2007, Number 4
<< Back Next >>
Dermatología Cosmética, Médica y Quirúrgica 2007; 5 (4)
Butenafine. A review
López GI, Bonifaz A
Language: Spanish
References: 47
Page: 211-217
PDF size: 226.69 Kb.
ABSTRACT
Butenafine is a benzylamine derivative and similar to allylamines, it inhibits biosynthesis of ergosterol,
blocking the squalene epoxidation. It remains at the stratum corneum for 72 hours and has anti-inflammatory
as well as antifungal activity against dermatophytes and other filamentous fungi. It is fungistatic
against
Candida Albicans and
Malassezia Furfur with a low minimum inhibitory concentration (MIC), compared
to other topical antimycotics. Butenafine is available for topical administration in 1% cream formulation. It
has shown to have superior antifungal activity in tinea pedis, corporis, and cruris compared with topical clotrimazole
and terbinafine. It also has proved to be effective in seborrheic dermatitis caused by
Malassezia Sp.
Our experience dermatophytoses treated with topical Butenafine, a clinical and mycological cure was achieved
in 19/20 cases (95%) with no adverse reactions.
REFERENCES
McNeely W, Spencer CM. Butenafine. Drugs 1998; 55: 405-412.
Mingeot-Leclercq MP, Gallet X, Flore Ch, Bambeke F, Peuvot J, Brasseur R. Experimental and Conformational Analyses of Interactions between Butenafine and Lipids. Antimicrob Agents Chemother 2001; 45: 3347-3354.
Syed TA, Maibach HI. Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother 2000; 1: 467-473.
Arika T, Yokoo M, Yamaguchi H. Topical Treatment with Butenafine Significantly Lowers Relapse Rate in an Interdigital Tinea Pedis Model in Guinea Pigs. Antimicrob Agents Chemother 1992; 36: 2523-2525.
Odom RB. Update on topical therapy for superficial fungal infections: focus butenafine. J Am Acad Dermatol 1997; 36: S1-2.
Savin R, De Villez RL, Elewski B, Hong S, Jones T, Lowe N et al. One-week therapy with twice-daily butenafine 1% cream versus vehicle in the treatment of tinea pedis: a multicenter, double-blind trial. J Am Acad Dermatol 1997; 36: S15-19.
Del Palacio A, Garau M, Tena D, Sánchez G. Tratamiento antifúngico: nuevos avances en dermatología. Rev Iberoam Micol 1999; 16: 86-91.
Ryder NS, Seidl G, Troke PF. Effect of the antimycotic drug naftifine on growth of and sterol biosynthesis in Candida albicans. Antimicrob Agents Chemother 1984;25: 483-487.
Nahm W, Orengo I, Rosen T. The antifungal agent butenafine manifests anti-inflammatory activity in vivo. J Am Acad Dermatol 1999; 41: 203-206.
Mukherjee PK, Leidich SD, Isham N, Leitner I, Ryder NS, Ghan - noum A. Clinical Trichophyton rubrum strain exhibiting primary resistance to terbinafine. Antimicrob Agents Chemother 2003; 47: 82-86.
Ryder NS, Dupont MC. Inhibition of squalene epoxidase by allylamine antimycotic compounds. Biochem J 1985; 230: 765-770.
Castellano S, La Colla P, Musiu C. Azole antifungal agents related to naftifine and butenafine. Arch Pharm 2000; 333: 162-166.
Salmoiraghi I, Rossi M, Valenti P. Allylamine type xanthone antimycotics. Arch Pharm 1998; 331: 225-227.
Elewski BE. Mechanisms of action of systemic antifungal agents. J Am Acad Dermatol 1993; 28: S28-34.
Nussbaumer P, Dorfstetter G, Grassberger MA, Leitner I, Mein - gassner JG, Thirring K et al. Synthesis and structure-activity relationships of phenyl-substituted bezylamine antimycotics: a novel benzyl-benzylamine antifungal agents for systemic treatment. J Med Chem 1993; 36: 2115-2120.
Morita T, Nozawa Y. Effects of antifungal agents on ergosterol biosynthesis in Candida albicans and Trichophyton mentagrophytes: differential inhibitory site of naphtiomate and miconazol. J Invest Dermatol 1985; 85: 434-437.
Schuster I. The interaction of representative members from two classes of antimycotics – the azoles and the allylamines with cytochromes P-450 in steroidogenic tissues and liver. Xenobiotica 1985; 15: 529-546.
Hiratani T, Asagi Y, Yamaguchi H. Studies on antifungal mechanism of butenafine hydrochloride. Inhibition of squalene epoxidation and damaging of cell membranes in Sprorthrix schenckii cells. Jpn J Med Mycol 1991; 32: 139-149.
Gupta AK. Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett 2002; 7: 1-5.
Gupta AK, Einarson TR, Summerbell RC. An overwiew of topical antifungal therapy in dermatomycoses. A North American perspective. Drugs 1998; 55: 645-674.
Paltauf F, Daum G, Zuder G, Hogenauer G, Schulz G. Squalene and ergosterol biosynthesis in fungi treated with naftifine, a new antimycotic agent. Biochim Biophys Acta 1982; 712: 268-273.
Stuts A. Synthesis and structure-activity correlations within allylamine antimycotics. Ann N Y Acad Sci 1988; 544: 46-62.
Tanuma H, Doi M, Ohta, Abe M, Kume H, Mukai H. Butenafine hydrochloride (Mentax) cream for the treatment of hyperkeratotic type tinea pedis and its transfer into the horny layer, with or without concomitant application of 20% urea ointment (Keratinamin). Mycoses 2001; 44: 287-299.
