Generic placeholder image

Current Bioactive Compounds

Author(s): Arun K. Mishra*, Arvind Kumar, Harpreet Singh, Shweta Verma, Jagdish K. Sahu and Amrita Mishra

DOI: 10.2174/1573407214666180717111419

DownloadDownload PDF Flyer Cite As
Chemistry and Pharmacology of Luliconazole (Imidazole Derivative): A Novel Bioactive Compound to Treat Fungal Infection-A Mini Review

Page: [602 - 609] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

Background: Currently, ringworm treatment drugs include two major categories: first, propylene amine drugs, such as terbinafine, butenafine and naftifine, which exert their bactericidal effects through inhibiting squalene cyclase, causing the lack of ergosterol and accumulation of squalene. The second category of imidazole drugs includes miconazole, econazole, clotrimazole, ketoconazole and bifonazole.

Mechanism: These synthetic antifungal agents exhibits their action by inhibiting the lanosterol 14α- demethylation activity of fungal cell, leading to the prevention of the ergosterol synthesis of cell membrane, changing the cell membrane permeability, and resulting in the loss of important intracellular fungal material and causing fungal death.

Applications: At present, Imidazole antifungal agents are commonly used drugs in clinical treatment of ringworm with extensive clinical applications.

Conclusion: The present review covers the chemistry and detailed pharmacology aspects of luliconazole.

Keywords: Imidazole derivatives, fungal infection, cutaneous mycoses, luliconazole, lanosteroldemethylase, ailments.

