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Purity: ≥98%
Liranaftate (formerly M-732; Piritetrate; Zefnart) is a thiocarbamate-based inhibitor of squalene epoxidase with fungicidal activities. It inhibits fungal squalene epoxidase, which is an enzyme that plays a key role in the synthesis of sterol, compouds essential for cell membrane integrity. By preventing ergosterol synthesis and causing accumulation of squalene, this agent increases cell membrane permeability, cell leakage and eventually cell lysis. Liranaftate showed excellent fungistatic activity against the conidia of T. rubrum. For each of these agents, the MIC after 14 days of contact was 0.009 g/ml. The liranaftate-induced decrease in the MCC occurred from 9 days onwards; MCC at 14 days was 0.039 g/ml. In time-kill studies, liranaftate showed the greatest decrease to a below detection limit in viable counts of T rubrum. The degree of killing of the strain by amorolfine was not greater than that seen by liranaftate, and little reduction of the viable counts by luliconazole and ketoconazole was observed irrespective of concentrations of the agents.
| ln Vitro |
Liranaftate has outstanding antibacterial efficacy against T. rubrum conidia. The minimum inhibitory concentration (MIC) for each of these drugs was 0.009 g/ml during a 14-day exposure period. Day 9 saw the beginning of the lignate-induced decrease in MCC, which reached 0.039 g/ml on day 14 [1]. Liranate demonstrated the largest decrease in viable counts of Mucor rubrum below the detection limit in time-kill studies. No matter the drug concentration, luliconazole and ketoconazole exhibited no decrease in viable bacterial counts, and amorolfine did not kill strains more than liranate [2].
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| References |
[1]. Oku, Y., et al., [Fungicidal activity of liranaftate against Trichophyton rubrum]. Nihon Ishinkin Gakkai Zasshi, 2002. 43(3): p. 181-7.
[2]. Oku, Y., N. Takahashi, and K. Yokoyama, [Fungicidal activity of liranaftate against dermatophytes]. Nihon Ishinkin Gakkai Zasshi, 2009. 50(1): p. 9-13. [3]. Maruyama N, et, al. [Suppression of experimental inflammation by anti-fungal agent liranaftate in mice]. Nihon Ishinkin Gakkai Zasshi. 2010;51(1):7-11. [4]. Kobayashi M, et, al. [Anti-fungal drug liranaftate suppresses fungal element-promoted production of IL-8 in normal human keratinocytes]. Nihon Ishinkin Gakkai Zasshi. 2008;49(4):319-22. |
| Additional Infomation |
Liranaftate is a member of tetralins.
Liranaftate is a thiocarbamate and squalene epoxidase inhibitor with antifungal activity. Liranaftate inhibits fungal squalene epoxidase, an enzyme that plays a key role in the synthesis of sterol which is essential for cell membrane integrity. By preventing ergosterol synthesis and causing accumulation of squalene, this agent increases cell membrane permeability, cell leakage and eventually cell lysis. |
| Molecular Formula |
C18H20N2O2S
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| Molecular Weight |
328.43
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| Exact Mass |
328.124
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| Elemental Analysis |
C, 62.77; H, 5.85; N, 8.13; O, 13.94; S, 9.31
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| CAS # |
88678-31-3
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| Related CAS # |
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| PubChem CID |
3936
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| Appearance |
Solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
462.5±55.0 °C at 760 mmHg
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| Melting Point |
98.5-99.5ºC
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| Flash Point |
233.5±31.5 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.642
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| LogP |
5.2
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
23
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| Complexity |
407
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S=C(N(C)C1C=CC=C(OC)N=1)OC1C=C2CCCCC2=CC=1
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| InChi Key |
GTLOCRWOJSGVDM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H20N2O3S/c1-22-17-9-5-8-16(19-17)20(24-2)18(21)23-15-11-10-13-6-3-4-7-14(13)12-15/h5,8-12H,3-4,6-7H2,1-2H3
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| Chemical Name |
O-(5,6,7,8,-Tetrahydro-2-naphthyl) 6-methoxy-N-methylthio-2-pyridinecarbamate
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 25~100 mg/mL ( 76.11~304.48 mM )
H2O < 0.1 mg/mL tert-Butanol : ~11 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.61 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (7.61 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: 2.5 mg/mL (7.61 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0448 mL | 15.2239 mL | 30.4479 mL | |
| 5 mM | 0.6090 mL | 3.0448 mL | 6.0896 mL | |
| 10 mM | 0.3045 mL | 1.5224 mL | 3.0448 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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