Iwatani W, Arika T, Yaamaguchi H. Two Mechanisms of Butenafine Action in Candida albicans. Antimicrob Agents Chemother 1993; 4: 785-788.
Bialecki J, Ruzicka J, Attygalle AB. An unprecedented rearrangement in collision-induced mass spectrometric fragmentation of protonated benzylamines. J Mass Spectrom 2006; 41: 1195-1204.
Kyle AA, Dahl MV. Topical therapy for fungal infections. Am J Clin Dermatol 2004; 5: 443-451.
Tschen E, Elewski B, Gorsulowsky DC, Pariser DM. Treatment of interdigital tinea pedis with a 4- week once-daily regimen of butenafine hydrochloride 1% cream. J Am Acad Dermatol 1997; 36: S9-14.
Arika T, Yokoo M, Hase T, Maeda T, Amemiya K, Yamaguchi H. Effects of butenafine hydrochloride, a new benzylamine derivative, on experimental dermatophytosis in guinea pigs. Atimicrob Agents Chemother 1990; 34: 2250-2253.
Rubin AI, Bagheri B, Scher RK. Six Novel Antimycotics. Am J Clin Dermato 2002; 2: 71-81.
Gupta AK, Yokou M, Arika T, Bucks D. Evaluation of the in vitro and in vivo efficacy of butenafine hydrochloride cream 1% against Malassezia furfur species and seborrheic dermatitis. J Dermatol Treat 2000; 11: 79-83.
Kokjohn K, Bradley M, Griffiths B, Ghannoum M. Evaluation of in vitro of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria. Inter J Dermatol 2003; 42: 11-17.
Nimura K, Niwano Y, Ishiduka S, Fukumoto R. Comparison of in vitro antifungal activities of topical antimycotics launched in 1990s in Japan. Int J Antimicrob Agents 2001; 18: 173-178.
Singal A, Pandhi D, Agrawal S, Shukla D. Comparative efficacy of topical 1% butenafine and 1% clotrimazole in tinea cruris and tinea corporis: A randomized, double-blind trial. Journal of Dermatological Treatment 2005; 16: 331-335.
Syed T, Hadi SM, Qureshi ZA, Ali SM, Ahmad SA. Butenafine 1% versus Terbinafine 1% in Cream for the Treatment of Tinea Pedis. A placebo-Con tro - lled, Double-Blind, Comparative Study. Clin Drug Invest 2000; 19: 393-397.
Zaias N, Berman B, Cordero CN, Hernandez A, Jacobson C, Millikan L et al. Efficacy of a 1-week, once-daily regimen of terbinafine 1% cream in the treatment of tinea cruris and tinea corporis. J Am Acad Dermatol 1993; 29: 646-648.
Gupta AK, Nicol K, Batra R. Role of antifungal agents in the treatment of seborrheic dermatitis. Am J Clin Dermatol 2004; 5: 417-422.
Lesher JL, Babel DE, Stewart DO, Jones TM. Butenafine 1% cream in the treatment of tinea cruris: a multicenter, vehicle-controlled, double-blind trial. J Am Acad Dermatol 1997; 36: S20-24.
Noguchi H, Hiruma M, Kawada A. Effectiveness of treatment of severe tinea pedis with 1% terbinafine cream in members of the Japanese Self-Defense Forces. Mycoses 2004; 7: 479-484.
Syed TA, Qureshi ZA, Ali SM, Ahmad S, Ahmad SA. Treatment of toenail onychomycosis with 2% butenafine and 5% Malaleuca alternifolia (tea tree) oil in cream. Trop Med Int Health 1999; 4: 284-287.
Syed TA, Ahmadpour OA, Ahmad SA. Management of toenail onychomycosis with 2% butenafine and 20% urea cream: a placebo-controlled, double-blind study. J Dermatol 1998; 25: 648-652.
Saple DG, Amar AK, Ravichandran G, Korde KM, Desai A. Efficacy and safety of butenafine in superficial dermatophytes (tinea pedis, tinea cruris, tinea corporis). J Indian Med Assoc 2001; 99: 274-275.
Reyes AB, Beutner K, Cullen SI, Rosen T, Shupack JL, Weinstein MB. Butenafine, a fungicidal benzylamine derivative, used once daily for the treatment of interdigital tinea pedis. Int J Dermatol 1997; 37: 450-453.
Greer DL, Weiss J, Rodríguez DA, Hebert AA, Swinehart JM. A randomized trial to assess once-daily topical treatmento fo tinea corporis with butenafine, a new antifungal agent. J Am Acad Dermatol 1997; 37: 231-235.
Nadalo D, Montoya C, Hunter-Smith D. What is the best way to treat tinea cruris? J Fam Pract 2006; 55: 256-258.
Berman B, Ellis C, Leyden J, Lowe N, Savin R, Shupack J et al. Efficacy of a 1-week, twice-daily regimen of terbinafine 1% cream in the treatment of interdigital tinea pedis: results of placebo-controlled, double-blind, multicenter trials. J Am Acad Dermatol 1992; 26: 956-60.
Tsuyuki S, Ito M, Unno. Clinical usefulness of butenafine hydrochloride (KP-363) on T. Pedis; comparative study with clotrimazole. Acta Dermatol 1990; 85: 299-306.
Gao PH, Cao YB, Xu Z, Zhang JD, Zhang WN, Wang Y. In vitro antifungal activity of ZJ-522, a new triazole restructured from fluconazole and butenafine, against clinically important fungi in comparison with fluconazole and butenafine. Biol Pharm Bull 2005; 28: 1414-1417.