Graphical Abstract

[1]
Uchida, K.; Nishiyama, Y.; Yamaguchi, H. In vitro antifungal activity of luliconazole (NND-502), a novel imidazole antifungal agent. J. Infect. Chemother., 2004, 10(4), 216-219.
[http://dx.doi.org/10.1007/s10156-004-0327-1] [PMID: 15365862]
[2]
Scher, R.K.; Nakamura, N.; Tavakkol, A. Luliconazole: A review of a new antifungal agent for the topical treatment of onychomycosis. Mycoses, 2014, 57(7), 389-393.
[http://dx.doi.org/10.1111/myc.12168] [PMID: 24621346]
[3]
Sahoo, A.K.; Mahajan, R. Management of Tinea corporis, Tinea cruris, and Tinea pedis: A comprehensive review. Indian Dermatol. Online J., 2016, 7(2), 77-86.
[http://dx.doi.org/10.4103/2229-5178.178099] [PMID: 27057486]
[4]
Humera, Q.F.A.; Sultana, Q.; Siddiqui, M.A.W. Epidemiology of dermatophytic infections with evaluation of efficacy and safety of luliconazole cream 1% versus miconazole 2% cream- A randomized two-group study. Int. J. Bio. Pharm. Res., 2015, 6(5), 359-363.
[5]
Watanabe, S.; Takahashi, H.; Nishikawa, T.; Takiuchi, I.; Higashi, N.; Nishimoto, K.; Kagawa, S.; Yamaguchi, H.; Ogawa, H. A comparative clinical study between 2 weeks of luliconazole 1% cream treatment and 4 weeks of bifonazole 1% cream treatment for Tinea pedis. Mycoses, 2006, 49(3), 236-241.
[http://dx.doi.org/10.1111/j.1439-0507.2006.01218.x] [PMID: 16681817]
[6]
Koga, H.; Nanjoh, Y.; Kaneda, H.; Yamaguchi, H.; Tsuboi, R. Short-term therapy with luliconazole, a novel topical antifungal imidazole, in guinea pig models of Tinea corporis and Tinea pedis. Antimicrob. Agents Chemother., 2012, 56(6), 3138-3143.
[http://dx.doi.org/10.1128/AAC.05255-11] [PMID: 22391525]
[7]
Jones, T.; Tavakkol, A. Safety and tolerability of luliconazole solution 10-percent in patients with moderate to severe distal subungual onychomycosis. Antimicrob. Agents Chemother., 2013, 57(6), 2684-2689.
[http://dx.doi.org/10.1128/AAC.02370-12] [PMID: 23545529]
[8]
Niwano, Y.; Ohmi, T.; Seo, A.; Kodama, H.; Kanai, K. Lanoconazole and its relative compounds: Progressive antifungal imidazole with a ketene dithioacctal structure. Recent Res. Devel. Antimicrob. Agents Chemother, 2000, 4, 81-102.
[9]
https://www.pharmacodia.com/web/drug/1_90.html
[10]
Khanna, D.; Bharti, S. Luliconazole for the treatment of fungal infections: An evidence-based review. Core Evid., 2014, 9, 113-124.
[http://dx.doi.org/10.2147/CE.S49629] [PMID: 25285056]
[11]
Uchida, K.; Nishiyama, Y.; Tanaka, T.; Yamaguchi, H. In vitro activity of novel imidazole antifungal agent NND-502 against Malassezia species. Int. J. Antimicrob. Agents, 2003, 21(3), 234-238.
[http://dx.doi.org/10.1016/S0924-8579(02)00362-X] [PMID: 12636984]
[12]
Minnebruggen, G.V.; François, I.E.J.A.; Cammue, B.P.A.; Thevissen, K.; Vroome, V.; Borgers, M.; Shroot, B. A general overview on past, present and future antimycotics. The Open Mycol. J., 2010, 4, 22-32.
[13]
Jerajani, H.; Janaki, C.; Kumar, S.; Phiske, M. Comparative assessment of the efficacy and safety of sertaconazole (2%) cream versus terbinafine cream (1%) versus luliconazole (1%) cream in patients with dermatophytoses: A pilot study. Indian J. Dermatol., 2013, 58(1), 34-38.
[http://dx.doi.org/10.4103/0019-5154.105284] [PMID: 23372210]
[14]
Ghannoum, M.A.; Long, L.; Kim, H.G.; Cirino, A.J.; Miller, A.R.; Mallefet, P. Efficacy of terbinafine compared to lanoconazole and luliconazole in the topical treatment of dermatophytosis in a guinea pig model. Med. Mycol., 2010, 48(3), 491-497.
[http://dx.doi.org/10.3109/13693780903373811] [PMID: 20370362]
[15]
Gupta, A.K.; Daigle, D. A critical appraisal of once-daily topical luliconazole for the treatment of superficial fungal infections. Infect. Drug Resist., 2016, 9, 1-6.
[http://dx.doi.org/10.2147/IDR.S61998] [PMID: 26848272]
[16]
