Synonym
NND502; NND 502; NND502; PR2699; PR 2699; PR2699; Luzu; Lulicon; Luliconazole.
IUPAC/Chemical Name
(2E)-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene](1H-imidazol-1-yl)acetonitrile
InChi Key
YTAOBBFIOAEMLL-REQDGWNSSA-N
InChi Code
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
SMILES Code
N#C/C(N1C=CN=C1)=C2SC[C@@H](C3=CC=C(Cl)C=C3Cl)S/2
Appearance
Off-white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Luliconazole (NND 502) is a topical antifungal imidazole antibiotic with broad-spectrum and potent antifungal activity
In vitro activity:
The in vitro activities of luliconazole, amorolfine, ciclopirox, and terbinafine were determined against 320 dermatophyte isolates from large toenails of onychomycosis patients enrolled into an ongoing phase 2b/3 clinical study. Luliconazole had potent activity against the dermatophyte isolates collected from patients with onychomycosis in this trial. As shown in Table 1, the MICs for this agent against all isolates ranged from 0.00012 to 0.0025 μg/ml, compared to 0.008 to 0.5 μg/ml for amorolfine, 0.03 to 1 μg/ml for ciclopirox, and 0.004 to 0.25 μg/ml for terbinafine. The luliconazole GM MIC against all isolates was 0.00022 μg/ml, while those of the other agents were as follows: amorolfine, 0.0867 μg/ml; ciclopirox, 0.3107 μg/ml; and terbinafine, 0.0194 μg/ml. The MIC50 and MIC90 values of luliconazole were 0.00025 and 0.0005 μg/ml, respectively, and those of the other agents ranged from 0.015 to 0.25 μg/ml and 0.03 to 0.5 μg/ml, respectively. When the data were separated by species, similar results were observed, as the potency of luliconazole was maintained regardless of the species. As observed against all isolates combined, the MIC50 and MIC90 values for luliconazole against either T. rubrum or T. mentagrophytes isolates were 7 to 10 dilutions lower than those observed with the other antifungals. Luliconazole demonstrated potent activity against the single isolates of T. tonsurans and E. floccosum (MIC, 0.000125 μg/ml against each). These data suggest that luliconazole may be a suitable option for the treatment of this disease.
Antimicrob Agents Chemother. 2014 Jun; 58(6): 3553–3555. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4068440/
In vivo activity:
The present study was undertaken to investigate the clinical benefit of short-term therapy with luliconazole cream in guinea pig models of tinea corporis and tinea pedis induced with Trichophyton mentagrophytes. Luliconazole cream prepared at various concentrations improved skin lesions in a dose-dependent manner. Compared to the nontreated group and/or the cream base group, there was a statistically significant improvement in lesions treated with 0.02% LLCZ cream, and 0.1% LLCZ cream was comparable in efficacy to the 1% BFZ cream. The LLCZ cream eliminated the fungi in a dose-dependent manner, and statistically significant differences in fungal burden were observed even after treatment with a concentration of 0.02% LLCZ compared to the nontreated and/or cream base group. The LLCZ cream completely cured the mycological infection at concentrations of 0.5% and above. The 1% LLCZ cream significantly improved the skin lesions in the 4-day treatment and 8-day treatment groups compared to those in controls, and the efficacy ratings were similar to those for the 1% TRB cream groups (4- and 8-day treatments). he MICs of LLCZ against T. mentagrophytes TIMM1189 and TIMM2789 were 4 and 8 times lower, respectively, than that of TRB and 250 and 2,000 times lower, respectively, than that of BFZ. In addition, LLCZ has been shown to have preferable pharmacokinetic properties in the skin compared to TRB.
Antimicrob Agents Chemother. 2012 Jun; 56(6): 3138–3143. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3370799/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
47.0 |
132.66 |
| Ethanol |
8.0 |
22.58 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
354.28
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Nagashima H, Koike N, Yoshida K, Saya H, Sampetrean O. Antifungal Agent Luliconazole Inhibits the Growth of Mouse Gliomainitiating Cells in Brain Explants. Keio J Med. 2020 Dec 25;69(4):97-104. doi: 10.2302/kjm.2020-0001-OA. Epub 2020 Jul 31. PMID: 32741855. 2. Wiederhold NP, Fothergill AW, McCarthy DI, Tavakkol A. Luliconazole demonstrates potent in vitro activity against dermatophytes recovered from patients with onychomycosis. Antimicrob Agents Chemother. 2014 Jun;58(6):3553-5. doi: 10.1128/AAC.02706-13. Epub 2014 Apr 7. PMID: 24709260; PMCID: PMC4068440.
