Luliconazole
Off-white solid powder
Inhibitors/Agonists
Luliconazole is an azole antifungal drug. As a 1% topical cream, luliconazole is indicated for the treatment of athlete's foot, jock itch, and ringworm caused by Trichophyton rubrum and Epidermophyton floccosum. Luliconazole is an antifungal that belongs to the azole class. Although the exact mechanism of action against dermatophytes is unknown, luliconazole appears to inhibit ergosterol synthesis by inhibiting the enzyme lanosterol demethylase. Inhibition of this enzyme's activity by azoles results in decreased amounts of ergosterol, a constituent of fungal cell membranes, and a corresponding accumulation of lanosterol. (copies from http://www.rxlist.com/luzu-drug/clinical-pharmacology.htm).
354.3 g/mol
Formulation:
354.3 g/mol
Source:
Usage:
Luliconazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-274430
CAS Number: 187164-19-8
Molecular Formula: C14H9Cl2N3S2
Molecular Weight: 354.3 g/mol
| CAS Number | 187164-19-8 |
|---|---|
| Product Name | Luliconazole |
| Molecular Formula | C14H9Cl2N3S2 |
| Molecular Weight | 354.3 g/mol |
| Appearance | Off-white solid powder |
| 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 |
| InChI Key | YTAOBBFIOAEMLL-REQDGWNSSA-N |
| Isomeric SMILES | C1[C@H](S/C(=C(\C#N)/N2C=CN=C2)/S1)C3=C(C=C(C=C3)Cl)Cl |
| IUPAC Name | (2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile |
| Canonical SMILES | C1C(SC(=C(C#N)N2C=CN=C2)S1)C3=C(C=C(C=C3)Cl)Cl |
| Description | Luliconazole is an azole antifungal drug. As a 1% topical cream, luliconazole is indicated for the treatment of athlete's foot, jock itch, and ringworm caused by Trichophyton rubrum and Epidermophyton floccosum. Luliconazole is an antifungal that belongs to the azole class. Although the exact mechanism of action against dermatophytes is unknown, luliconazole appears to inhibit ergosterol synthesis by inhibiting the enzyme lanosterol demethylase. Inhibition of this enzyme's activity by azoles results in decreased amounts of ergosterol, a constituent of fungal cell membranes, and a corresponding accumulation of lanosterol. (copies from http://www.rxlist.com/luzu-drug/clinical-pharmacology.htm). |
| Other CAS Number | 187164-19-8 |
| Shelf Life | >2 years if stored properly |
| SMILES | C1C(SC(=C(C#N)N2C=CN=C2)S1)C3=C(C=C(C=C3)Cl)Cl |
| Solubility | Soluble in DMSO. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | (2E)-((4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)(1H-imidazol-1-yl)acetonitrile 4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile Lulicon luliconazole NND 502 NND-502 NND502 |
| Reference | 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. |
| PubChem Compound | Luliconazole |
| Last Modified | Mar 14 2022 |