Koga, H.; Nanjoh, Y.; Makimura, K.; Tsuboi, R. In vitro antifungal activities of luliconazole, a new topical imidazole. Med. Mycol., 2009, 47(6), 640-647.
[http://dx.doi.org/10.1080/13693780802541518] [PMID: 19115136]
[17]
Koga, H.; Tsuji, Y.; Inoue, K.; Kanai, K.; Majima, T.; Kasai, T.; Uchida, K.; Yamaguchi, H. In vitro antifungal activity of luliconazole against clinical isolates from patients with dermatomycoses. J. Infect. Chemother., 2006, 12(3), 163-165.
[http://dx.doi.org/10.1007/s10156-006-0440-4] [PMID: 16826352]
[18]
Selvan, A.T.; Girisha, G.; Bhaskar, V.; Suthakaran, R. Comparative evaluation of newer topical antifungal agents in the treatment of superficial fungal infections (Tinea or dermatophytic). Int. Res. J. Pharm, 2013, 4, 224-228.
[http://dx.doi.org/10.7897/2230-8407.04651]
[19]
Holt, R.J. Topical pharmacology of imidazole antifungals. J. Cutan. Pathol., 1976, 3(1), 45-59.
[http://dx.doi.org/10.1111/j.1600-0560.1976.tb00846.x] [PMID: 945306]
[20]
De Beule, K.; Van Gestel, J. Pharmacology of itraconazole. Drugs, 2001, 61(1)(Suppl. 1), 27-37.
[http://dx.doi.org/10.2165/00003495-200161001-00003] [PMID: 11219548]
[21]
Nagappan, V.; Deresinski, S. Reviews of anti-infective agents: Posaconazole: A broad-spectrum triazole antifungal agent. Clin. Infect. Dis., 2007, 45(12), 1610-1617.
[http://dx.doi.org/10.1086/523576] [PMID: 18190324]
[22]
Chang, M.; Chagan, L. Posaconazole (Noxafil), an Extended-spectrum oral triazole antifungal agent. Pharm. Ther., 2008, 33(7), 391-426.
[23]
Casalinuovo, I.A.; Di Francesco, P.; Garaci, E. Fluconazole resistance in Candida albicans: A review of mechanisms. Eur. Rev. Med. Pharmacol. Sci., 2004, 8(2), 69-77.
[PMID: 15267120]
[24]
Charlier, C.; Hart, E.; Lefort, A.; Ribaud, P.; Dromer, F.; Denning, D.W.; Lortholary, O. Fluconazole for the management of invasive candidiasis: Where do we stand after 15 years? J. Antimicrob. Chemother., 2006, 57(3), 384-410.
[http://dx.doi.org/10.1093/jac/dki473] [PMID: 16449304]
[25]
Feldman, D. Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis. Endocr. Rev., 1986, 7(4), 409-420.
[http://dx.doi.org/10.1210/edrv-7-4-409] [PMID: 3536461]
[26]
Lipner, S.R.; Scher, R.K. Efinaconazole in the treatment of onychomycosis. Infect. Drug Resist., 2015, 8, 163-172.
[http://dx.doi.org/10.2147/IDR.S69596] [PMID: 26082652]
[27]
Mallu, U.R.; Reddy, K.H.; Bobbarala, V.; Penumajji, S. Determination of beclomethasone dipropionate, clotrimazole, chloramphenicol and lidocaine in pharmaceutical formulations using a novel RP-HPLC method. Int. J. Pharm. Bio Sci., 2011, 2(3), 453-462.
[28]
Dayyih, W.A.; Saadi, N.A.; Hamad, A.; Mallaha, E.; Matalka, K.; Arafat, T. Development and validation of HPLC method for some azoles in pharmaceutical preparation. Int. J. Pharm. Sci. Res., 2012, 3(10), 3686-3692.
[29]
Ramachandran, R.; Rani, M.; Senthan, S.; Jeong, Y.T.; Kabilan, S. Synthesis, spectral, crystal structure and in vitro antimicrobial evaluation of imidazole/benzotriazole substituted piperidin-4-one derivatives. Eur. J. Med. Chem., 2011, 46(5), 1926-1934.
[http://dx.doi.org/10.1016/j.ejmech.2011.02.036] [PMID: 21397368]
[30]
Husain, A.; Drabu, S.; Kumar, N.; Alam, M.M.; Bawa, S. Synthesis and biological evaluation of di- and tri-substituted imidazoles as safer anti-inflammatory-antifungal agents. J. Pharm. Bioallied Sci., 2013, 5(2), 154-161.
[http://dx.doi.org/10.4103/0975-7406.111822] [PMID: 23833522]
[31]
Niwano, Y.; Kuzuhara, N.; Kodama, H.; Yoshida, M.; Miyazaki, T.; Yamaguchi, H. In vitro and in vivo antidermatophyte activities of NND-502, a novel optically active imidazole antimycotic agent. Antimicrob. Agents Chemother., 1998, 42(4), 967-970.
[http://dx.doi.org/10.1128/AAC.42.4.967] [PMID: 9559824]
[32]
Saha, A.K.; Liu, L.; Simoneaux, R.L.; Kukla, M.J.; Marichal, P.; Odds, F. Novel antifungals based on 4-substituted imidazole: A combinatorial chemistry approach to lead discovery and optimization. Bioorg. Med. Chem. Lett., 2000, 10(19), 2175-2178.
