absorption.

Indian Journal of Dermatology, Venereology, and Leprology | March-April 2012 | Vol 78 | Issue 2 219 Latha, et al. Eberconazole - A review

Table 2: Comparative profile of Eberconazole and other topical antifungal agents* Parameter Eberconazole Clotrimazole Miconazole Chemical nature Imidazole Imidazole Imidazole Mechanism of action Sterol synthesis inhibitor; Alters cell Sterol synthesis inhibitor; Alters Sterol synthesis inhibitor; Alters cell membrane permeability cell membrane permeability membrane permeability Spectrum of activity Broad spectrum, fungicidal. Broad spectrum, fungicidal. Broad spectrum, fungistatic. Active against wide range of clinically Active against wide range of Active against wide range of relevant dermatophytes, yeasts and clinically relevant dermatophytes, clinically relevant dermatophytes, Malassezia furfur. yeasts and M. furfur. yeasts and M. furfur. Active against most triazole resistant yeasts such as C. glabrata and C. krusei. Active against even fluconazole resistant C. albicans. Therapeutic indications Cutaneous candidiasis, Tinea versicolor, Dermatophytosis, T. versicolor, Dermatophytosis, T. versicolor, and dermatophytosis and cutaneous candidiasis due and cutaneous candidiasis due to to C. albicans C. albicans Dosing schedule Twice daily Twice daily Twice daily *Source: Adapted from High WA. Fitzpatrick J E. Topical antifungal agents. In: Freedberg IM, Eisen AZ, Wolff K, Austen KF, editors. Fitzpatrick’s Dermatology in General Medicine. Seventh ed: McGraw Hill, 2008 p. 2116-18 and Innovators (LaboratoriosSalvat, S.A) product information. Dated 16 Dec 2001

Table 3: Comparison of therapeutic response of eberconazole the only change observed was slight erythema that and clotrimazole in dermatomycoses in ITT population* appeared for the first time on day 3 (lasting 3days). Clinical condition Eberconazole (%) Clotrimazole (%) Later on day 9, two volunteers reported reddening (zone Dermatophytosis covered with eberconazole 2%) with light granulation Effective response to 66.17 60.63 associated with a mild pruritus and burning sensation therapy at 4 weeks of 1 and 3 days duration, and on day 10 one volunteer Effective response to 61.70 58.4 presented with light erythema that lasted 12 hours.[10] therapy at the end of 10 weeks Candidiasis Further, in a phase II study, eberconazole shared Effective response to 63.64 80.77 similar safety profile with clotrimazole, as there was therapy at 4 weeks no significant difference in the occurrence of AEs. Effective response to 63.64 84.62 Erythema and pruritus were the commonly seen AEs therapy at the end of in this study [Table 4]. Mild irritation was seen in 10 weeks† three of 60 patients and two patients withdrew from Pityriasis versicolor [13] Effective response to 84.09 80.95 the study due to severe skin irritation. In a phase therapy at 4 weeks III study, 20% patients in eberconazole group and Effective response to 81.82 78.57 26% in clotrimazole group withdrew prematurely therapy at the end of due to AEs in patients with candidiasis.[17] In another 10 weeks (Considering missing values as failures), †The percentage effective response was phase III study, local cutaneous irritation was seen in the same in those treated with Eberconazole at week 4 and week 10, *Source: 6.1% of patients in eberconazole group and in 3.7% Innovators (LaboratoriosSalvat, S.A) product information dated 16 Dec 2001 in clotrimazole group without any systemic or serious events and the difference between the two groups was Another phase I study demonstrated that topical not significant.[10] eberconazole 1% (0.1 g), does not induce photosensitivity and phototoxicity indicating its good tolerability.[19] In two studies which evaluated eberconazole for its a) topical and general tolerability, b) eventual On topical application, safety, tolerability and adverse development of sensitization, c) local availability, event (AE) profile of eberconazole was similar to that and d) degree of systemic absorption, the only change of placebo. On single dose application, mild symptoms observed was slight redness in a few volunteers after which were common to eberconazole and placebo both active and placebo applications. This remitted were reported within the first hour. On multiple spontaneously without intervention and the study dose application, mild pruritus, occasional burning was continued with the administration of repeated sensation, and mild skin dryness were seen with increasing doses. A few participants described mild eberconazole and placebo as well, without showing side effects which occurred in areas where placebo a dose effect relationship. In the objective evaluation, or eberconazole were applied, mainly within the

220 Indian Journal of Dermatology, Venereology, and Leprology | March-April 2012 | Vol 78 | Issue 2 Latha, et al. Eberconazole - A review

