Luliconazole - CAS 187164-19-8
Catalog number: 187164-19-8
Category: Inhibitor
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Molecular Formula:
C14H9Cl2N3S2
Molecular Weight:
354.28
COA:
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Targets:
Antifungal
Description:
Luliconazole is an azole antifungal indicated for the topical treatment of interdigital tinea pedis.
Purity:
0.98
Synonyms:
NND502; NND 502; NND502; PR2699; PR 2699; PR2699; Luzu; Lulicon; Luliconazole.
MSDS:
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InChIKey:
YTAOBBFIOAEMLL-REQDGWNSSA-N
InChI:
InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1
Canonical SMILES:
C1C(SC(=C(C#N)N2C=CN=C2)S1)C3=C(C=C(C=C3)Cl)Cl
1. Development of drugs based on imidazole and benzimidazole bioactive heterocycles: recent advances and future directions
Monika Gaba • Chander Mohan. Med Chem Res (2016) 25:173–210
Much effort has been made by different pharmaceutical companies toward antifungal therapy that resulted in various drugs containing imidazole such as flutrimazole (Alomar et al., 1995), bifonazole (Bayer AG; Plempel et al., 1983), butoconazole, an outlier having a 1-(phenylbutyl)-imidazole scaffold (Syntex Research Lab-oratories; Fromtling, 1986), croconazole (Shionogi Research Laboratories; Ogata et al., 1983), fenticonazole (Recordati SpA; Tajana et al., 1981), isoconazole (Janssen Pharmaceutica;HernandezMolina et al., 1992), oxiconazole (F. Hoffmann-LaRoche and Siegfried AG; Polak, 1982), sulconazole (Syntex Research; Yoshida et al., 1984), tioconazole (Pfizer; Jevons et al., 1979), luliconazole (Nihon Nohyaku Co., Ltd.; Uchida et al., 2004), omoconazole (Siegfried AG; Thiele et al., 1987, Fromtling, 1988), sertaconazole (Ortiz, 1992; Palacin et al., 2001), neticonazole (Nimura et al., 2001), and eberconazole (designed and investigated by the Wassermann investigation center; Fernandez-Torres et al., 2003) (Fig. 12).
2. In vitro antifungal activity of luliconazole (NND-502), a novel imidazole antifungal agent
Katsuhisa Uchida • Yayoi Nishiyama • Hideyo Yamaguchi. J Infect Chemother (2004) 10:216–219
Luliconazole, with the chemical formula of (R)-(-)-(E)-[4-(2, 4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile and the structure shown in Fig. 1, is a novel optically active antifungal imidazole compound whose preparations of topical use are under clinical trial for treatment of dermatophytosis and other superficial cutaneous fungal infections in Japan. Although luliconazole is structurally related to its predecessor lanoconazole, which has been clinically used for the topical treatment of dermatophytosis as well as of cutaneous candidiasis and malasseziosis in this country, they are chemically different in that the former is an R-enantiomer and the latter a racemic compound consisting of an active R-enantiomer and S-enantiomers. To learn the antifungal potency and spectrum of luliconazole, we studied its in vitro activity against dermatophytes and a variety of causative agents of superficial cutaneous and/or subcutaneous fungal infections in comparison with lanoconazole, bifonazole, and terbinafine, all of which are widely used for the topical treatment of superficial dermatomycoses in Japan.
3. In vitro antifungal activity of luliconazole against clinical isolates from patients with dermatomycoses
Hiroyasu Koga • Yuri Tsuji • Kazuyoshi Inoue. J Infect Chemother (2006) 12:163–165
Luliconazole ((−)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene] (1H-imidazol-1-yl) acetonitrile, Fig. 1), is a novel antifungal drug discovered by Nihon Nohyaku (Tokyo, Japan). The compound was originally screened from optically active compounds related to lanoconazole, a potent antidermatophytic drug available in Japan. Luliconazole possesses a wide spectrum of antifungal activity and is very potent against dermatophytes, both in vitro and in vivo. A cream and a solution of 1% luliconazole were successfully developed for the topical treatment of superficial dermatomycoses (in particular, dermatophytoses), and these products were clinically introduced in Japan in 2005. The present study attempted to support the clinical use of the 1% luliconazole preparations during the clinical trial period of this drug. For this purpose, the in vitro activity of luliconazole against clinical isolates of fungi, obtained from patients with dermatophytosis and cutaneous candidiasis at a dermatological clinic in Japan, were assessed, using lanoconazole, terbinafine, and bifonazole as reference drugs.
4. Direct Extraction of DNA from Positive Transparent Dressing and Swab to Identify Candida albicans Infection in Intertriginous Candidiasis in the Inguinal Region
Daoxian Kang • Yuping Ran • Yaling Dai • Jebina Lama. Mycopathologia (2012) 174:519–521
Therapy for cutaneous candidiasis is dominated by use of topical antifungal agents. Azole antifungal creams (e.g., bifonazole, ketoconazole, neticonazole hydrochloride, lanoconazole, and luliconazole) are most effective, terbinafine hydrochloride less so. It is, therefore, very important to confirm the identity of the pathological agent to enable choice of the most appropriate antifungal drug as quickly as possible. Traditional confirmation of the identity of culture colonies often takes 7–14 days. Molecular biological confirmation by use of the positive transparent dressing and swab can be achieved in 48 h. Subsequent culture confirmation can be used of verify the culture-independent identification.
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CAS 187164-19-8 Luliconazole

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