[http://dx.doi.org/10.1016/S0960-894X(00)00445-5] [PMID: 11012023]
[33]
Agarwal, V.; Kumar, M.; Pathak, K. Defining the Properties of pH -sensitive polymeric micellar ocular delivery system of miconazole nitrate for the management of fungal endophthalmitis. Pharm. Nanotechnol., 2014, 2(3), 157-166.
[http://dx.doi.org/10.2174/2211738502666141112220729]
[34]
Delgado, J.N.; Remers, W.A. Wilson and Gisvold’s textbook oforganic medicinal and pharmaceutical chemistry, 11th ed; Lippincott-Williams and Wilkins, 1998.
[35]
Setzu, M.G.; Stefancich, G.; La Colla, P.; Castellano, S. Synthesis and antifungal properties of N-[(1,1′-biphenyl)-4-ylmethyl]-1H-imidazol-1-amine derivatives. Farmaco, 2002, 57(12), 1015-1018.
[http://dx.doi.org/10.1016/S0014-827X(02)01294-6] [PMID: 12564477]
[36]
Emami, S.; Foroumadi, A.; Falahati, M.; Lotfali, E.; Rajabalian, S.; Ebrahimi, S.A.; Farahyar, S.; Shafiee, A. 2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents. Bioorg. Med. Chem. Lett., 2008, 18(1), 141-146.
[http://dx.doi.org/10.1016/j.bmcl.2007.10.111] [PMID: 18032039]
[37]
Walker, K.A.M.; Braemer, A.C.; Hitt, S.; Jones, R.E.; Matthews, T.R. 1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent. J. Med. Chem., 1978, 21(8), 840-843.
[http://dx.doi.org/10.1021/jm00206a028] [PMID: 357722]
[38]
Ogata, M.; Matsumoto, H.; Hamada, Y.; Takehara, M.; Tawara, K. 1-[1-[2-[(3-Chlorobenzyl)oxy]phenyl]vinyl]-1H-imidazole hydrochloride, a new potent antifungal agent. J. Med. Chem., 1983, 26(5), 768-770.
[http://dx.doi.org/10.1021/jm00359a026] [PMID: 6842519]
[39]
Clissold, S.P.; Heel, R.C. Tioconazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. Drugs, 1986, 31(1), 29-51.
[http://dx.doi.org/10.2165/00003495-198631010-00003] [PMID: 3510114]
[40]
Mahmoudabadi, A.Z.; Drucker, D.B. Effect of Amphotericin B, nystatin and miconazole on the polar lipids of C. albicans and C. dubliniensis. Indian J. Pharm., 2006, 38(6), 423-426.
[http://dx.doi.org/10.4103/0253-7613.28210]
[41]
Croxtall, J.D.; Plosker, G.L. Sertaconazole: A review of its use in the management of superficial mycoses in dermatology and gynaecology. Drugs, 2009, 69(3), 339-359.
[http://dx.doi.org/10.2165/00003495-200969030-00009] [PMID: 19275277]
[42]
Niwano, Y.; Ohmi, T.; Seo, A.; Kodama, H.; Koga, H.; Sakai, A. Lanoconazole and its related optically active compound NND-502: Novel antifungal imidazoles with a ketene dithioacetal structure. Curr. Med. Anti Infect. Agents, 2003, 2, 147-160.
[http://dx.doi.org/10.2174/1568012033483097]
[43]
Singh, K.; Sood, S.; Bala, R.; Sangwan, V.; Singh, N. Iodine mediated synthesis of thiabendazole derivatives and their antimicrobial evaluation. Curr. Bioact. Compd., 2018, 13, 1-5.
[http://dx.doi.org/10.2174/1573407213666170407160418]
[44]
Saha, A.K.; Liu, L.; Marichal, P.; Odds, F. Novel antifungals based on 4-substituted imidazole: solid-phase synthesis of substituted aryl sulfonamides towards optimization of in vitro activity. Bioorg. Med. Chem. Lett., 2000, 10(24), 2735-2739.
[http://dx.doi.org/10.1016/S0960-894X(00)00551-5] [PMID: 11133080]
[45]
De Luca, L. Naturally occurring and synthetic imidazoles: Their chemistry and their biological activities. Curr. Med. Chem., 2006, 13(1), 1-23.
[http://dx.doi.org/10.2174/092986709787002826] [PMID: 16457636]
[46]
Fontana, G. Current bioactive azole-containing natural products. Curr. Bioact. Compd., 2010, 6(4), 284-308.
[http://dx.doi.org/10.2174/157340710793237290]
[47]
Saxena, S.; Chhibber, M.; Singh, I.P. Fungal bioactive compounds in pharmaceutical research and development. Curr. Bioact. Compd., 2018, 14, 11-18.
[http://dx.doi.org/10.2174/1573407214666180420092631]
[48]
https://preview.ncbi.nlm.nih.gov/pubmedhealth/PMHT0021843/?report=details [Accessed November 11 2017].