Table 4: Comparison of adverse reactions of eberconazole activity against yeast and fungi, high efficacy in the and clotrimazole preclinical studies led to its clinical development Adverse reaction* Treatment to explore safety and efficacy in humans. Its anti- Eberconazole (%) Clotrimazole (%) inflammatory action and efficacy against gram positive Erythema 41.2 26.7 bacteria can add to its efficacy in inflamed cutaneous Pustules 5.9 0.0 mycoses and in secondary infections, favoring the Pruritus 17.6 40.0 regression of inflammatory symptoms and treatment Stinging 5.9 20.0 compliance. Folliculitis 5.9 0.0 All 11.8 6.7 Eberconazole is clinically effective in the treatment of Self-induced eczema 5.9 0.0 topical fungal infections, with a good safety profile and (scratching) good tolerability. It has acceptable topical availability Other 5.9 6.7 with no detectable systemic drug levels, and does not Total 100 100 appear to cause skin sensitivity.[20] *Percentage out of total adverse events, Eberconazole and Clotrimazole shared a similar safety profile, Source: Data on file. From Innovators (LaboratoriosSalvat, S.A) product information dated 16 Dec 2001 Eberconazole was more active in vitro against a broad range of dermatophyte species than the other topical first hour of application. The most frequent adverse drugs tested suggesting that it may be a good alternative effect after the first application was coldness, and for the topical treatment of dermatophytosis.[11] after repeated increasing-doses was itching. No Various clinical studies have documented its efficacy signs or symptoms of skin reactivity were observed in the treatment of dermatophytosis. Eberconazole following re-exposure to the product. Vital signs showed greater therapeutic efficacy than clotrimazole (systolic and diastolic blood pressure, heart rate and 1% and equivalent efficacy with miconozole 2% in the body temperature), ECG, or analytical parameters management of dermatophytosis and was similar in (clinical hematology and biochemistry) did not show efficacy in the management of cutaneous candidiasis any clinically significant or relevant changes. The and pityriasis versicolor.[12] quantity of compound collected through washing gauzes decreased progressively over time. Plasma and The results of study in Indian patients[17] has confirmed urine concentrations of eberconazole were below the the earlier findings that eberconazole 1% is significantly quantification limits of the analytical method at all effective against cutaneous dermatomycoses and the times. This study has confirmed that eberconazole reported AEs were similar to that seen in other studies cream is a topical anti-mycotic drug having good local indicating that it is well tolerated in majority of patients. and general tolerability. It also showed acceptable topical availability without detectable systemic drug Data, available on eberconazole, is quite limited. Data [20] levels, and did not appear to cause skin sensitivity. on its metabolism and excretion are still not available[7] No phototoxicity or photosensitivities were seen with thereby requiring further studies. Although it is [7] topical application of eberconazole1% cream. effective against triazole resistant yeasts,[8] it is found to be less effective clinically compared to clotrimazole Formulation advantage 1%[16] thereby limiting its use in this condition. Eberconazole has been marketed as a cream with Moreover, comparative efficacy is yet to be established a characteristic lipophilic-hydrophilic molecular with allylamines and other new antifungal agents. structure for better penetration of fungal cell membrane and prolonged duration of action. The The rise in fungal infections due to increase in galenic components of this topical azole favor and incidence of immunocompromised states, change in optimize the drug’s action in the skin, fatty acid esters socioeconomic and cultural states is demanding an facilitate penetration in the skin and make the cream effective antimycotic agent for the treatment and cure. easy to spread, while polyacrylamides produce a Superficial fungal infections being more prevalent in filmogenous effect and facilitate the continuance of tropical countries, an antimycotic agent having good the active principle in the skin.[12] safety profile and better efficacy with less chance of developing drug resistance such as eberconazole is DISCUSSION always welcome.

