Luliconazole

  • CAT Number: A000163
  • CAS Number: 187164-19-8
  • Molecular Formula: C14H9Cl2N3S2
  • Molecular Weight: 354.28
  • Purity: ≥95%
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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).

Catalog Number A000163
CAS Number 187164-19-8
Molecular Formula

C14H9Cl2N3S2

Purity 95%
Target Antibiotic
Solubility >17.7mg/mL in DMSO
Storage Store at -20°C
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
InChIKey YTAOBBFIOAEMLL-REQDGWNSSA-N
SMILES C1C(SC(=C(C#N)N2C=CN=C2)S1)C3=C(C=C(C=C3)Cl)Cl
Reference

1: Shokoohi GR, Badali H, Mirhendi H, Ansari S, Rezaei-Matehkolaei A, Ahmadi B,
Vaezi A, Alshahni MM, Makimura K. In Vitro Activities of Luliconazole,
Lanoconazole, and Efinaconazole Compared with Those of Five Antifungal Drugs
against Melanized Fungi and Relatives. Antimicrob Agents Chemother. 2017 Oct
24;61(11). pii: e00635-17. doi: 10.1128/AAC.00635-17. Print 2017 Nov. PubMed
PMID: 28848012; PubMed Central PMCID: PMC5655049.
<br>

2: Zargaran M, Taghipour S, Kiasat N, Aboualigalehdari E, Rezaei-Matehkolaei A,
Zarei Mahmoudabadi A, Shamsizadeh F. Luliconazole, an alternative antifungal
agent against Aspergillus terreus. J Mycol Med. 2017 Sep;27(3):351-356. doi:
10.1016/j.mycmed.2017.04.011. Epub 2017 May 5. PubMed PMID: 28483449.
<br>

3: Watanabe S, Kishida H, Okubo A. Efficacy and safety of luliconazole 5% nail
solution for the treatment of onychomycosis: A multicenter, double-blind,
randomized phase III study. J Dermatol. 2017 Jul;44(7):753-759. doi:
10.1111/1346-8138.13816. Epub 2017 Mar 23. PubMed PMID: 28332720.
<br>

4: Zhou BR, Lu Y, Permatasari F, Huang H, Li J, Liu J, Zhang JA, Luo D, Xu Y. The
efficacy of fractional carbon dioxide (CO2) laser combined with luliconazole 1%
cream for the treatment of onychomycosis: A randomized, controlled trial.
Medicine (Baltimore). 2016 Nov;95(44):e5141. PubMed PMID: 27858846; PubMed
Central PMCID: PMC5591094.
<br>

5: Abastabar M, Rahimi N, Meis JF, Aslani N, Khodavaisy S, Nabili M,
Rezaei-Matehkolaei A, Makimura K, Badali H. Potent Activities of Novel Imidazoles
Lanoconazole and Luliconazole against a Collection of Azole-Resistant and
-Susceptible Aspergillus fumigatus Strains. Antimicrob Agents Chemother. 2016 Oct
21;60(11):6916-6919. doi: 10.1128/AAC.01193-16. Print 2016 Nov. PubMed PMID:
27572389; PubMed Central PMCID: PMC5075107.
<br>

6: Sarkar S, Sengupta D, Basak S, Damji SA, Shukla DK, Anurag D. Comparative
assessment of the efficacy of topical ketoconazole and topical luliconazole in
cases of pityriasis versicolor at a tertiary care hospital in eastern India: A
prospective, open, randomized controlled trial. Indian Dermatol Online J. 2016
Jul-Aug;7(4):335-6. doi: 10.4103/2229-5178.185471. PubMed PMID: 27559523; PubMed
Central PMCID: PMC4976428.
<br>

7: Saunders J, Maki K, Koski R, Nybo SE. Tavaborole, Efinaconazole, and
Luliconazole: Three New Antimycotic Agents for the Treatment of Dermatophytic
Fungi. J Pharm Pract. 2016 Aug 3. pii: 0897190016660487. [Epub ahead of print]
PubMed PMID: 27488125.
<br>

8: Baghi N, Shokohi T, Badali H, Makimura K, Rezaei-Matehkolaei A, Abdollahi M,
Didehdar M, Haghani I, Abastabar M. In vitro activity of new azoles luliconazole
and lanoconazole compared with ten other antifungal drugs against clinical
dermatophyte isolates. Med Mycol. 2016 Oct 1;54(7):757-63. doi:
10.1093/mmy/myw016. Epub 2016 Apr 26. PubMed PMID: 27118804.
<br>

9: Hasuko M, Toga T, Tsunemitsu T, Matsumoto T, Koga H, Hirano H, Tsuboi R.
[Affinity of Luliconazole to Keratin Prepared from Healthy Human Nailand Porcine
Hoof]. Med Mycol J. 2016;57(1):J7-12. doi: 10.3314/mmj.57.J7. Japanese. PubMed
PMID: 26936352.
<br>

10: Shimamura T, Miyamae A, Arai M, Minemura A, Nozawa A, Kubota N. [Distribution
of Luliconazole in Nail Plate by In Vitro Permeation and Efficacy by Zone of
Inhibition Test after Treatment of Luliconazole Nail Solution]. Med Mycol J.
2016;57(1):J19-25. doi: 10.3314/mmj.57.J19. Japanese. PubMed PMID: 26936348.

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