3. 1. 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 Jun;56(6):3138-43. doi: 10.1128/AAC.05255-11. Epub 2012 Mar 5. PMID: 22391525; PMCID: PMC3370799.
4. Shimamura T, Hasegawa N, Kubota N. [Antifungal Activity of Luliconazole Nail Solution on in vitro and in vivo Onychomycosis Model]. Med Mycol J. 2016;57(1):J13-8. Japanese. doi: 10.3314/mmj.57.J13. PMID: 26936347.
In vitro protocol:
1. Nagashima H, Koike N, Yoshida K, Saya H, Sampetrean O. Antifungal Agent Luliconazole Inhibits the Growth of Mouse Gliomainitiating Cells in Brain Explants. Keio J Med. 2020 Dec 25;69(4):97-104. doi: 10.2302/kjm.2020-0001-OA. Epub 2020 Jul 31. PMID: 32741855. 2. Wiederhold NP, Fothergill AW, McCarthy DI, Tavakkol A. Luliconazole demonstrates potent in vitro activity against dermatophytes recovered from patients with onychomycosis. Antimicrob Agents Chemother. 2014 Jun;58(6):3553-5. doi: 10.1128/AAC.02706-13. Epub 2014 Apr 7. PMID: 24709260; PMCID: PMC4068440.
In vivo protocol:
1. 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 Jun;56(6):3138-43. doi: 10.1128/AAC.05255-11. Epub 2012 Mar 5. PMID: 22391525; PMCID: PMC3370799.
2. Shimamura T, Hasegawa N, Kubota N. [Antifungal Activity of Luliconazole Nail Solution on in vitro and in vivo Onychomycosis Model]. Med Mycol J. 2016;57(1):J13-8. Japanese. doi: 10.3314/mmj.57.J13. PMID: 26936347.
1: Luliconazole cream (Luzu) for tinea infections. Med Lett Drugs Ther. 2014 Jun 23;56(1445):50-1. PubMed PMID: 24956308.
2: Gupta AK, Cvetković D, Abramovits W, Vincent KD. LUZU (luliconazole) 1% cream. Skinmed. 2014 Mar-Apr;12(2):90-3. PubMed PMID: 24933846.
3: Wiederhold NP, Fothergill AW, McCarthy DI, Tavakkol A. Luliconazole Demonstrates Potent In Vitro Activity against Dermatophytes Recovered from Patients with Onychomycosis. Antimicrob Agents Chemother. 2014 Jun;58(6):3553-3555. Epub 2014 Apr 7. PubMed PMID: 24709260.
4: Scher RK, Nakamura N, Tavakkol A. Luliconazole: a review of a new antifungal agent for the topical treatment of onychomycosis. Mycoses. 2014 Jul;57(7):389-93. doi: 10.1111/myc.12168. Epub 2014 Mar 12. PubMed PMID: 24621346.
5: Jones TM, Jarratt MT, Mendez-Moguel I, Paz N, Grekin SK, Cognata Smith C, Kaur M. A randomized, multicenter, double-blind, vehicle-controlled study evaluating the efficacy and safety of luliconazole cream 1% once daily for 7 days in patients aged ≥ 12 years with tinea cruris. J Drugs Dermatol. 2014 Jan;13(1):32-8. PubMed PMID: 24385117.
6: Jarratt M, Jones T, Kempers S, Rich P, Morton K, Nakamura N, Tavakkol A. Luliconazole for the treatment of interdigital tinea pedis: A double-blind, vehicle-controlled study. Cutis. 2013 Apr;91(4):203-10. PubMed PMID: 23763082.
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 Jun;57(6):2684-9. doi: 10.1128/AAC.02370-12. Epub 2013 Apr 1. PubMed PMID: 23545529; PubMed Central PMCID: PMC3716121.
8: 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 Jan;58(1):34-8. doi: 10.4103/0019-5154.105284. PubMed PMID: 23372210; PubMed Central PMCID: PMC3555370.
9: 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 Jun;56(6):3138-43. doi: 10.1128/AAC.05255-11. Epub 2012 Mar 5. PubMed PMID: 22391525; PubMed Central PMCID: PMC3370799.
10: Ghannoum MA, Long L, Kim HG, Cirino AJ, Miller AR, Mallefet P. Efficacy of terbinafine compared to lanoconazole and luliconazole in the topical treatment of dermatophytosis in a guinea pig model. Med Mycol. 2010 May;48(3):491-7. doi: 10.3109/13693780903373811. PubMed PMID: 20370362.