Eberconazole’s broad spectrum of anti-mycotic With newer antifungal agents flooding the market,

Indian Journal of Dermatology, Venereology, and Leprology | March-April 2012 | Vol 78 | Issue 2 221 Latha, et al. Eberconazole - A review eberconazole’s effectiveness in the treatment of a wide 7. Thomson Reuters Pharma™ [Internet]. Drug report: range of cutaneous fungal infection in comparison with Eberconazole. Thomson Reuters Pharma™. Updated on 12/ Aug/2010. the existing and newer agents has to be established 8. Font E, Freixes J, Julve J. Profile of a new topical antimycotic, to determine its place in the topical therapy of fungal eberconazole. Revista iberoamericana De Micologia 1995;12:16- infections in future. 7. 9. Rubin AI, Bagheri B, Scher RK. Six novel antimycotics. Am J Clin Dermatol 2002;3:71-81. CONCLUSION 10. Laboratorios Salvat, S.A (Innovators). Product information. 2001. 11. Fernández-Torres B, Inza I, Guarro J. In vitro activities of the Complexities in the treatment of dermatomycosis have new antifungal drug eberconazole and three other topical compelled the invention of newer antifungal agents with agents against 200 strains of dermatophytes. J Clin Microbiol better efficacy and safety profile. Proven better efficacy, 2003;41:5209-11. 12. Martin-Gonzalez B, Vilata-Corell JJ, Linares ML, Laguna- good safety and tolerability profile of eberconazole Argente C, Roche-Gamon E. Treatment in superficial cutaneous along with lack of sensitizing ability make it an mycoses with eberconazole [Spanish]. Med Clin 2006;126:47-50. attractive and suitable alternative in the management 13. del Palacio A, Cuétara S, Rodríguez Noriega A. Topical treatment of tineacorporis and tineacruris with eberconazole (WAS 2160) of dermatomycosis. However, further comparative cream 1% and 2%: a phase II dose-finding pilot study. Mycoses studies with other commonly used agents are required 1995;38:317-24 to position eberconazole among topical antifungals. 14. High WA, Fitzpatrick JE. Topical antifungal agents. In: Freedberg IM, Eisen AZ, Wolff K, Austen KF, editors. Fitzpatrick’s Dermatology in General Medicine. 7th ed. New York: McGraw REFERENCES Hill; 2008. p. 2116-8. 15. Repiso Montero T, López S, Rodríguez C, del Rio R, Badell A, 1. Havlickova B, Czaika VA, Friedrich M. Epidemiological trends Gratacós MR. Eberconazole 1% cream is an effective and in skin mycoses worldwide. Mycoses 2008;51:2-15. safe alternative for dermatophytosis treatment: multicenter, 2. Drake LA, Dinehart SM, Farmer ER, Goltz RW, Graham GF, randomized, double-blind, comparative trial with miconazole Hardinsky MK, et al. Guidelines of care for superficial mycotic 2% cream. Int J Dermatol 2006;45:600-4. infections of the skin: tinea corporis, tinea cruris, tinea faciei, tinea 16. Fonseca Capdevila E. Effectiveness of Eberconazole 1% manuum, and tinea pedis. J Am Acad Dermatol 1996;34:282-6. cream as opposed to Clotrimazole 1% cream in patients with 3. Charles AJ. Superficial cutaneous fungal infections in tropical cutaneous mycosis. Skin 2004;19:480-4. countries. Dermatol Ther 2009;22:550-9. 17. del Palacio A, Ortiz FJ, Pérez A, Pazos C, Garau M, Font E. A 4. Nelson MM, Martin AG, Heffernan MP. Superfecial fungal double blind randomized comparative trial: eberconazole 1% infections: Dermatophytosis, Onychomycosis, Tinea Nigra, cream versus clotrimazole 1% cream twice daily in Candida Piedra. In: Freedberg IM, Eisen AZ, Wolff K, Austen KF, and dermatophyte skin infections. Mycoses 2001;44:173-80. Goldsmith LA, Katz SI, editors.Fitzpatrick’s Dermatology in 18. Dr. Reddy’s Laboratories Ltd. Efficacy and safety evaluation of General Medicine. 6th ed. New York: McGraw Hill; 2003. p. 1989. Eberconazole in cutaneous dermatomycoses. CT report 2006. 5. Eberconazole [internet]. North Carolina: ChemBlink Inc.; Available 19. Rius-Tarruella J, López-Bertran R, Viayna-Cardona C. A phase I from: http://www.chemblink.com/products/128326-82-9.htm. [last photosensitivity/phototoxicity study of eberconazole cream in cited on 2011 Oct 10]. twelve healthy subjects. Publicadona Piel 2005;20:314-6. 6. Zalacain A, Obrador C, Martinez JP, Vinas M, Vinuesa T. 20. Barbanoj MJ, Antonijoan R, Garcia-Gea C, Puntes M, Gich I, Characterization of the antimicrobial susceptibility of Jane F. Eberconazole cream: topical and general tolerability, fungi responsible for onychomycosis in Spain. Med Mycol sensitisation potential, and systemic availability. Met Find Exp 2011;49:495-9. Clin Pharmacol 2005;27:227-34.

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